Making Remote Work

Making Remote
Work Work
GIL GILDNER

MAKING REMOTE WORK WORK
Making Remote Work Work:
How To Work Remotely & Build Teams From
Anywhere In The World
Copyright © 2020 by Gil Gildner
www.discosloth.com
All rights reserved. This book or any portion
thereof may not be reproduced or used in any
manner whatsoever without the express written
permission of the publisher except for the use of
brief quotations in a book review.
ISBN 978-1-7337948-1-7
Published by Baltika Press
www.baltikapress.com
Printed in the United States of America.
2

Acknowledgements
Thank you to Anya, who works in the other room.
5

Contents
Acknowledgements 5
Contents 6
Introduction 9
How This Book Is Structured 23
Building Remote Teams 26
Putting Together The Perfect Remote Team 27
Who Makes A Good Remote Colleague? 29
Interviewing Candidates For Remote Positions 36
The Importance Of Cohesive Teams 46
Focus On Face Time 54
The Highly Visible Yet Non-Productive 61
Time Zones, Scheduling, & Micromanagement 71
6

Problems Remote Colleagues Run Into 78
Payroll & Salary For Remote Employees 83
Transitioning Employees Into Remote Work 94
The Blueprint For Going Remote 107
One-Size-Fits-All? 109
Team Introductions & Onboarding 113
Finding Remote Candidates 124
Communication Tools & Standards 130
Motivation & Performance 140
Making It As A Remote Worker 147
The Importance Of Structure 149
Working Remotely As A Freelancer 155
Independence As A Remote Worker 161
Finding A Remote Job 171
Personal Downsides of Remote Work 177
Remote Workflow & Communication 189
When Process Gets In The Way Of Progress 191
Removing Time From Productivity 203
Triaging Communication 212
Remote Technologies 219
Best Practices For Managing Employees Remotely 226
An Afterword 232
7

Introduction
The crashing surf from the ocean. The cry of seag-
ulls. A gentle salt breeze. A laptop balanced upon a pair
of nicely tanned legs.
We've all seen this scenario described in countless
articles, sticking out in our minds like a bad stock pho-
to. But here's the deal: these articles are always either for
or against remote work. No middle ground. Like many
subjects, it's difficult to find a balanced and informed
discussion about working remotely. You'll either find an
enraptured freelancer claiming they'll never set foot in
an office again, or you'll find a concerned corporate
middle manager discussing how inefficient his dis-
9

tributed team is.
It's hard to get a realistic grasp on the possibilities
of remote work. As employers, we want the best for
both our employees and our company. When we're
making a decision for our business, we don't want to
fall prey to emotional decisions - we want data to back
it up. We want informed anecdotes from folks who
have experienced this directly. We want to know about
the failures and the successes.
It's great to learn from history. But I think we'd all
rather learn from someone else's mistakes than learn
from our own.
When you're researching remote work, you’ll notice
that there seems to be very little balance in perspective.
I have a few ideas why this is so. Remote work in the
modern world is fairly new, and it's a hot-button topic.
It's emotional. It's cultural. It's somewhat revolutionary.
And it's right in the middle of two playing fields: the
traditional corporate world of enterprise business, and
the roguish new future of solo tech junkies.
So, when we go out there to take a look at the em-
pirical data around remote work, we're instead assaulted
10

on both sides by opinions and biases - and research
studies (on either side) backed by folks with just a little
bit too much investment in their own correctness.
I see more and more articles out there, harping on
the benefits of remote work. I think this new awareness
of remote work is a great thing, but you've got to re-
member that the sample is very biased. Content mar-
keters, writers, and journalists are some of the most
likely professionals to already work from home. Of
course they'll be primarily on one side of the equation:
remote work, after all, has been their norm for years.
On the remote side, you've got a lot of writers,
marketers, and tech junkies claiming that the oﬃce is
dead. Long live the laptop! And on the oﬃce side,
you've got a lot of managers, owners, HR departments,
and investors claiming that remote workers aren't pro-
ductive and increase liabilities. Long live the nine-to-
five!
The reality? Both are right, and both are wrong.
There may not be a single silver bullet that works
for everyone, but there definitely is a best solution for
your own unique problem, and that's what I'd like to
11

explore in this book.
I want to talk about the pros and cons of both
models. In doing this, we'll talk to remote workers,
managers, and business owners who have been involved
in some form with operating within a distributed team.
We'll discuss productivity, challenge some basic as-
sumptions about work, talk about what “work” is any-
way, and explore some of the downsides of remote work
in the context of personal fulfillment, business invest-
ment, career progress, and look at trends to see where
we might end up with remote work after a few more
years.
But let’s back up, and I’ll give you some back-
ground info.
I have personally been working remotely since
2011. Like many who started working remotely before
it was a super popular trend, it started out of necessity
rather than desire. My first internship right out of col-
lege lasted for just under a year, and after that, I found
myself diving directly into the deep waters of freelanc-
ing. Those first few months of post-college freelancing
12

were supported by a side gig as a barista, but after I quit
the coﬀeeshop I never had to report for work at a phys-
ical location ever again.
Since then, I worked for five years as a freelancer
and consultant, then for two years as a remote full-time
employee (a creative director for an airfare company)
and then for the past three years as the co-founder of a
fully remote marketing company.
All of this I've done entirely remotely. As a free-
lancer, I bid for projects and found subcontractors to
hire out, all remotely. As an employee, I was both inter-
viewed and hired remotely, and then interviewed
dozens of new hires myself. And as the cofounder of a
company, I've read hundreds of applications, inter-
viewed, and ultimately hired both full-time employees
and part-time contractors of our own.
Anya and I cofounded Discosloth in early 2017.
From the beginning, we knew our startup would be a
remote company. We met each other while working
remotely, and it had been years since either of us had
worked in a traditional oﬃce. Laying the foundations
13

for an entirely remote company was only natural.
Discosloth started out as a side gig by Anya and I
while we still worked our day jobs. It was a slow first
few months for us as we dove into the digital search
marketing industry, managing and creating Google Ads
campaigns and auditing SEO projects and developing
web analytics solutions. We worked incessantly every
evening to onboard clients and find projects.
Things took oﬀ quickly, however, and within a few
months we were making more from Discosloth than we
were from our normal jobs. We quit our jobs, went full
time, and since then we’ve never looked back. We hired
remote colleagues, first contractors and then full-time
employees. Our client list grew, slowly but steadily, and
we began the long project of diversifying and pivoting
away from a mere services company into a tech-focused
company with multiple streams of revenue. Throughout
the years, we’ve built processes and established best
practices for working remotely, and those practices con-
tinue to evolve.
With that level of remote pedigree, you'd think I'd
be a diehard proponent of remote work. Well, I am and
14

am not at the same time. We'll get into the complexities
later on in the book - it's a very convoluted subject, and
not one you can just make a declarative decision on
within a few minutes. There are potentially massive up-
sides and potentially cataclysmic downsides when
you're dealing with a distributed work force, and I'd
like to approach these factors in as balanced a manner
as possible.
Something to remember is that what we call “re-
mote work” is actually the historical norm. Over the
long course of humanity, the vast majority of people
have worked from home. Going into an oﬃce that was
anywhere further than the shop downstairs was a luxury
reserved only for the most elite. It wasn't until a couple
hundred years ago - a fleeting instant of time in the
grand scheme of things - that people starting going to a
factory or oﬃce. With the advent of the Industrial Rev-
olution in the late 18th century, mass production be-
came an employer of thousands, and the trend grew
well into the 20th century. The advent of fast commu-
nication (like the facsimile and the telegraph and the
steam engine) brought with it the ability to do work
15

outside the traditional limitations of slow travel and
slow communication.
Throughout the twentieth century, this trend con-
tinued to grow, but then the internet happened. Since
we were already going into the office to type on a com-
puter and talk on the phone, we found we could do the
same things from the comfort of home.
For the first few years of the new "remote work",
this work-from-home status was reserved for a very se-
lect few - people like regional managers who traveled to
district offices, nerdy webmasters who started making
good money from running forums and blogs, freelance
writers who could email in their work instead of hand-
ing it in on a floppy disk.
As the internet got faster and laptops got cheaper,
remote work kept growing. Why pay for office space
when you can just work from your home office?
And then, the younger generation who had entirely
grown up surrounded with computers started to get
into the work force. By this time, it was hardly a ques-
tion of how. Today, for the average worker, it's more a
question of why not?
16

There are many reasons why a company might de-
cide to distribute their workforce: added financial sav-
ings, increased timezone coverage, territorial market
expansion, gaining access to a wider pool of skillsets
and workers, improved diversity of ideas, better job
perks, and an almost endless amount of other equally
valid factors.
Financial savings is perhaps the most common of
reasons that a company goes remote. By doing this, a
company can effectively provide a better level of income
to those in the company who live in lower cost of living
areas, from the guys in the C-suite to the folks in cus-
tomer service.
Why do millions of New York workers commute
hours daily from Connecticut or New Jersey? They're
making big-city wages and living in a much cheaper
area, and often their standard of living exceeds anything
but the most fortunate of New York City's natives can
afford. This is an example of remote work on a micro
scale (if slightly inefficient and onerous). You see this
pattern in every large metro area: commuting from
17

Oakland to San Francisco, Rockford to Chicago,
Round Rock to Austin. With remote work, you can
work for a Silicon Valley company while living in the
middle of Nebraska, or on the beach in Thailand. This
income arbitrage, as it's known, is the single most in-
fluential reason why remote work has swept the digital
world by storm. If you can work from anywhere, why
would you pay $4000 for rent in New York City? Half
that amount would get you a beachfront villa in Bali.
Unfortunately, there's a dark side to this. I've seen
more than one company use going fully remote as a
last-ditch effort to save a dying business. Cutting over-
head like offices can be a massive benefit for a company
in a cash flow crunch. But this doesn't make it ideal,
any more than amputating a gangrened leg to save the
rest of the body is ideal. I've seen it happen too often as
a last-ditch effort to induce profitability in a dying in-
dustry, and when this is the case it's hardly the best
long-term strategy from a business perspective.
If you go a little bit further, there's an even darker
side. You don't see it super often, mostly because it's
unsustainable, but an increasing amount of companies
18

use remote work as a form of in-sourcing - bringing
cheap oﬀshore labor into the company as full-time
workers. This strategy operates on the assumption that
you can run a first-world company on workers that cost
four hundred bucks a month. We'll go into this in far
more detail later on, but there's some simple reasons
why it doesn't work in the long term. Good workers are
worth their wages no matter where they're from, and
companies that try to cheap out on payroll quickly
learn that their best remote employees will move on to
somewhere they're paid a competitive wage.
That's not to say that it doesn't make financial sense
to go fully remote: in many cases, it's absolutely the
best decision a company can make. But in order for it
to work, the remote ethos needs to be baked into your
company from the start, not as a last-ditch eﬀort to cut
costs and turn a company around.
Timezone coverage - the ability to have hands on
deck at every moment throughout the day - is another
benefit that is especially unique to certain industries.
Having remote employees spread out throughout the
globe is invaluable to companies, allowing you to keep
19

an eight-hour workday but have constant uptime. This
can be a huge benefit to businesses dependent upon
heavy customer service, high-touch service businesses,
or IT businesses in sensitive industries like healthcare,
security, or finance. Adding just three or four positions
can ensure that the entire globe is covered. It's a rare
need, but one that is perfectly suited for a distributed
team.
Territorial market expansion is another reason. A
rapidly growing global company can't always afford the
immense expense of establishing physical offices in
every new market, and remote employees can be the
perfect antidote to this problem. Instead of spending
tens or even hundreds of thousands on new office
space, HR, company registration, and banking, you can
simply hire regional employees able to travel within the
specified area during launch.
Gaining access to a wider pool of skillsets is a mas-
sive benefit, and perhaps my favorite. If you're operat-
ing in an uncommon niche, finding the perfect candi-
date for a role who both matches your company's cul-
ture, possesses the specific skillsets, and also lives in
20

your immediate area can be a literally impossible task.
Our first full-time hire at Discosloth was remote, sim-
ply because there was no one within commuting dis-
tance who had the requisite skillsets (managing ad
campaigns on the Google and Microsoft advertising
platforms). Not only were we able to get hundreds of
applicants for the position, but we found an employee
who matched our culture perfectly - and was actually
an ex-Googler, on top of that.
Going remote can also vastly improve your diversity
of ideas and operation. We'll go into far more detail
about the upsides and downsides of bringing in more
cultures into your company, but for tech-centric busi-
nesses I can't think of something more valuable than
bringing in people who can shatter the status quo. I've
worked in hyper-local businesses before. Don't get me
wrong: it can work extremely well, especially in a small-
town scenario, because everyone works together like
clockwork. But any expansion outside of that small
town comfort zone becomes impossible, because an en-
tirely homogenous company isn't terribly flexible or
adaptive. Bringing in additional cultures can be the
21

spark that takes you from mediocre to amazing.
Oﬀering a remote workplace is also an incredible
job perk. More and more, as remote work becomes
somewhat normalized within the tech-forward world,
excellent developers and marketers and project man-
agers want to work from home (or from a beach some-
where). The freedom and independence that you're af-
forded with a remote job can be priceless. Giving some-
one the option to work remotely can be the diﬀerence
in hiring the perfect candidate, or getting passed over
for some other company.
22

How This Book Is Structured
This book is divided into distinct sections that ad-
dress diﬀerent issues in the world of remote work. If
you’re a manager or owner interested in building a re-
mote team, perhaps the first few sections will be of in-
terest to you. If you’re an employee at a remote compa-
ny, perhaps the latter sections will be more applicable.
Either way, I think that it’s probably a good idea to look
at remote work from both perspectives, whether you’re
on the management side or on the employee side.
There’s a lot of give and take involved in a successful
remote team. If a single thing is the most crucial ele-
ment of success, it’s independence and ability to com-
23

plete work without micromanagement. This requires a
level of understanding of where each other is coming
from.
First, we will look at the details involved in putting
together a high-functioning remote team: how to iden-
tify individuals who will work well in a remote envi-
ronment, how to best interview these candidates, the
importance of team cohesiveness, the importance of
face time, how to identify remote colleagues that aren’t
pulling their own weight, and then an entire range of
potential team issues including time zones, payroll, and
communication.
Then, we’ll have an entire section devoted to per-
haps the most practical approach to actually structuring
your team: a remote blueprint. We’ll lay out just how
we do it at Discosloth, and what we’ve found works
best. This blueprint section will detail things like how
to onboard new team members, communication tools
& standard policies, and how to focus on motivation
and performance as a remote team.
The next section will focus on being a remote work-
er yourself, and detail the important personal lessons
24

we’ve learned on being focused, maintaining a success-
ful career, and how to alleviate the various problems
that pop up as a remote worker.
And finally, we’ve dedicated an entire section on
remote workflow and communication. It’s notable that
in many remote companies, one of the biggest points of
divisiveness is just how to communicate with one an-
other. It seems like extroverted sales executives prefer
diﬀerent modes of communication than introverted
software developers, for example, so establishing a cohe-
sive and consistent policy of communication is ex-
tremely important. We’ve developed a form of commu-
nication triage, which helps guide a remote team into a
consistent form of talking with each other while being
entirely remote.
25

Building Remote Teams
26

Putting Together The Perfect Remote Team
This section is for the manager, or the business
owner, who wants to go remote.
There are many reasons for this intent - and the var-
ious benefits range from finances, lifestyle improve-
ments, productivity, or simply because it seems like a
good idea.
The good news is, building a remote team is easier
than ever. The bad news, though, is that it’s still a very
unknown field. It’s not a universal practice. There is still
a lot to be learned and a lot to be explored. However, a
few basic lessons can be learned from the experiences of
others that make the path a lot easier for the rest of us.
27

Our experiences have been biased towards the fields
of tech and marketing, so if you’re in a different area of
work you can expect some minor differences. However,
chances are if you’re considering the efficacy of imple-
menting a remote policy in your business, you’re prob-
ably in one of these fields.
Any business in which the personnel spend most of
their time hunkered down in front of a flickering CRT
is a business which can convert to remote work. Al-
though I have spent over a decade working remotely in
the field of digital marketing (all the way from an en-
try-level employee, to mid-level management, to a
business owner) the general policies will apply to nearly
any other industry as well.
28

Who Makes A Good Remote Colleague?
Not everyone is cut out for remote work.
The most positive reason for not being cut out for
remote work is that you simply don't like it. And this is
an excellent reason! For many, going into the oﬃce,
having lunch with colleagues, having a predictable rou-
tine, and interacting with people on a daily basis is very
important. If someone enjoys going to the oﬃce,
they're not going to be attracted to working remotely in
the same way others are.
There are some negative reasons that make someone
a poor fit for remote work, as well. In my experience,
the most negative reason is laziness. Even though it's
29

still very competitive and relatively diﬃcult to land a
fully remote job, it's easy to not do what you need to
do. Nobody's watching you. There's no nosy coworker
in the cubicle next to you, no manager breathing down
your back, no boss who walks through the oﬃce from
time to time.
A successful, long-term, sustainable remote employ-
ee is self-driven, ambitious, and hard-working. They've
got to want to work. And perhaps most of all, they've
got to be extremely independent.
From a macro perspective, independence means
owning the decision-making process in your life, in-
cluding accepting full responsibility for both positive
and negative consequences from your actions. This is
crucial for the remote employee: if they have to be mi-
cromanaged from a distance, they're simply not cut out
for remote work. Taking personal initiative is a basic
essential, and it's something to keep at the forefront of
your mind when you're hiring a remote employee.
In talking to managers and business owners, I'm
told that today's workers aren't very independent. Now,
I'm from a younger generation myself, so I bristle when
30

someone brings up "lazy millennials". I know that's a
generalization, and pretty flat-out antithetical to my
own experience. But I think the basic spark that makes
the middle-aged manager complain about indepen-
dence is real: it’s just not necessarily a generational
problem.
The modern world has brought with it a lot of fun-
damental problems, most of them psychological and
philosophical and far outside the scope of this book.
But I think it's really important to glance at the root of
the problems and wonder if there's a solution.
Ten thousand years ago, it was a lot easier to know
your purpose.
When survival is diﬃcult - when hunting your sup-
per is a matter of life and death rather than rummaging
through the fridge - you don’t have to worry about
ideals. When it’s you versus a sabertooth tiger, you
aren’t too worried about vacation time, health insur-
ance, or compulsory education.
For better or worse, the average run-of-the-mill
prehistoric worker wasn’t complaining about the ambi-
ent oﬃce temperature. The blizzard outside was a little
31

more alarming, and he needed to brave the storm and
gather fallen branches to fuel the flickering fire.
In many ways, although everyday life for everyone
across the world has evolved into an infinitely easier
existence, we’ve developed an identity crisis of self.
Survival - perhaps our most core instinct - is sud-
denly put on the back burner. We wake up and go to
work, type on keyboards, wash down tabletops, screw
down drywall, develop applications, trade derivatives,
make coﬀee, stock shelves, dig ditches, teach class, and
play ball.
We live in a world of automated air conditioning,
thousand-dollar desk chairs, thousand-horsepower cars,
digital currency, private space companies, dental im-
plants, pensions, and lifespans beyond anything ever
seen before.
Yet in the middle of all this, we’re lost. We don’t
have a purpose.
We’re like ants in an anthill, lost amid the swarm of
drones and workers, stuck in an eternal loop of go
fetch. Ten thousand years of advancement has brought
an incredible quality of life to our fingertips. And now
32

we’re coming to terms with this.
So what does all this mean? Simply, that motive is a
very important part of finding a good remote employee.
Why do they want to work remotely?
Finding a good remote employee is extremely diﬃ-
cult. It’s double or triple the work as finding a local
employee. First oﬀ, it's just more rare overall to find
someone who actively desires to work from home or
from abroad. And second, you've got to find people
with such exceptional communication skills that they
are likely among the top few percent of their field - be-
cause they're going to be communicating from a dis-
tance all day long.
Here are a few questions to think about when
you're looking for a reliable, independent remote em-
ployee. There are many answers, and not all of them are
right or wrong. But there’s a few definitely right an-
swers, and there’s a few definitely wrong answers.
What are the definitely right answers?
First, it’s good if they want to work remotely be-
cause they want their work to be directly reflected in a
reward, like how much they make or how indepen-
33

dence they have.
Second, it’s good if they want to do this because
their personal growth and goals are currently limited by
location or employment, and remote work will help
them aﬀord both the time and money to complete
those goals.
Third, they want to do this because they do their
best work when they're making the decisions them-
selves, and it makes them happy.
Definitely wrong answers?
First, it’s a warning sign that they want to work re-
motely because they don’t like working full time. Re-
mote work, after all, is still work. It’s not remote vaca-
tion.
Second, it’s not good if they want to do this because
it’s other people’s fault they haven’t been able to meet
their goals and dreams. In remote work, you must be
extremely responsible for your own faults and failures -
as well as successes! You want self-driven, motivated,
responsible individuals.
Or third, another terrible motive is that they want
to work remotely because they are unhappy, and they
34

think going somewhere else will solve their problems.
The grass is greener on the other side, until you step
across the fence.
Perhaps your candidate's answers line up with one
side of these or the other, or are a mixture of the two.
But the basic premise is keeping a balance between pos-
itivity and negativity: and most of all, self-awareness.
If someone is pursuing remote work because they’re
an ambitious, energetic, independent person who just
wants to work hard and do cool stuﬀ, they’re in the
right boat.
If they’re doing this because they're apathetic or
anti-social, perhaps someone whose ultimate goal is re-
laxing in a hammock with their email open in the
background, their boat will start to sink.
Make sure they've got a doggedly hard work ethic.
That's really the only way of making remote work work
for both the company and the employee.
35

Interviewing Candidates For Remote
Positions
Interviewing is a hell of an art. It's not even a sci-
ence, as you might think: there is something about a
good interviewer that just can’t be universally replicat-
ed. Asking the right questions, probing for truth,
putting the candidate at ease, and keeping a strict agen-
da is something that seems innate with some folks. I'm
always impressed with those who can interview candi-
dates well.
One of my first jobs as a remote employee started
out with a series of interviews with the executive who
would be my future boss. He remains, to this day, one
36

of the greatest interviewers I've ever known. It was
somehow a pleasure to be interviewed by him. He asked
all the right questions, knew how to put me at ease, and
still was able to check off his list of essential questions
without it feeling like a quiz bowl tournament.
I've done my fair share of looking through resumes,
shortlisting candidates, and interviewing future em-
ployees, but I'm no master at this. It can be very diffi-
cult to push through your gut reactions and make a
perfect hire. And to be honest even this executive, the
best interviewer I've met, still ended up making some
big hiring mistakes.
I can’t claim a perfect track record, either. A few
years ago, Discosloth was doing some marketing con-
sulting for a rapidly growing startup. Revenue, funding,
and team was expanding exponentially, and as part of
this growth they needed to hire a marketing director. At
the time their marketing team was completely remote.
Although it wasn't under our direct purview, I was in-
vited to interview a potential candidate who had been
shortlisted, done a great job on a small paid test project,
and was about to be offered a position.
37

I had a short video interview with Talia. She was
familiar with all the right jargon, brought up some
good ideas that jived with mine, was friendly enough,
and had a great history of experience at some well-
known companies. I gave the hiring director my ap-
proval. There were no obvious red flags.
Turns out, Talia was one of the worst marketing
directors we have ever worked with. She was an incred-
ible interviewee, and was somehow able to put on a face
of expertise that immediately melted as soon as she was
hired. We met her in person a few times at the compa-
ny’s onsite meetings. She was grating and awkward, and
I could visibly see her new colleagues become uncom-
fortable around her.
It was as if, upon hiring, she cast off her robes of
humility and feasted upon her power. She sent aggres-
sive emails, spread blame around the office, denied any
problems from her end, started instituting inefficient
policies and processes, and completely nuked marketing
strategies that had been working well for years. She
didn't really have a true understanding of any market-
ing tools. Talking to her was impossible, like talking to
38

a concrete wall. She was inflexible, and not once admit-
ted fault or accepted an alternative strategy to a prob-
lem. It was one of the most shocking about-face trans-
formations I've ever seen in a person, pre- and post-hir-
ing.
Talia had gone through several rounds of inter-
views, projects, conversations, and no flags were raised.
Two months after she started, she had somehow de-
creased the company's conversions by over 11%. By the
end of the year, she’d been fired.
How did someone so objectively terrible at their job
pass this much vetting? Unfortunately, she was inter-
viewed remotely, and I suspect this has a great deal to
do with it. As I learned later, she hadn't fully disclosed
the real reason behind leaving her previous position at a
well-known startup. As it turns out, the hiring manager
hadn't done enough due diligence, and later learned
Talia had been fired for constantly picking fights with
the previous startup’s chief marketing oﬃcer.
Interviewing at a distance is so diﬃcult that I actu-
ally recommend avoiding it whenever possible, at least
in the later stages.
39

The primary reason that remote companies don't
interview in person is because of the cost. It's not cheap
to fly someone halfway around the world and sit down
with them. But then again, neither is it cheap to hire
someone, pay a salary for three or four months, and see
a reduction in company performance on top of that.
Meeting someone in person, feeling out their social
skills, putting them in an unfamiliar environment
rather than the familiarity of their living room, asking
pointed questions, and most of all figuring out if
they're pleasant to be around just can't be done the same
way over Skype. It may cost one or two thousand dol-
lars to fly someone in for an interview, but a bad hire?
This can cost you tens of thousands more.
That's not a very remote-friendly tactic, I know. But
it's the tactic I believe is actually most dependable, and
what I absolutely recommend to most companies.
Of course, it's not always realistic to fly someone in.
Our first few years as a startup simply didn’t give us the
budget to do this with a potential hire. There are some
additional methods to filter out the bad hires, even if
you've never met them face to face.
40

The first is interviewing through a variety of medi-
ums: email, telephone, and video. After all, they'll be
communicating via all these mediums when they're
working for you.
The second is have as many people within the com-
pany as possible have a conversation (not necessarily an
interview) with them.
The third is to have a panel interview via Zoom,
with three or four people from the company discussing
afterwards and submitting a few anonymous comments
and votes.
The fourth is to take your time. The beauty of re-
mote work is that your pool of qualified applicants is
unmeasurably higher than your local pool of applicants.
The fifth (and perhaps the most diﬃcult to imple-
ment, but also the most important) is to really press
them. With remote work, there is a huge buﬀer of time-
zones, distance, environment, and perhaps cultural,
economic, and communication styles as well. Piercing
through this barrier can help identify the true personal-
ity, and sometimes the only way to pierce that barrier is
by really pushing the person into an unfamiliar zone.
41

If I'd have pushed Talia a little harder, I might have
been able to uncover some of those red flags. In retro-
spect, I should have asked pointed questions about the
tools and techniques she claimed expertise in. I should
have asked about negative career experiences she'd had
in the past, and doubled down on that question just in
case. But more than anything, I should have posed
some abstract and conceptual questions to her. Talia
was a laser-focused person, but extremely myopic. She
couldn't understand the viewpoints of anyone around
her, and if anyone disagreed with her she would actually
resort to insulting their intelligence.
It just so happened that in my brief interview with
her, she agreed with most of the company's viewpoints
and strategies, so there was no opportunity for me to
see what happened when she disagreed.
It's not all bad news for remote interviewing, how-
ever. The vast majority of remote colleagues I’ve worked
with (as well as the employees we’ve hired for our com-
pany) are in general much more ambitious and well-
rounded than those in traditional companies.
42

There’s a few reasons for this. First and foremost, I
suspect, is that employees looking for remote roles are
generally by default more forward-thinking, open-
minded, and skilled than the median worker in a tradi-
tional environment. It only makes sense that progres-
sive companies attract progressive candidates. But
there's also the fact that remote companies typically
don't hire generalist roles. They’re hiring specialist roles.
Very few remote companies need a cluster of oﬃce
managers. More likely, they are looking for something
highly specific, like a customer service team manager
with experience in their specific niche, particular
CRMs, support software, and startups. That sort of
employee is going to be a rare find anywhere, but
they're more likely to be looking for a remote role than
a totally unspecialized candidate.
Traditional companies also like to hire someone as
specialized as this, but it's unrealistic in most markets.
In Cleveland, Ohio, there is no realistic chance of find-
ing a local customer service manager who has worked
with SaaS customers, familiar with Salesforce, and has
implemented Intercom support software with a Ruby
43

on Rails-focused dev team.
When the net you cast covers the entire world, sud-
denly you have hundreds if not thousands of potential
employees almost perfectly suited for your needs. If
you're just looking at 30 miles around Cleveland, you
may have only two or three suitable candidates, and be
forced to settle for the one who sucks least.
What does it take to be a good interviewer? Vol-
umes have been written on the subject, and I probably
wouldn't have much value to add to the matter. But I
think remote interviewing, specifically, has some nu-
ances that are only understood if you've spent some
time in remote work.
Reading body language, for example, is a skill that
good interviewers have. It's not so much a science as a
gut instinct of knowing someone is uncomfortable, or
faking it, that they aren't happy right now, or maybe
that this person is genuinely excited about the oppor-
tunity. It's very diﬃcult on a two-dimensional comput-
er screen. You only see the person from chest up.
Maybe not even their hands. It's harder to hear their
44

voice and catch the tiny trembles or wavering notes that
subconsciously clue us in to a deeper meaning. You
can't see what they're doing with their hands, or if
they're shaking their legs.
The disconnect may seem trivial, but it's not. In an
in-person interview, you'd be really suspicious if they
walked into your oﬃce for a morning interview and
you caught a whiﬀ of alcohol on their breath. In a re-
mote interview, for all you know they might be holding
a half-empty fifth of Jack Daniel's underneath the table.
If even large red flags could be missed in a remote in-
terview, there is an even larger number of small red flags
that can be missed.
45

The Importance Of Cohesive Teams
The cohesiveness of your team is important in any
company. The cohesiveness of your team in a remote
company is absolutely crucial: there is no room for mis-
communication. If you think it's easy for management
to be manipulated even in a traditional oﬃce setting
(and it is!) you can only imagine how much easier it is
to manipulate the company when everyone is working
remotely.
A few years ago, I accepted a fantastic position at a
great mid-sized remote company. Excited to jump into
the role, I started getting acquainted with the company,
learning their corporate values and processes, and start-
46

ed getting my feet wet in some projects within the first
couple of weeks.
Despite reporting directly to the CEO and techni-
cally not oﬃcially belonging to any single department, I
quickly found myself a little confused about the hierar-
chy. The company was extremely progressive and em-
ployed some very forward-thinking structures, so grow-
ing pains are to be forgiven. But within a few weeks a
major problem surfaced, and it was mostly to do with a
single team member.
Partially because the company had a very flexible
hierarchy that wasn't clearly defined, and partially be-
cause I was inexperienced and hadn't ever dealt with an
issue like this before, I found myself swept into a
strange game of oﬃce politics. In retrospect I can clear-
ly see the motivations behind it, but at the time I was a
bit naïve.
I'd started jumping into some meetings and inter-
acting with those who I was to be working alongside. It
was a great company, and since everyone was so ac-
commodating and flexible, I let my guard down.
A particular employee (we'll call him Sebastian) was
47

one of those hyper-visible types. You know, the ones
who always create reports, talk a lot in meetings, send a
lot of emails, call a lot of meetings, and log everything
in spreadsheets. He was master of the paper trail and
master of telling everyone everything he'd ever done.
In retrospect, his previous jobs had been in highly
corporate oﬃces, and no doubt he had developed this
particular system of being hyper-visible because, after
all, that's what gets you promoted in the corporate
world. So it's understandable. But when you translate
this sort of employee into a flexible remote role, it sud-
denly becomes toxic behavior for everyone else in the
team.
Things started out fairly innocuously. He called
some meetings, and I attended. They were mostly con-
ceptual meetings, throwing ideas back and forth, but
they began dragging on: thirty minutes, an hour, two
hours. They weren't very productive, but as a brand
new employee I interacted as I thought was appropri-
ate.
Eventually, however, my own projects started spool-
ing up, and I had better things to dedicate my attention
48

on. I declined a few meetings, and that made things get
passive-aggressively ugly. In a few departmental meet-
ings, Sebastian dropped hints that he was pegged for
the new manager of marketing. He assigned me some
grunt work - really inconsequential stuﬀ like making
reports and filling out schedules.
Annoyed by this, especially as I technically wasn't
even in marketing, I kept on doing my own stuﬀ and
explained I'd get to that work when I had time. Talking
to the rest of my colleagues, I found out he'd also been
assigning them projects, in a strange show of macho
authority. And then he requested a meeting with me.
He didn't show up. He requested another meeting, and
he didn't show up to this meeting either. Finally, via
our work chat he asked if we could meet in ten min-
utes. Three hours later, in the longest meeting of my
life, and he had jawed on and on about future plans
and grand strategies, hardly letting me get a word in
edgewise.
Why did I let him do this? Early on in the meeting
he said he was the one in charge of reviewing my per-
formance after my initial three month trial period.
49

I probably don't have to finish much more of the
story for you to get the picture. Of course he wasn't
actually pegged for the marketing manager position.
That went to someone else. Of course he wasn't actually
in charge of reviewing my performance: it turns out
that my direct report, the CEO himself, was in charge
of that.
Sebastian is the picture-perfect representation of
someone who’s simply not fit for remote work. There
are many individual reasons, but chief among them is
that manipulation and toxic behavior is not easily de-
tected in remote teams. It's hard enough to spot in tra-
ditional teams. Separate everyone by a few timezones, a
couple thousand miles, cultural diﬀerences, and a video
screen instead of face-to-face, and you have a Petri dish
ready for the most toxic of employees to thrive in.
In Sebastian's case, he brings to light a few impor-
tant things to look for when you're appraising a team
member's fit.
First, actual productivity and execution. Sebastian
generated documents every single day - spreadsheet af-
ter spreadsheet of numbers, projections, strategies, and
50

ideas. The only problem was, it just looked important.
He actually completed only one or two projects in his
entire year at the company. His paper trail, however,
kept him in the position far longer than he should have
been. Anyone more than once removed from him as-
sumed he was a crucial part of the marketing team.
Second, manipulation. It's never good to have an
employee who manipulates others, who plays the game
of oﬃce politics with destructive results, and who takes
advantage of other employees. Sebastian's specific tac-
tics were a strange psychological play. He used up hours
of his colleague's time, asserting his authority in an ex-
tremely passive way that was hard to put your finger on.
He also had a knack for playing information against
others, by calling both individual meetings and all-
hands meetings. Sebastian also tended to dominate
screen time, appearing anywhere you looked. We could
wake up, log in, and find chat messages, a couple
emails, and notifications that he'd made comments on
a few spreadsheets and documents. He was everywhere
without being anywhere.
And third, but definitely not least, outright toxic
51

behavior. Threatening to ding your performance review
without even having that role is a dirty trick in my
book. Pitting team members against each other is
equally dirty. Undermining projects, wasting time, and
pushing agendas just to cement his position as a
"leader" is also pretty dirty, considering the company
was paying him for this time.
So what happened with Sebastian, the manipulative
team member? He played his hand a bit too far and
three team members independently complained about
him. Luckily, the complaints were heard. Sebastian
suddenly wasn't the marketing manager. The next week,
actually, he wasn't to be seen at all.
When you suspect that, perhaps, there are some
phantom ineﬃciencies floating around your depart-
ment, it might be time to take a step back and look at
each team member and analyze their actual productivi-
ty. Not what they have proposed, but what they have
actually done. A long-term, bird’s-eye view of someone’s
projects is the best way to look at this. Everyone has
slow periods, so you can’t just look at the past few
weeks. What have they actually finished over the last
52

quarter? What project was actually successful? What
proposal actually found it’s feet and started gaining
ground? Which sales were made, which clients were
gained?
Somehow, in a confusing twist to this story, a few
months later I got a recommendation request on
LinkedIn. I did a double take - it turns out Sebastian
had sent a long message asking for a recommendation
for his work “leading the marketing department.” I
don't always understand people. They're such a mys-
tery, aren't they?
A cohesive team is crucial to both the department’s
health and productivity in the short term, and the en-
tire company’s health and productivity in the long
term. Make sure everyone pulls their weight equally.
There will always be high performers and low perform-
ers, and that’s natural. What you don’t want is a low-
performing outlier: because someone who pushes their
work around to everyone else, and just creates more
busyness all round, is even worse than a mere under-
performer.
53

Focus On Face Time
I remember the first time I saw someone FaceTim-
ing on their phone. It was sometime in 2010, just after
FaceTime was launched, and a college girl was holding
her iPhone at arm's length as she walked down a hall-
way, chatting with someone on speakerphone.
Like the idiot I am, I actually stopped in my tracks
and turned as she passed me, awestruck that Star Trek-
level technology was now available to the common col-
lege student. A decade later, this seems commonplace,
but it's incredible how fast things have changed. I don't
think we realize just how quickly we adapt to new
technologies and take their existence for granted - even
54

if we haven't learned how to best behave with them.
One of the first things I hear from remote compa-
nies is how important video conferencing software is for
communication. And that's obviously true: it's a deal-
breaker for many teams. But I see a common fallacy
developing as well: in the quest for global distribution
and cost savings, companies have also assumed video
conferencing is a perfect replacement for actual physical
presence.
However, it's not.
I have hired people without meeting them in per-
son, and thankfully most of these hires have turned out
amazingly well. Yet I've also participated in hires that
haven't turned out so well, and after meeting them in
person the reasons became obvious. I don't know what
percentage of gut feelings you lose through a video link,
but I would venture to guess that it's far, far higher
than any of us imagined.
I remember helping a client onboard a remote em-
ployee that they had hired to head up their customer
growth department. The first few Skype meetings were
pretty innocuous. The candidate didn't raise any major
55

red flags, and since the company had really already
made their hiring decision, I gave an informal thumbs-
up. This didn't turn out so well. The candidate turned
out to be impossible to work with, and our team (all of
which had conducted pleasant video meetings with her)
were dazed and confused at how impossible this person
was to deal with.
A few weeks later, at a dinner with the client, we
met her in person. Behaviors that had been totally in-
visible or excusable on the video screen popped to the
surface when you were sitting across from her at a table.
Awkward conversation you might blame on a poor
video connection was suddenly right there, staring you
in the face. Personal bluntness that might come from an
unfamiliarity with video meetings (which happens
sometimes) was suddenly extremely rude. What I
thought were attempts at humor on Skype was actually
a nasty sarcastic streak. Basically, these little individual
behaviors, all of which were essentially invisible or for-
givable in a video meeting, added up in real life to a
person who was just flat out mean.
It's not always possible to meet candidates in per-
56

son. Financially, flying in every qualified candidate is an
expense that most small businesses would be hard-
pressed to justify. From a time perspective, that can add
an extra week or two to a hiring process that might al-
ready be behind schedule. But if it is ever possible, and
you're invested in hiring a candidate who is with your
company for the long run, I can't think of something
more important to do.
Once you've hired the candidate, of course, and
you're operating a remote team, it's important to re-
member that you can't just keep operating without
meeting each other in person. Many companies, espe-
cially those in the tech sector, have implemented annual
or even quarterly in-person retreats and meetups. I
can't think of a better way to bring a team together.
One of the biggest objections, again, is the financial
investment required in bringing your global team to-
gether in one place for a few days. And it's not cheap.
However, I recommend taking a look at how much you
save as a company by operating remotely (either by
your savings on salaries, oﬃce rent, or commuting) and
apply that towards the cost of an in-person retreat.
57

Having real-life, in-person interactions with your
team is vital to growing a healthy organization, but it’s
not always possible. There are constraints that come
along with a young company, and the financial costs of
flying your team around the world can be considerable.
However, it’s probably not more expensive than the al-
ternative of keeping a physical office with your employ-
ees in a central location.
Even a long-term traditional office lease can cost
tens of thousands a year at minimum. Talking to a
small business owner in flyover country, I learned that
he was paying $18 a square foot for an annual lease. For
the twelve employees housed in two respectable but
small offices, they were paying upwards of $45,000 a
year for office space. If, instead, that budget was applied
towards travel expenses, suddenly remote work starts
making a little more sense. Not all employees need to
travel often, but even if they did, going remote and sav-
ing $45,000 a year on office leasing would free up a
budget of $3,750 per person annually for flights and
hotels…an amount that would cover at least two or
three typical trips anywhere in the world.
58

And that’s on the extremely frugal side of things. At
one of my first jobs out of college, we had around
eleven employees working out of the headquarters (with
around 20-30 total employees scattered across two
states). The main office had a rent budget of $10,000
per month - just over $120,000 a year. For a small
company that’s a big number, and to be entirely honest,
it would have made more sense to distribute the work-
force and gather them together on a quarterly basis
(none of us made a very competitive salary, since it was
a startup, and we were located in a high cost of living
area in the United States). That’s not to mention inci-
dental expenses associated with an office. Things like
$45,000 for office furniture, weekly lunches, coffee, the
rest.
When it’s not possible to gather people together on
a consistent basis in real life, there are secondary alter-
natives which are almost as good.
Video meetings never quite cut it, as we learned in
our experience with onboarding our client’s terrible new
customer growth manager, but it’s a step in the right
direction. The key is to pair this with many different
59

sorts of communication formats: email, chat, phone,
and hopefully in-person meetings as well.
We have discovered that the schedule and format of
video meetings has a lot to do with how people interact
and show their true colors, and this comes to the sur-
face especially in the hiring process. Having a mix of
structured and unstructured meetings can help people
with diﬀerent personalities express themselves comfort-
ably (or uncomfortably, as the case may be). In a long-
term environment with multiple employees working
together, one of the most important strategies is having
meetings with no specific purpose other than to social-
ize. Spending 30 minutes on nothing other than chat-
ting about your weekend may seem wasteful, especially
in the eyes of corporate bean counters, but in reality
having some form of watercooler talk enables colleagues
to develop a rapport with each other that would other-
wise be impossible in a remote work environment.
60

The Highly Visible Yet Non-Productive
Somewhat counter-intuitively, the more important
a single individual is to an organization, the harder it is
to measure their contributions in a quantifiable way.
That's because what they're oﬀering is diﬃcult to mea-
sure. They're not just eyeballs on a screen or fingertips
on a keyboard: they're the voice of the organization,
getting things done, making moves and executing im-
portant strategies.
Companies try to measure productivity, perhaps,
more than any other performance metric. It's such an
essential part of an employee's importance - actually
getting things done - that it makes sense.
61

Of course, I think many people would agree that
most methods of measuring productivity are extremely
broken and outdated. Unless you're running an assem-
bly line, it's diﬃcult to quantifiably measure an indi-
vidual's importance within the organization. Yet that
doesn't mean it's not crucial to the overall health of
your team.
Unfortunately, most of these measurement methods
are so tied to numbers that it becomes easy to game the
results. This is corporate America at it’s best - you end
up having a lot of middle management punching the
clock, issuing reports, and looking at questionable per-
formance stats.
Looking at how many spreadsheets someone creat-
ed, how many emails they sent, or how many phone
calls they made is a wildly inaccurate measurement of
true importance to an organization. You just can't
quantify value like that. The only time you can really
quantify value is when you're looking at the people di-
rectly responsible for sales, but that’s because a dollar
amount is tied to them, rather than mere actions.
In remote work, you have to keep a careful eye out
62

for the highly visible, yet non-productive.
Perhaps you'll remember the fellow I called Sebast-
ian, the former coworker who didn't work out very well
as a remote employee. He was the master of high visi-
bility. The amount of reports he could generate was
staggering. The amount of people he could copy on an
email was impressive. The amount of documents he
created in shared company folders was equally amazing.
The amount of face time he got in meetings outstripped
everyone else. Yet ultimately, even in his mid-level role,
he contributed far less value to the company than even
the newest customer support hire. He didn't produce
anything except paper.
A fellow like Sebastian is diﬃcult for managers to
recognize immediately. And this is because these sorts
of workers are masters at manipulation. Even his im-
mediate coworkers might not be able to put their finger
on it at first, they just have a general feeling of malaise
and a profound unhappiness with him. Most people
won't do anything about it, however, in the interest of
professionalism. After all, if a Sebastian type is smart,
63

he'll never overreach. He'll do just enough to be visible,
yet little enough to never oﬀend or step on toes. He'll
just be there. A lot.
And of course, in a remote role it's even more diﬃ-
cult. When you're working remotely, you can't just
walk down the hallway and see someone hard at work.
If a remote worker is focused on some important work,
you actually won't hear from them. They don't have
time to update the Slack channel or send out an email.
For better or worse, most managers with hiring ca-
pabilities (which may or may not be the C-level, de-
pending on your organization’s size) are a step or two
removed from day-to-day contact with these spread-
sheet warriors. They just see the reports. They don't
have to depend on Sebastian for daily collaboration or
actual results.
In a remote company, it’s crucial to break through
these barriers. As a manager, you can do this in a few
ways.
First, schedule some regular face time with everyone
under you. Even if ten, twenty, or thirty people work
underneath you, if you go weeks or months without
64

talking to them all, this just creates an unneeded dis-
tance between the decision maker (you) and the prob-
lem (a visible yet unproductive employee). Encourage
everyone under you to discuss problems and concerns.
The reality is that companies are hierarchical - even the
flattest of flat organizations - and most issues don't flow
up through the strata to the person who most needs to
hear it. It's a simple yet diﬃcult issue of ensuring trans-
parency and honesty throughout the company. Talk to
managers underneath you, and have them encourage
the same level of communication underneath them.
And don't be afraid to reach out individually to em-
ployees to find out problems - even if that might be a
rogue spreadsheet warrior who isn't pulling their
weight.
Second, keep an eye out for the highly visible: the
employees who generate countless amounts of commu-
nication. Learn to diﬀerentiate the merely extroverted
and prolific from the bullshitters. There is no produc-
tive reason to generate multiple performance reports a
week, to write emails as long as mini-novels, to domi-
nate a Slack channel, or to call a disproportionate
65

amount of meetings. Unless someone is actually serving
solely in a manager role, and is funneling along an en-
tire team, generating a huge amount of paperwork is
doing nothing but slowing the rest of your colleagues
down, and wasting company money in the meantime.
Third, emphasize the importance of clarity, brevity,
and respect of time to your entire team. Discourage fre-
quent meetings that call multiple people together. An
hour-long meeting involving four people doesn't cost a
single hour of lost productivity time, but four hours -
not even including the prep time and distraction from
the real job.
And fourth, having a regular and established report-
ing process in place removes the need for other people
in the company to create their own process. If you've
already got a monthly performance overview process
that works smoothly, it is entirely unnecessary for the
visible-yet-unproductive to create their own reports.
This makes it easier to identify unneeded filler work.
And fifth, but perhaps most importantly, establish a
regular and universally understood performance review
process. Focus not on game-able numbers, but actual
66

results. Say you hold one of these reviews once per
quarter - in a performance review, don't focus on tasks
done, emails sent, leads captured, or strategies concep-
tualized. Focus on actual results and integration with
the team - how does the employee relate to the compa-
ny's profits this quarter? How did the employee con-
tribute to the greater team goal? Did the employee
work well with others and make meaningful contribu-
tions to projects? How many projects did the employee
successfully kick oﬀ and complete?
Of course, sales-focused team members are much
easier to work with - and they’re much less likely to be
able to fake their way through a job. When your prima-
ry measurement of performance is dollars, it's suddenly
a lot harder to explain away by generating a lot of
emails and reports.
It's almost always middle-level employees that are
able to game results. An entry-level employee is usually
graded on tasks, and these tasks can usually not be easi-
ly faked. Higher-echelon team members have added
responsibility and larger outcomes, and are usually
working in tandem with the executive team and outside
67

clients. A middle-level employee, insulated from out-
side contact, and having a good degree of self-direction
and independence within their job role, are almost al-
ways the culprits.
Unfortunately, this describes the vast majority of
remote roles. By definition, a remote role will almost
always have a large degree of self-direction involved,
and this increases the risk of attracting spreadsheet war-
riors.
The sort of spreadsheets that Sebastian generated
were of no particular practical use, but were cool to
look at and exhaustively designed. He would create
spreadsheets with names like "3 Month Sales Outreach
Strategy" or "Customer Journey Study" or "Five-Part
Funnel Analysis". None of these were ever implement-
ed. Most, I discovered, were templates which had just
been copied from somewhere oﬀ the internet and ad-
justed to our company’s specific market. The meetings,
which often dragged on to lengths of two or three
hours, had no clear agenda and were usually called
“brainstorming sessions”. When assigned with an actual
task with an actual deliverable, it would take weeks to
68

get something back from him. His emails were long
and took a long time to parse, but ultimately didn't
really have anything of substance.
Sebastian, it seems, was the ultimate paper-pusher.
He was the master of being visible without producing.
Be sure, when you’re working with your team, that
they can eﬃciently communicate potential problems
like this. It’s sometimes very diﬃcult for a team mem-
ber to “tattle” on one of their colleagues. And under-
standably so - it’s not very courteous and it’s often un-
professional. Regardless, make sure the channels of
communication are open and that your entire team un-
derstands that clarity and transparency is important to
the company’s bottom line. If you start to identify po-
tential problems, it’s better to address it immediately
rather than let it fester.
One of the complex social issues in a remote team is
that when problems arise, they can easily fester in se-
cret. Because there isn’t an easy way to gossip over the
watercooler, and because it’s not very easy to pick up
unspoken hints and body language, you might go
months without knowing that the entire department
69

really can’t stand the new hire.
There isn’t any way to solve this other than com-
munication. In many cases, if you don’t ask, you will
never know until it’s too late.
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Time Zones, Scheduling, &
Micromanagement
Early on in Discosloth's history, back in those mea-
ger first few months when we were eager to take on any
sort of work that came with an invoice attached, we had
an agency client located in Australia.
We work quite extensively with Australian clients,
so this isn't unusual. But the tricky part about Australia
is that it's somehow eternally twelve hours out of sync
with the entire rest of the world. It doesn't matter
where you are, it seems like Australia is always asleep
when you're awake, and awake when you're asleep.
Most of our clients understand this, but not this
71

guy. Our point person, Ian, was one of those guys who
just didn't understand time zones. We were doing two-
week-long website audits, not the sort of project that
requires instant urgency and attention. Yet Ian seemed
to think that if we didn't answer the phone at 3 o'clock
in the morning, we weren't working on the project and
something was going hideously wrong. I remember
waking up to 3 emails, 2 missed Skype calls, and about
a dozen missed phone calls, all revolving around a
project that was going well and didn't need any signifi-
cant attention.
Ian was the sort of client that required constant at-
tention. He sought out feedback on every step of the
way, wanted us to keep a spreadsheet updated daily
with progress reports, and called meetings every time he
had a question.
He sounds like the worst sort of first date.
Ian is not the sort of client that you can manage
sustainably in any way as a remote agency. I'm not sure
you can really manage a client like him in any agency,
but when even a tiny bit of a time diﬀerence comes into
play with a control freak, it multiplies the problems a
72

hundred times. Someone who requires instant attention
cannot work remotely.
Time zones and time diﬀerences in general are
rarely the cause of problems themselves. They merely
serve to make bad communication worse. In most cases
where we've seen problems pop up, and assumed it's
because of a large time diﬀerence, it's actually because
of something like micromanagement or poor commu-
nication.
Rarely do time zones cause crucial problems. More
likely, they just turn up the volume on existing issues.
Working with someone like Ian, who micromanages
and obsesses over every step of the process, might be
bearable in a traditional work setting. In a traditional
work setting, more confounding factors come into play.
First, you'd really only see him from nine o'clock in the
morning to five o'clock in the afternoon. Second, body
language would be muchmore apparent. And third, dis-
tance magnifies micromanagement. This is a psycholog-
ical issue: by definition, micromanagers love control.
They manipulate their surroundings and don't like
when extra layers are put in between them and their
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subjects. Simply put?
Micromanagers hate the concept of remote work.
There will always be a level of importance to time-
sensitive projects and processes. Keeping a web server
up and running requires attention now, regardless of
time zone. Getting an urgent rush project done by the
deadline doesn't take anyone's time into account. Indus-
tries like healthcare or finance with a broken API can't
really wait around for a programmer to show up at his
convenience, Bali time. However, these projects are a
minority, and most of us operate on a scale of weeks or
months rather than days or hours. If time zones are cre-
ating a major workflow problem for the typical mar-
keter, sales agent, financial advisor, mechanical engi-
neer, writer, or web designer, then you've likely got a
communication or scheduling problem instead.
Time zones actually have the ability to create natu-
rally-occurring asynchronous communication, which in
my opinion might be one of the most eﬃcient methods
of work to ever happen. This is when each individual
member works on things separately, rather than all to-
gether, but combines their eﬀorts in a way that doesn’t
74

depend on time.
One example of good asynchronous work is open
source software. A popular, well-run open source
project usually keeps the source code available on a
platform like Github for users to freely fork, work on,
and submit push requests. There is little formal struc-
ture or regulation about how folks contribute their
code: they just do.
When the leader of the project sees good code, it’s
accepted into the project and becomes part of it. It
doesn’t matter whether the code was written at mid-
night, at noon, in South Africa, or in New York City. If
it’s good code, it gets included.
A remote team should work similarly. There are al-
ways times in which you just have to sit down together
and work simultaneously, but rarely. That’s usually only
necessary with extremely difficult problems or very ur-
gent issues. Otherwise? Working separately and then
spending a little time combining your efforts can be
one of the best ways to get quality work done, fast.
A few years ago, I was on a team that worked excel-
lently, perhaps one of the most efficient teams I’ve ever
75

been on. Of the three members of the team, two were
in Europe and I was in the United States. There was
very little overlap in either working hours or roles. We
all had drastically diﬀerent functions: developer, mar-
keting lead, creative director. Yet, once a day we met up
and traded ideas and made sure everything synced up.
During the few months that we worked together,
we blew away all of our team’s targets. Our metrics
looked amazing, and we were getting more traﬃc, sales,
and leads at historically low costs.
There isn’t really a secret to how we did this. We
just happened to be extremely compatible workers who
enjoyed listening to each other and who weren’t locked
in any sort of power struggle. The only way to replicate
this is to match personalities, and I’m not sure this is
consistently replicable anywhere in the world: it either
works or it doesn’t.
Micromanagement is something that happens as a
byproduct of a bad team. There’s a mismatch some-
where that needs to be fixed.
Commonly, it’s assumed that micromanagement
comes from a bad manager. That’s often the case. But it
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can often come from a bad employee who needs mi-
cromanagement.
Either way, it’s a detrimental form of work and
won’t do a small business any good. It’s a drain on re-
sources, productivity, team morale, and overall eﬃcien-
cy. If you’ve got an overbearing manager whose fingers
are in every pie, every single one of those pies will be
half-hearted pies cooked by frustrated bakers. If you’ve
got an employee who can’t find the independence and
self-direction to do their own work, your pies will be
micromanaged to death, and the master chef will end
up doing all the work anyway.
77

Problems Remote Colleagues Run Into
It’s important to understand the everyday struggles
your employees will be facing (timezones, connectivity,
cultural schedules, stuﬀ happening at home).
On one hand, your employee has the responsibility
to create a professional work environment for them-
selves. Along with their freedom to work from any-
where, they also have the responsibility to make sure
they can get their work done eﬀectively without dis-
turbing others on the team.
But, both parties have an obligation to respect each
other during the work day. While it’s rude and incon-
siderate for an employee to work from a distracting en-
78

vironment (appearing on video in pajamas, thumping
music, crying babies, a cluttered background) it’s equal-
ly inconsiderate for the employer to demand meetings
late at night, to monitor employee screens, require
them to clock out for smoke breaks, to institute dracon-
ian dress codes, or similar policies.
Especially when hiring an employee from a diﬀer-
ent culture, you’ll run into some cultural variations that
are important to remember. Many of these are the same
issues that arise in the typical corporate workforce (a
German company will likely be confused by an Ameri-
can employee’s cordiality and familiarity, just like an
American company will be confused why a Colombian
employee treats deadlines as flexible) and thus just re-
quire some common sense to work through.
Some cultures adapt to remote work far more easily
than others. Traditionally cold and distant cultures will
have a hard time adjusting to the friendliness of col-
leagues from warmer cultures, and flexible cultures will
have a hard time adjusting to the goal-based demands
of the typical remote company. Employees from other
jurisdictions will have to adjust to not expect the same
79

benefits oﬀered by domestic employers. For example, a
German remote worker employed by an American
company cannot exactly expect to get the German legal
minimum of a year of maternity leave with full pay…or
two year’s leave if they have twins.
At Discosloth, we are a search marketing company.
We run ads on digital platforms (primarily Google Ads,
but also Microsoft Ads, LinkedIn Ads, and Amazon
Ads) for companies who either sell products or services
online.
We operate in an incredibly narrow niche. Not only
is the field of digital advertising constantly evolving,
but true experts in the field are few and far between.
When we were first hiring for Discosloth, I wasn’t even
sure we could find who we were looking for. There
wasn’t even anyone in our area who I thought was qual-
ified at the proficiency level we were looking for. Even if
we did find someone, I’m not sure we could have con-
vinced them to leave their position to take a chance at a
tiny search marketing company that just started up.
We were forced to take our search to the entire
world. And that’s fine, because we had started the com-
80

pany remotely in the first place and knew to expect this.
Finding qualified candidates for a niche role is an
entire ordeal of its own, but when we finally found our
candidate and made an oﬀer, we knew we were going to
have to adjust to their expectations. Our first employee
lived in Europe and had not previously worked remote-
ly. Previously working for Google as a campaign man-
ager, she had expectations for vacation and benefits that
weren’t standard for the United States.
Compromise was essential, and we were happy to
put together a contract that both gave her a decent va-
cation package, and a significant pay raise (the good old
American benefit).
Ultimately, it’s important that the company strive
to reach a level of understanding with their employees,
and it’s important for both sides to be flexible above all
else.
It’s harder to separate life from work when you’re
working remotely. A company needs to understand this.
If a kid runs into the room during a video chat, that’s
not the end of the world and the company needs to
both expect and embrace the fact that their employee is
81

working from home. At the same time, an employee
who never sets boundaries and structures their work
day appropriately is only harming themselves and the
company.
82

Payroll & Salary For Remote Employees
How do you determine pay for a team that's spread
around the world, with diﬀerent costs of living? Wel-
come to one of the most loaded and controversial sub-
jects in the world of remote work!
Do we pay employees solely based upon location? If
they’re remote, what if they move to London or New
York City? Do they need a pay increase? What if they
move to somewhere in the middle of Nebraska to save
money - do we pay them less? What if someone is from
Cambodia - do we pay them Cambodian wages?
There are some interesting ethical questions which
are out of the scope of this discussion, and probably
83

can’t ever be clearly delineated, but there’s still a lot to
be unpacked from a practical perspective.
A few years ago, I had a role in a fully distributed
company that had employees working remotely across
dozens of countries. Although the vast majority of em-
ployees were American, there were also employees in
Thailand, Scandinavia, the Philippines, Romania, Aus-
tralia, and scattered elsewhere throughout Europe.
The company had recently gone through some fi-
nancial diﬃculties, a change in ownership, and restruc-
turing, so they were in cost-cutting mode. Almost all
new employees were hired from lower-cost countries,
and they gave up their expensive oﬃce lease in San
Francisco.
The company did what is very typical, and paid
wages at local rates rather than American wages.
It’s one thing to find great employees at local wages,
but it’s another thing entirely to retain them. If they’re
good enough to successfully work for an American
company, and thrive in their career, guess what: they’re
going to want American wages. If they don’t get them
at your company, they’re going to get them somewhere
84

else.
Paying local wages works for low-responsibility po-
sitions like customer service or data entry. Paying local
wages also works for higher responsibility positions, but
only for a short time. In my situation a few years back,
what the company found out very rapidly is that when
an employee is performing well, they expect to be com-
pensated accordingly.
Within a couple years, this strategy of paying bot-
tom dollar for talent started to backfire. Specifically,
one of my colleagues started out at a fairly low-level
position at a salary of $1500 per month. Great wages
for her local area, but pitiful wages from an American
perspective. She was an excellent employee. Within two
years, she had saved the company hundreds of thou-
sands of dollars, been promoted several times, managed
a department, and was on the executive team. Yet she
was still making less than $30,000 a year.
That was still a very respectable wage for her local
area, but less than most of the American customer ser-
vice agents were making. Things suddenly got weird
when she started managing new entry-level employees,
85

who would be hired in at $36,000 or so.
Companies are entitled to pay whatever they feel is
fair for the position. However, employees are equally
entitled to leave for greener pastures. And that’s just
what our colleague did, and ended up tripling her in-
come in the process. This wasn’t an isolated event for
this company: successful employees from low-income
countries kept leaving. And leaving. The turnover was
insanely high: developers, customer service agents, and
managers alike all departed for higher salaries. In the
end, the company was left with only the employees who
didn’t want higher salaries.
Is that the sort of employee a company wants? The
idea looks great on a balance sheet, but in reality you’ve
lost your most ambitious, driven, and goal-oriented
colleagues, all in the name of short-term profits.
At Discosloth, we’ve found ourselves caught in the
middle of this struggle as well. Especially for the first
few years, we were a young and lean startup, without a
massive budget for competitive salaries. We were faced
with a challenge: do we pay based on need? Or pay Sili-
con Valley level salaries? Or something in between the
86

two?
I don’t really feel comfortable with the idea of pay-
ing salaries based on need. It’s something that I’ve been
faced with myself, in my role in the same company ref-
erenced earlier. At the time, I was a young creative type
living in Little Rock, Arkansas - not a place known for
an expensive cost of living. During my initial salary ne-
gotiations, my location was referenced as a factor in
determining the amount. It came back up a year or so
later when it was time to discuss a raise - rent was cheap
in Little Rock, so did I really need more money to live
comfortably?
Today, as an employer, I don’t want to perpetuate
that mindset. I’d like nothing more than for our em-
ployees to become millionaires and retire in luxury.
That might not be realistic for all, so we have to find a
middle ground. We can’t aﬀord to pay Silicon Valley
level salaries, but we can do the best we can. Retaining
employees, after all, is important to us. Just like finding
new clients, it’s hard and expensive enough to onboard
new folks, so I’d rather keep what we have than con-
stantly be trying to find more. Our employees located
87

in lower-income countries currently make around four
times the average salary for their locale. Do they need to
make four times the average wage? No, not really. But
do they like to make four times the average wage? Abso-
lutely.
Ultimately, I strongly believe that this issue is re-
solved organically through the free market.
Remote work is a competitive field, both for com-
panies and workers. Only the highest-performing and
ambitious individuals are usually qualified to maintain
most remote jobs, and only the most well-run remote
companies will retain their employees without a high
rate of turnover.
When an employee has the option of choosing any
company across the world to work for, suddenly they
have a much higher salary range to choose from. In to-
day’s market, you can no longer get away with paying a
Ukrainian developer a minimum amount - perhaps it’s
still less than you’d pay in San Jose, but it’s definitely
not a trivial amount. That’s the free market at work,
and I fully expect it to continue flattening the playing
field of salaries, as remote work becomes more popular
88

across the world.
Going remote can make excellent financial sense for
a company, and it's one of the most compelling factors
in choosing to take your team to a distributed mode of
operation.
I'm an enthusiastic proponent of remote companies
for just this reason - however I always hedge it with
some caveats. Reducing expenses and overhead allows
for greater flexibility with business goals. But lower ex-
penses seem often to be used as an excuse for a barely
profitable company to get by. In reality, the ability to
save on office space should give you the ability to spend
a little more on solving the problems that come with
being remote. Otherwise, you can suffer productivity
and morale problems that ultimately cost more than
office space.
But back to rent.
Commercial rent is one of the highest ongoing op-
erating costs for American companies, with a national
price average ranging between $2-5 per square foot -
and that's each month.
89

In a survey of Y Combinator startups, the median
company had only ten employees yet paid an average of
$6,100 a month in office rent. Of course, due to the
type of companies typically going through the venture
capital process that's a higher price than average, but
isn’t an abnormal cost associated with startup compa-
nies in larger cities.
In New York City, it’s even worse. The average cost
of office space per employee is a staggering $14,800
annually…and that counts all businesses, not just tech
or financial startups.
While this is a necessary and affordable cost for
thousands of companies, it's a massive amount of over-
head for smaller or just-starting companies. The
amount of capital required to start a company with tra-
ditional office space creates a large and looming barrier
to entry. And rent is a relatively small part of the office
equation, too. Consider the furnishings, office supplies,
and collective time and expense for commuting for each
employee, and you've suddenly got a much higher
number.
Nixing the physical office completely doesn't work
90

for all companies. While I suspect most companies in
the world can manage to have at least some portion of
their employees work remotely, very few industries can
actually be entirely remote. Many companies still de-
pend on face-to-face interaction with vendors and sup-
pliers and clients, even more companies serve a regional
area with physical goods or services, and even more are
traditionally brick & mortar (restaurants, retail, service,
and supply businesses). While a hospital may be able to
shift the IT and marketing staﬀ to a somewhat remote
role, it's unlikely that hospitals will ever be replaced by
something less centralized.
However, most white-collar roles - sales, marketing,
tech, logistics - are entirely distributable, and that's
where we will see an increased trend towards remote
positions. Companies that operate heavily over the in-
ternet are easily transitioned to a remote-centric struc-
ture, and you may be able to shift the company away
from the oﬃce without even a ripple visible to your
clients. In these cases, the cost savings can be signifi-
cant.
It doesn't come as straight profit, however, and this
91

is worth digging a little deeper into. Although you may
save both your company and your team money by elim-
inating the oﬃce and the commute, you can't just send
them oﬀ into distance and expect everything's taken
care of. As we've covered elsewhere, I don't think teams
operate well under a permanently long-term, long-dis-
tance structure. It's sort of like long-distance dating. If
you don't see your significant other in real life every
once in a while, it's not really dating, is it? You should
expect to spend some of your rent money on annual
retreats or, at the very least, flying in your team mem-
bers to a central location every once in a while.
It also might be nice to give your team an allowance
for remote work, whether that's a hundred bucks a
month to apply towards fast internet, or an equipment
allowance since they'll likely be using their own com-
puter to do your work. Solid, dependable internet and a
good computer is essential for productivity and connec-
tivity. Just because you think your employee ought to
have a good computer and internet connection doesn't
mean they will, and if you transition to remote work
expecting them to use their own equipment and inter-
92

net, you should also expect to pay for it.
93

Transitioning Employees Into Remote Work
When an employee is transitioning into a remote
team, they’re coming from one of many possible back-
grounds.
If entry-level, they might be coming directly from
college or high school and have no significant work ex-
perience at all. In this case, there’s not a whole lot of
transitioning to do. For them, all work is new.
If they’ve been in a career for a few years, they’re
either coming from a traditional, sit-down employment
model, or they’ve already been remote. The traditional
model is most common, and is where most members of
a team will have come from.
94

Employees who have come from previous remote
roles, however, aren’t all perfect. They can come with a
particular set of challenges. They’ve either come from
an organization exactly like yours and will fit into your
team like fingers into a glove (unlikely and improbable)
or they’re coming from either a corporate or freelance
background.
Freelancers have a unique position of both being
well adjusted to remote work, and diﬃcult to embed
into a full-time team. A lot of close attention and care-
ful onboarding has to be given to these freelance sorts,
and I say this as a former freelancer who went through
the process of shifting to a full-time remote role myself.
Freelancers have gone through many unique chal-
lenges themselves, and these challenges can either help
or harm their prospects as a member of your team. It’s
worth delving into the specifics of just what makes a
freelancer tick, and what will help them succeed as a
remote team member.
I was a freelancer for almost five years. And al-
though it was one of the best decisions I could have
made at such an early stage in my career, it wasn't easy.
95

Starting with only the networking I'd gained in college
and during the single year of an entry-level marketing
job at a nonprofit organization, I began consulting for
other NGOs, producing media, websites, fundraising
documentaries and other marketing materials. It was
extremely out-of-the-box: I traveled to 25 countries
while a freelancer, meeting people that would end up
being crucial to my career later on. The first year was by
far the hardest. I learned everything the hard way. I
wasn't picky enough at the beginning, and took every
job I could get, even if it didn't pay very much or I
didn't like the client very much.
Like most freelancers, it was a slow and grueling
start. But by the end of the year, I was making a couple
thousand bucks a month and was able to quit my
barista job. The grind slowly got better and better, even
though I didn't ever make a significant amount of
money freelancing. But it did let me have the freedom
to make decisions that I couldn't have made otherwise.
And it did provide direct hands-on experience on the
basics of operating a business, and all the soft skills in-
volved in that: interacting with clients, invoicing, re-
96

porting, banking, communication, and so on.
Like everything, there are some benefits and down-
sides to freelancing. And some of them I couldn't fully
appreciate until later, after I'd gone through a few years
of remote employment and (eventually) as a small busi-
ness owner. The most immediately impactful benefit
was ultimate freedom: I could do whatever I wanted,
whenever I wanted.
Financially, it wasn’t easy. But at the same time, it’s
hard to complain about. I made more than I spent, and
did almost anything in my spare time between gigs.
There were long weeks in which I did nothing except
lounge around, ride my motorcycle, fly to Costa Rica,
work on some hobbies, and hang out at coﬀeeshops.
Then, I would work 60 hours a week for months at a
time to make up for it. The downside was the income
instability. Even though I did technically make more
than I needed, it was still a pittance for a college grad in
America. I would shift between an $11,000 month, and
then a string of $400 months. It was both exhilarating
and exhausting, and in the end the stress that comes
from not knowing whether you’d have work next
97

month got to me. Even if it meant settling for a lower
income, taking a year to work a steady job was worth it
for the mental peace of mind.
It’s important to note that freelancing is an entirely
diﬀerent beast than actually owning a small business.
You’re not a small business owner: you’re a rogue em-
ployee for hire. Even though many of the principles are
the same, and many best practices carry over, there’s an
unavoidable stigma about being a freelancer. As a free-
lancer, you’re also not a consultant, which also seems to
be a terribly misused word. Consultants in the real
sense are tenured individuals who have successfully re-
tired from the corporate world and have insight that
saves the company more money than they cost to hire.
When you’re looking to bring a freelancer onto the
team in a full-time role, remember these aspects that
make up a freelancer’s life: independence, flexibility,
instability, and freedom. The first question to answer is:
why is this freelancer making the shift to full-time?
If the answer is “they need structure in order to be
successful”, they’re not going to be a great fit. Why?
Simply because remote work does not oﬀer a great
98

structure for folks who aren’t already self-directed.
Many freelancers fail out of freelancing because they
simply cannot structure their own work day. You’re not
going to be able to fix this without a strict structure
that crosses the line into micro-management.
Other freelancers quit freelancing because they
want a stable income. And this is probably the best rea-
son behind seeking out a full-time job: everyone needs
a stable income, and sometimes the existing path just
isn’t working the way you want it to. There’s no shame
in that, and I encourage managers to consider the need
for stable income a positive indicator for a potential job
candidate.
Other times, freelancers simply want to change ca-
reer paths. While probably not suitable for hiring into a
hyper-specific skilled role, for most entry-level or mid-
level positions this is also a great reason.
The other things to keep in mind are the factors
involved in being a successful freelancer.
First, they almost invariably had an unstable in-
come (unless they were smarter than me, and developed
ongoing retainer relationships with their clients).
99

Second, they are used to feast or famine and proba-
bly work accordingly. They will not fit easily into a role
that requires careful plodding work, day in, day out.
They will fit best into roles that require weeks of hard
work, then weeks of rest. In other words, project- or
event-based roles.
Third, they will want freedom and independence.
The entire reason they’re applying for a remote position,
and not a traditional oﬃce position, is because they
want the ability to structure their day and maintain a
semblance of control on their day-to-day life. Free-
lancers are excellent for self-directed, independent posi-
tions.
You’ll find that certain positions and verticals are
filled with potential freelance employees. Freelancing is
diﬃcult, but it’s the career of choice for more and more
mobile creatives and developers. Perhaps the most lu-
crative profession for a freelancer is software develop-
ment. If you’re going to trade your time for money
(which is essentially what freelancing is) then you might
as well make as much per hour as possible. Graphic de-
signers, video editors, copywriters, and other creative
100

types are also common careers that do well in freelanc-
ing.
On a different side of the equation than freelancers
are candidates who have already been working in re-
mote teams. Existing remote workers are a different is-
sue entirely. And it’s usually a non-issue, as they’re used
to working for someone on the other side of the world,
but you’ll need to be careful to adjust their expectations
for their new work home.
For example, I worked for an online airfare compa-
ny as a remote employee for almost two years, nominal-
ly as a creative director and head of special projects. The
projects I worked on involved content creation, video
production, affiliate marketing, branding redesigns,
SEO, and other web-based marketing skills. The posi-
tive aspects of the job meant that I didn't have to relo-
cate, had a steady paycheck, had some great peers, and a
healthy travel budget (I spent this on filming a 40-day,
18-flight trip around the world). The downsides were
limited future potential and limited benefits. My salary
was around the same as I made freelancing, but was still
a bit under market average. Anya worked remotely for
101

the same US-based company, first in paid search and
then as marketing director. She managed a small team
of marketing employees, ran PPC campaigns, oversaw
aﬃliate programs, and was in charge of analytics and
business intelligence. The positive aspects of the job
were much the same for her: a steady paycheck, ability
to work from home, some international travel, and
freedom to learn new skills. The downsides were simi-
lar: no career path upwards, and little outsized income
potential (that’s why we ended up founding
Discosloth!)
You may also come across former business owners
who are looking for a position in a remote company.
Owning a small business is my personal favorite way to
work remotely, but it doesn’t necessarily mean that it’s
the greatest place for a candidate to come from.
Not everyone is cut out to run their own business
or working for themselves, and that’s fine. But owning a
business - having the responsibility of employees, liabil-
ities, vendors, and overhead - is a step beyond freelanc-
ing.
A successful business owner creates a company that
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begins to take on a sort of personality beyond their
own, and the momentum behind this is what separates
that dude armed with a fully-stickered MacBook Pro at
a coworking space from a real business.
Transitioning a former business owner into a re-
mote team, however, is one of the absolute trickiest
things you could do. Although I have the highest
amount of respect for small business, I can’t imagine a
situation where I’d be able to smoothly integrate a for-
mer business owner into Discosloth. The mindset of
responsibility and control is drastically different, and
you’ll need to ensure that there won’t be conflicting
management styles.
If you’re looking for papers or diplomas that make
someone qualified for remote work, you’re wading in
the wrong creek. There aren’t any.
The ability to have a successful and lucrative career
without ever stepping into the office wasn’t in existence
when most of us went to college. Even today, the nor-
mal progression from college graduate to career success
usually involves an office job, not going remotely right
off the bat. It’s rare that someone doesn’t have to pay
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their dues to the man, by going into the office for the
first few years of their career to do the entry-level stuff
that lets them work their way up the ladder.
There isn’t a single specific certification that makes
someone a good fit for remote work. There isn’t even a
specific experience or job function that ensures that
someone will work out. It’s more about personality than
anything else. And chances are, you’re going to get job
candidates that veer towards the slightly weird.
After all, these are people who want to work from
abroad, or work from home. That’s still very unusual.
But it’s also a good thing.
If you’re looking for qualifications to find in hiring
employees for a role in remote work, there isn’t a certifi-
cate to earn, a course to complete, or a major to declare.
Remote work happens when you’re highly driven,
independent, self-directed, and able to structure your
work life without the constraints of an office building.
Employers who are hiring a remote employee are
looking for characteristics that are, in general, a bit ab-
stract and undefined. They’re looking for people who
love to travel. They’re looking for people who are good
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at writing. They’re looking for good communicators.
They’re looking for go-getters. They’re looking for peo-
ple who are tech-savvy.
In short, they’re looking for folks who are at the top
of their game. They want people who have had flexible
roles with a large amount of responsibility.
The path to gaining these characteristics isn’t at-
tained through a degree. It is acquired through experi-
ence, and that’s something that only those individuals
can create for themselves.
105

The Blueprint For Going Remote
107

One-Size-Fits-All?
Every company is diﬀerent, and there is no one-
size-fits-all solution for implementing the perfect re-
mote work structure.
There will always be outliers. Perhaps on one hand,
we’re talking about a tiny company of two people who
are highly driven and ambitious. They don't need any
structure at all, they just seem to get things done. On
the other hand, it's a Fortune 500 company who's con-
sidering shifting an entire department of 1,000+ people
into remote roles. It's very diﬃcult (and dare I say,
disingenuous) to give solid, qualified advice to either of
these entities without knowing more about their intri-
109

cacies and idiosyncrasies.
That said, there are always many more entities in
the middle of the bell curve. For every global multina-
tional company going remote, there are hundreds of
mid-size companies who perhaps just employ a few
dozen workers. And if you fall in the middle of the bell
curve, whether you're located in New York City or Ma-
laysia, whether you have five employees or fifty employ-
ees, chances are that you've got more similarities than
diﬀerences.
This section is intended to encapsulate our recom-
mendations for remote work structure into a simple
blueprint, meant for the vast majority of small to medi-
um businesses. It's likely not terribly relevant for either
the solo freelancer or the massive corporate behemoth -
but this makes it even more accurate for the rest of us,
those who own small companies with just a few em-
ployees scattered around the globe.
First, we'll underline the importance of onboarding.
When you're hiring talent into your company, it's im-
portant to immediately introduce people to your meth-
ods and expectations when it comes to working remote-
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ly. This will include training documents, contact lists so
they have easy access to colleagues, recommended meet-
ing frequency and structures, how to organize HR
needs like vacation scheduling, and how to shift to an
emphasis on business goals, rather than screen time.
Then, we'll talk about communication. In other
areas in this book, we talk about communication in a
very broad and holistic way, but in this section we'll try
to dig deep into the practical aspects of actually putting
it into practice. This will include how to triage com-
munication channels, meeting frequency and length,
software tools to implement in order to improve your
communication, and project management.
And finally, we'll talk about motivation. This is a
big deal in the world of remote work, since the distance
(both physical and mental) can often de-prioritize or
discourage productivity. Things we'll go over in our
motivation section are financial (bonuses based on per-
formance, profit sharing, referral bonuses) and educa-
tional (paying for conferences, in-person retreats, and
coworking subsidies).
A blueprint is never truly one-size-fits-all, but I
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think that you can extract a bit of universal wisdom
from it all the same.
Treat it as a springboard, and adjust to your specific
industry’s needs, history, and quirks.
112

Team Introductions & Onboarding
Start strong. Introducing incoming team members
to your company's culture, methods, and expectations
of working remotely is one of the most important
things you can do. And, if you’ve got many existing
employees who are about to go remote, it’s equally im-
portant that they are given all the information necessary
to make the upcoming adjustment to their work life.
It’s something that requires a little bit of careful thought
and investment up front, but saves you myriad prob-
lems and troubles down the road.
A solid onboarding process is something you need
to have in place anyway, at any company, but it's espe-
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cially important in a remote company since everything
is still unfamiliar territory. When you start implement-
ing a remote policy for your company, you will sudden-
ly realize how many behaviors and policies are just tak-
en for granted.
In a traditional office, decades of experience and
tradition have instilled some basic expectations in both
workers and their managers. We all know (or should
know) the basic traditional office etiquette - don't take
the last donut, refill the water cooler, don't be late to
work, answer the phone politely, don't clip your nails at
your desk, don't blast your music out loud. But how
does this basic office etiquette translate into the remote
world?
It ultimately comes down to the golden rule: treat
others as you would be treated. Practically, though, how
remote golden rules play out are entirely different than
the golden rules of the cubicle.
There isn't a last donut to take - those donuts are all
yours. Clip your nails at your desk all you want - you’re
the person having to clean them up, anyway. Blast your
music as loud as you want - only your cat can hear it.
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Don't worry about showing up at eight o'clock on the
dot - your teammate won't be awake for another three
hours anyway. Instead, the etiquette transforms into
respect for other, as well as their time. Get your work
done, communicate well, don't intrude, keep files orga-
nized, look presentable on camera.
One of the best ways we have found to introduce
new employees to your remote work is by creating a
training guide - an introductory course, so to speak -
for your company. Many companies already have an
employee handbook detailing policies like vacation
time or how to answer the phone, so this is merely an
extension of a handbook, with a lot more information
thrown in about how remote work is expected to be
accomplished in your company.
For remote work, we have found that this docu-
ment usually looks like an outline of the company
structure itself. It details how things are done. Ques-
tions that you should answer in this document: How
do I schedule vacation? Who is in charge of this? How
should I communicate? How often is my performance
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reviewed? Can I date my coworkers? When do I get my
annual bonus? To whom do I report?
Not only should this document detail the company
structure, but it should also detail some basic house-
keeping. Other subjects it should address: what soft-
ware should I use for videoconferencing? Where do we
keep passwords? What VPNs should we use? What are
our security protocols?
For companies with a head count of over 5-10 em-
ployees, a company-wide contact list is essential. Create
a spreadsheet of people in the company along with their
roles, so it’s easy for your new employee to know who
to contact when they have some specific questions.
Additionally, the larger the company the more de-
tailed this spreadsheet needs to be. Consider adding a
matrix with each member's skills and specialties, so that
when one employee wants to know about sending out a
client update, they know who specializes in email mar-
keting campaigns, or if when another employee wants
to know about pricing margins, they know who is in
charge of procurement.
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Part of the struggle (and possibly benefit) is that
remote organizations develop a flatter hierarchy by na-
ture. There aren’t as many places for middle managers
to insert themselves, so things tend to get done a bit
more eﬃciently. This means colleagues, who are already
all separated by distance, can more easily reach out di-
rectly to who they need.
One of the problems with this is that certain em-
ployees can befuddle the process and bog down other
employees with meaningless work. One of the benefits,
if harnessed correctly, is that a flatter hierarchy speeds
things up and removes dead weight from the equation.
This is entirely up to your organization, however, and
depends upon the amount of teams and departments in
your company.
In general, we don't recommend too many meet-
ings to maintain productive remote work. At the very
least, meetings are something that should be minimized
rather than maximized. The sole exception is during the
first couple weeks of an employee's tenure at your com-
pany, and we recommend daily meetings at a mini-
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mum.
The purpose of these meetings is to familiarize the
employee with the company's culture and structure,
and above all to introduce them to others within the
company. Fostering personal relationships and familiar-
ity with others is vital to the long-term health of both
the company and the employee. During these introduc-
tory meetings, it's good to bring in as many colleagues
as possible.
As a manager, there are multiple reasons why this is
so important. First, you get to see directly how your
new employee works within your organization. Second,
you can ensure that they are getting all the information
(both from a practical standpoint and a cultural stand-
point) that is critical to their ongoing success in their
role. And third, you can immediately identify any po-
tential future problems - especially interpersonal fric-
tion that might pop up between this person and others
within the company.
We usually recommended having daily meetings for
the first two to four weeks, adjustable according to the
role and the employee's ability to adapt. Make sure to
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leave room at the end of every meeting for the employ-
ee to ask questions and receive feedback on points that
pique their curiosity. The meetings should be informal
and not too long, perhaps thirty minutes to one hour at
most.
During the course of hiring, and then immediately
following the employee's first day, it's crucial to set the
appropriate expectations.
These expectations can't be the same expectations a
company would have for employees that come into a
traditional oﬃce every morning. And that's actually a
critical diﬀerentiator that both the employee and you,
as a manager, have to embrace.
Right now, remote work is still a relatively uncom-
mon feature for a company. Getting a good job that is
totally remote is still competitive and fairly rare. Be-
cause of this, companies have high standards for what
they expect from an employee, and employees have
high standards for what they expect from a company.
In order to do well in a remote role, a person needs
to be extremely well motivated, have a doggedly hard
119

work ethic, and have an outsized amount of personal
independence and creativity. If someone lacks these at-
tributes, it's hard enough to manage them in a tradi-
tional setting, much less a remote one. Someone who
needs constant hand-holding is not going to thrive in a
remote role.
At the same time, you cannot hire an excellent re-
mote employee and expect to treat them just like any
other person. You will likely need to give them a signifi-
cant amount of independence - letting them set their
own hours and giving them a wide rein on their
projects and responsibilities. In all likelihood, this em-
ployee did not choose a remote role to get a huge pay
bump or a career boost (these are both things that re-
mote work doesn't exactly have a great reputation for at
the moment). They likely chose to pursue a remote role
in order to have greater personal independence and a
flexible work environment, and to be surrounded by a
progressive culture and, probably, work on unusual or
innovative projects. In response to this, it's important
to identify why an employee is going remote, and cater
to those needs.
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Setting goals should be about deliverables and re-
sults, not about how many hours they put in staring at
the screen. The whole reason you're switching to re-
mote work, after all, is because the traditional method
of work is broken in many aspects.
When we started Discosloth, both Anya and I had
years of experience working in other companies, both
remote and traditional, and we were adamant of a few
things we'd never do in our new startup. One of those
was tracking employee hours. Granted, we operate in a
technical field that attracts driven and tech-savvy indi-
viduals, so we have the luxury of being in good compa-
ny by default. From a full-time employee, we do not
expect forty hours of work a week. That is irrelevant.
We simply expect results that correlate with a full-time
employee. If it takes them two hours a week to deliver
amazing results, that’s beautiful. If it takes them eighty
hours a week to deliver those same results, that's just
fine as well. The results are what we're looking for, not
the time in which someone's butt has warmed a chair.
This approach is nontraditional and makes many
more conservative companies squirm a bit, but it's the
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approach that makes the most sense from a remote
company. We've seen the absolute opposite approach
being taken, and it seems disastrous: companies that
install screen monitoring apps on their employee's
computers, require employees to clock in and clock out,
or even put performance-measuring quotas on things
like the number of Slack messages sent, emails replied
to, or documents created. I can't think of anything
more destructive to your company's culture, and ulti-
mately your company's productivity. No self-respecting,
ambitious employee will stick with your remote com-
pany if you treat them like a factory assembly line.
In the same vein, it's good to be clear about how
you parse and analyze performance. Detail very clearly
how often you will review their performance, and how
you calculate that performance. This doesn't mean you
have to directly tie 100% of their compensation to their
performance, or that you really need a numerical score
associated with how well they're doing (after all, very
few roles can be quantitatively assessed like this). It just
means that you need to have direct, results-focused dis-
cussions on a regular basis, and communicate how this
122

aﬀects their job as a whole.
123

Finding Remote Candidates
So your company is going remote.
Ideally, you’ll be transitioning existing employees
into remote roles, but eventually you will want to hire
from outside the company.
This is one of the trickiest problems you will run
into, and you’re now competing with a world of VC-
funded tech companies, New York City and San Fran-
cisco-based startups oﬀering stratospheric salaries, and
some of the most adaptable and tech-savvy candidates
ever spawned on this earth.
There are a few ways you’ll be able to start getting
applications in your inbox, and these primarily involve
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remote job boards, traditional job postings, and your
existing network.
Your existing network is by far the highest quality
method of finding a good employee, but it depends
greatly upon just how professionally established your
company and your current employees are. If you’ve got
a few team members and a solid work history, it won’t
be hard to start getting the word out.
Referrals from within your company are an auto-
matic filter that almost certainly ensure the candidates
will be a good fit with your company’s culture. Team
members typically recommend people they would be
comfortable working with, and in order to avoid em-
barrassment they’ll usually refrain from recommending
people with drastic problems. Having a job referral in-
centive program can help encourage your team mem-
bers to recommend quality candidates: we’ve seen com-
panies oﬀer anything from $500 to $5000 to employees
that recommend a candidate who ends up getting
hired.
Remote job boards are extremely popular, and gen-
erally provide you with fairly relevant applicants. We’ve
125

used remote job boards when hiring for Discosloth, and
saw the most technically relevant applicants from these
channels. However, the downside is that posting can be
expensive (usually around $300 per listing) and are real-
ly only good for technical roles like software developers.
Traditional job posting boards are cheaper, and
much more high volume. The quality of applicants
from channels like Indeed or Monster are questionable
at best, especially if you are hiring for a role that re-
quires specific skills or experience. The cost is free to
slim, but you will soon be engulfed with a never-ending
deluge of applicants from every place imaginable in the
world.
When Discosloth hired our first employee, we
thought, at first, it would be easy to find who we need-
ed. We have the entire world at our disposal, right? It
turns out, it was harder rather than easier. We were now
competing with companies across the world for a very
specific skillset. We tried all of the channels we could
think of: specialized remote job boards, traditional job
postings, and inquiries within our network.
Remote job boards didn’t give us many applicants
126

we were satisfied with. We were looking for an entry-
level Google Ads specialist, which doesn’t sound like
too diﬃcult of a role to fill. And it’s a tech-focused
marketing role, which is perfect for remote work. The
variety of applicants, however, was wildly confusing. I
had an application from a fellow in California who
made his salary demand up front in his cover letter. I
appreciated his initiative, but he demanded $182,000 a
year for a clearly entry-level job, so we took a hard pass
on that one. I had a slew of applicants who seemed like
potentially good cultural fits, but the majority didn’t
have the specific skills we were looking for.
Traditional job postings were quite the experience.
We posted the job on Indeed, and within a week had
over 300 applicants. And then the job posting got syn-
dicated, so more and more sites picked it up. That was a
few years ago, and we’re still getting applicants for that
original position to this day. The problem was that, out
of all of these hundreds of applicants perhaps five or ten
were actually relevant. We looked at a resume of a
pharmacist in Hawaii, a grocery store cashier in Ohio,
an insurance salesman in Kansas, and everyone else
127

from interior designers, telemarketers, professors, and
landscapers.
In the end, after weeks of searching fruitlessly, I de-
cided I’d need to hire manually. Oﬀ to LinkedIn I went,
and painstakingly searched for applicants who were as
close to what we wanted as possible. I narrowed down
the entire world to around forty potential candidates,
and sent each of them a personal message. Out of all
forty, only five responded. Three were not interested,
one was actively looking for a job, and one already had
a job but might be interested.
The first candidate, who was looking for a job, cor-
responded with us a bit and then showed up to our first
virtual interview, just to announce she’d already accept-
ed another job (thanks for your time, an email would
have worked). I think she was looking for an oﬀer to
negotiate with her other job, but I didn’t feel like in-
dulging her. The next candidate was the perfect fit, and
we entered into negotiations which eventually con-
vinced her to leave her current job and move to Dis-
cosloth.
That’s the process of hiring that we first experi-
128

enced, and it hasn’t changed much for most smaller re-
mote companies since then. Of course new companies
like us have to be pickier about hires, as salaries are the
most significant part of our capital expenditure. Expect
to spend weeks, if not months, on finding the appro-
priate candidate, especially if you’re hiring for a crucial
or technical role.
129

Communication Tools & Standards
Having a clear and defined communication struc-
ture is essential to the health of a remote company. I'd
say that, actually, it trumps almost everything else when
it comes to making or breaking the success rate of going
remote.
We'll cover the details of how we triage communi-
cations in a dedicated chapter, but the basics are fairly
straightforward to adopt.
The first thing to realize and acknowledge is that
everyone has diﬀerent communication styles, and there-
fore everyone in a team has to learn to compromise
their desired style and integrate into a common stan-
130

dard, for the sake of cohesiveness and basic teamwork.
It is never easy to gain total adoption of a communica-
tion structure, but it's essential in order to retain any
semblance of organization and productivity.
Unless your team members have an unprecedented
level of familiarity and common communication pref-
erences, you'll need to gently force adoption of your
established communication protocol. We triage com-
munications through three channels: chat, email, and
meetings. Chat is for immediate needs and questions
that need a response within the hour, but aren't crucial
enough to bankrupt the company or lose a sale. Email
is for questions that need a response within 1-2 days
and probably deserve a longer, in-depth response of sev-
eral paragraphs (this can be bigger plans, scheduling
events, discussing strategies, or anything that probably
needs persistent documentation). Calling a meeting
should be one of the rarest things that ever happens in a
remote company. Meetings are for things that need an
answer now. Meetings (whether a phone call or a
videochat) that aren't regularly scheduled are for dam-
age control or in-depth brainstorming for an immediate
131

issue.
We suggest getting your entire team used to this
process of triaging their communication. The tools in-
volved don't really matter so much as the way you use
them: chat is chat, whether it's Slack, Google chat, or
old-fashioned SMS. There will always be folks who pre-
fer one form of communication over another: perhaps
it's a software engineer who prefers Slack over email, or
perhaps it's the sales guys who are always on the phone
and sending email but never use chat. The key is to
blend everyone together into a consistency that ensures
everyone who needs the right information has access to
it when they need it - even if it means picking up the
phone, when you hate talking on the phone.
Here's why triaging works best, in our experience in
various companies. Instead of having constant meet-
ings, it’s easier and faster just to chat through your pre-
ferred method if you have a small question, or if you
want to check in on something. It's best to use chat
within normal working hours for the recipient (no em-
ployee wants to get an accidental loud notification on
their phone at 4am). Chat should typically be used in
132

situations where the recipient can respond either in live
time, or within an hour or so.
For questions that need careful responses, or tasks
with more details, or when the recipient is asleep, use
email. It's long been an assumption in the corporate
world that important business emails should be re-
sponded to within a day, and we feel like this is an ap-
propriate timeframe. Even if it's not a full answer, a
good policy is to have colleagues reply with a "got this,
will respond in more details later" sort of response to let
the sender know that the message is on their radar. It's
important, however, to not abuse email. Sending
dozens of emails just clogs up inboxes and is diﬃcult
for the recipient to wade through, so reserve it for im-
portant issues and discussions that need time to think
about, reflect, and respond to with carefully thought-
out paragraphs. Email isn't chat. It's a letter, and as
such is best avoided when the subject is super urgent.
For meetings, when you've got an urgent issue at
hand it is often best to have a video conference with the
other parties. As remote work doesn’t allow for the same
interpersonal connections that a traditional oﬃce does,
133

video is very important to keep it as personal as possi-
ble. Most video conferencing tools allow you to share
screens, which is very helpful in a technical setting
when you have an issue that you cannot easily explain
in words.
Of course, video conferencing doesn't always work
if someone is on the road or if you aren't in a setting
that is conducive to video: driving, in an airport, or a
coﬀeeshop, for example. It's usually not very courteous
to hold a video chat in a coﬀeeshop, so in this case you
should easily be able to pick up the phone and step out-
side for an important talk. Often decisions can be made
much more quickly when you simply pick up the
phone or turn on Zoom and work through something
face-to-face.
Our rule of thumb for meetings: less is more.
If you can structure your company so that you nev-
er have to endure a single meeting, you've hit the
motherlode. Unfortunately, this is hardly possible or
realistic, so the goal should be to reduce the amount of
unproductive dead time (also known as meetings) as
134

humanly possible.
When you're dealing with a remote team, the rules
change. In the office, it's easier to schedule meetings.
Just pick a time between nine to five, and that's the
time in which everyone will be available. In remote
work, especially across different time zones, this is no
longer applicable.
It's important to remember that not everyone likes
working early mornings or nights. And since you've
established remote work as an official policy, it doesn't
really make sense to require all work to be done on a
single time zone's schedule - that sort of kills the entire
purpose of asynchronous, distributed work, doesn't it?
It's unreasonable to expect your employees on the
other side of the world to keep the same daylight hours
as you do, so a significant amount of time flexibility is
needed. It's not unreasonable, however, to require at
least two hours of overlap. This is a common tactic in
remote teams with members on all sides of the world,
because it's usually fairly easy to accomplish: early
morning on the Pacific Coast will be mid-day on the
East Coast, and early evening in Europe.
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The other hidden benefit of requiring only a couple
hours of overlap is that it forces a limited amount of
meetings. It time-boxes everything, and that's usually a
good thing when it comes to video conferencing or
phone calls.
Depending on where you're coming from the cor-
porate world, you've likely had regularly scheduled
meetings at various frequencies: daily, weekly, monthly,
quarterly. This doesn't work the same in the remote
world.
Although you might end up having daily meetings
in your company, they shouldn't be expected or sched-
uled. After all, a meeting doesn't just last thirty min-
utes. It starts a few minutes before the scheduled meet-
ing, as people prepare and wind down everything else
they're working on, it lasts for the thirty minutes
scheduled in the calendar, and then it lasts for a few
minutes afterwards while people get back in their flow
and pick up whatever they dropped to attend the meet-
ing.
We don't recommend regularly scheduled daily
meetings, and if they end up being necessary after all,
136

keep them very short and don't use them for micro-
management. They should be at most fifteen minutes
long, and focus on the team's connections and under-
standing where everybody else is at on a holistic level -
not in dictating every step of the day.
When you're first onboarding a new employee, dai-
ly meetings are probably necessary, but as soon as
they're settled in, give them breathing room to start
orchestrating their own work days and being responsi-
ble on their own time. The first month or so should be
used for training, and helping set expectations and goals
for the new employee.
Weekly meetings are perhaps the best option for
ongoing, regularly scheduled meetings. We found that a
one-hour Monday morning meeting, with the purpose
of discussing big-picture ideas and current problems,
and a time for the manager to coach the employee in
diﬃcult areas, is usually the best approach.
Depending on the size of the team and the breadth
of your company's projects, a monthly or quarterly
meeting may be useful. In this case, discussing new big
projects, or overarching company goals, is important.
137

It's also the perfect time to get employees in diﬀerent
departments, who may not otherwise interact, to see
what others in the organization are working on.
Of course, performance reviews should almost al-
ways be performed on a regular basis, and these are al-
ways best done in a video format.
You'll always have urgent issues pop up that need a
meeting called. Sometimes things may need rapid, in-
stant discussion. These are unavoidable and crucial, es-
pecially in the event of a big project or unforeseen is-
sues. Keep your meetings time-boxed, don't feel afraid
to redirect the conversation if it starts to wander, and
make sure to respect the time of all those involved.
It's good to codify meeting etiquette in some man-
ner - and this should revolve around respecting the time
of others. If someone doesn't need to be in a meeting,
others shouldn't require them to be in it. If someone
wants to leave a meeting, they should be able to when-
ever they want. We've seen some colleagues go invite-
happy on meeting times, clicking down the contact list
until half of the company is scheduled to show up to
chat about something unimportant. Don't do this - and
138

don't encourage your employees to do it, either.
139

Motivation & Performance
We've all had those days when you just don't want
to get out of bed. Everyone needs motivation - but
you’ll need it even more when working from home.
The brilliant Nassim Nicholas Taleb once said, in
his book Skin In The Game, that “what matters isn’t
what a person has or doesn’t have; it is what he or she is
afraid of losing.” In short, give every one of your remote
team members an excellent experience working in your
company, and the performance will be forthcoming.
Creating opportunities for your employees to be
comfortable, and to be able to continue improving
themselves, is crucial to a sustainable and productive
140

remote policy. While working remotely is generally ex-
tremely productive, things can easily fall through the
cracks, and a few small steps can go a long ways in
making your team feel more comfortable working hard
towards their goals.
We have found that some of the most important
motivational policies directly address a few glaring chal-
lenges of remote work. Namely? The social aspects, the
financial aspects, and the career aspects. If remote work
has any downsides, it's that it can be personally isolat-
ing, pay less than the equivalent traditional roles, and
potentially harm a worker's long-term career aspects
because of less networking and growth abilities. Any
policy that attempts to counteract these will be wel-
comed into an organization!
To address the social aspects of remote work, there’s
a plethora of available options. One of the first things
we instituted at Discosloth, when we started hiring for
remote roles, was a coworking/coﬀeeshop stipend. This
covers either a membership at a local coworking space,
or the purchase of a few drinks at a local coﬀeeshop
each day - to be used at the employee's discretion.
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We also encourage attendance at industry confer-
ences. We think that this is an important part both in
ongoing training (who doesn't want your employees
familiar with the latest industry trends?) and also in
creating a networking opportunity for them. Sponsor-
ing attendance for even a single conference per year is a
great motivational perk.
Other policies we've seen remote companies insti-
tute include free books (for example, purchasing up to
$50 of books a month for an employee to read). I'm
particularly fond of this one, as it's a low-cost but en-
gaging policy which will also show managers the books
their employees are interested in - and perhaps where
their skills and interests of growth lie.
We also think that face-to-face meetings between all
members of your team is crucial: and, if possible, this
should happen at least once a year. This is one of the
first ideas that remote companies throw out the door,
because it's expensive to put a butt in an airplane seat.
But keeping your interaction totally remote is short-
sighted, in our opinion. As much as video conferencing
enables us to work remotely, it's still a sub-par form of
142

communication. Real bonds are created when you're at
a table sitting across from a real-life, flesh-and-blood
colleague. A team that's eaten a great meal and gotten
tipsy together will do a lot more for each other, and feel
better about the company’s work as well.
But it's not just about social and career aspects - it's
also about the financial aspects.
It pains most corporate spreadsheet warriors to hear
it, but your team isn't working with you because they
love you. Or because they believe in your mission. Or
because they want to change the world.
Your team is working with you because they need an
income. As altruistic and well-meaning as your company
and colleagues may be, the world isn't a charity. Mak-
ing rent, paying bills, and saving for retirement is more
important for your employees rather than just the privi-
lege of being part of your team.
That's why it's important to recognize and encour-
age this. You're employing unorthodox, outside-the-box
remote workers, and chances are they're among the
most ambitious and well-performing individuals in
their field. Not just anyone can compete for a remote
143

position, so they deserve to be rewarded for their exper-
tise. If you provide everything else, but forget to reward
them handsomely with cash, you're going to see an in-
sane amount of churn.
Many companies use a recognition and reward sys-
tem. This is a great idea, but it can't be divorced totally
from financial reward. Although it's nice to be "em-
ployee of the quarter", it doesn't mean much to your
employees once they've lost that brief flash of
dopamine. Having some form of financial reward at-
tached, even if it's a small amount, means infinitely
more than a fancy title.
We encourage a holiday bonus system. Our team is
scattered across the United States and Europe, so we
provide an annual bonus around Christmas. The
amount changes according to performance and how
well the company has done that year, but the amount
can be anywhere from a small gift to a full "13th
salary,” a popular form of bonus in Europe which is an
extra month's salary given at the end of the year.
Profit sharing is another popular incentive. I love
the idea of profit sharing. In practice I haven't seen it
144

implemented very well. Like most numbers, the math-
ematical gymnastics involved in calculating profit shar-
ing can be a little devious. If you do decide to imple-
ment profit sharing with your company, it's important
to be very transparent and open about how this is calcu-
lated. It's not a suitable option for all companies, but if
it is suitable for yours, make sure all your company
profit numbers are totally transparent so that you en-
courage trust within your team.
I’ve seen (and experienced) profit sharing which is
little more than a glorified pat on the back. The idea
sounds nice, but then the company has an extra prof-
itable year and needs to pay out more than expected to
the employees. The next year's profit sharing calcula-
tions tend to be adjusted down accordingly.
Bonuses calculated on personal performance are
excellent incentives, and we're a fan of these in our own
company. Referral bonuses are popular since it is easier
to hire a new team member based upon recommenda-
tion rather than an applicant coming from who-knows-
where. This can save weeks or months of time, and
gives you a much higher chance of being compatible
145

with the new team member.
For small teams or point persons on special
projects, developing project bonuses can be an incentive
to get specific things done quickly and efficiently. These
one-off bonuses can be varied: for example, it could
look like “get 300 new leads by February and we will
pay out a $4,000 bonus” or it could look like “cut
down email response time by 2 hours in Q3 for a $250
bonus to everyone on the team.” The end goal, however
structured, should be the same: help the colleagues in
your company have skin in the game. Reward for effort
is always a great thing for your company’s long-term
health.
146

Making It As A Remote Worker
147

The Importance Of Structure
If you've spent more than a few weeks working
from home, you've heard multiple people making jokes
about how much you are actually working.
What people think is irrelevant, of course, but it
does point to a common problem with remote work
that I've seen dozens, if not hundreds, of people strug-
gle with.
When I worked at a regular nine-to-five office job,
things were entirely different. It was highly structured.
Everyone showed up to work around the same time,
everyone ate lunch at around the same time, and every-
one left the office around the same time. Because of this
149

structure, traditional work does make it easy to settle
into a predictable and comfortable work schedule.
I've been working remotely since 2011. Before that?
I was waking up at 8, showering, driving 15 minutes to
work, sitting in a fancy open plan office, grabbing cof-
fee from the break room, going out for lunch, working
until five, and heading home for dinner and a few
episodes of Buffy the Vampire Slayer before dozing off to
replicate the previous day's structure once more,
groundhog style. The only variations in my daily
schedule were periodic work trips, a few days in New
York or Seattle, before heading straight back to the
grind.
Overnight I went from this strict weekday schedule
to freelancing. I had freelanced on the side previously,
so the difference in the work itself wasn't challenging,
but being a young adult without a normal job was a
strange role to explore. At that time, there weren't really
such things as coworking spaces peppered throughout
every city. Most freelancers or consultants were older
than I, and had stable careers which meant they proba-
bly worked from their own office rented out somewhere
150

downtown. I was stepping into a brave new world, and
the first few years were tough to deal with.
The first months were the biggest adjustment. As a
freelancer, I didn't have that many pressing meetings or
deadlines, so my bedtime got later, my breakfasts be-
came brunches, and I did what most 22-year-olds do,
which is drink a lot of beer at evening and drink even
more coﬀee the next morning. I didn't have much life
purpose at the time: as long as I could make rent, I con-
sidered myself doing alright. There wasn't much moti-
vation to go the extra mile. This first few months of
total freedom was enough to turn me into a potato. Af-
ter this long summer of waking up at ten or eleven in
the morning, staying up until three in the morning,
and a lot of Pabst Blue Ribbon, I realized I needed to
implement structure if I was going to do anything with
my life.
I self-imposed a rigid schedule, and over the next
few months things got progressively better. I began
waking up at seven, showering, eating, and going to a
coﬀeeshop to work on a very specific and tightly held
schedule. I still left plenty of time for social activities (I
151

was twenty-two, after all) but forcing an early rise was
crucial to starting the day oﬀ right.
Now, before I go too far down this path, I'll have to
say that I don't think the same schedule is right for
everyone. I hear far too many guru hustler types talking
about how they wake up at four, go to the gym, lift 500
pounds, start work by six, and make twelve sales calls
by noon. These people are full of shit, so you may feel
free to ignore them.
Not everyone wants to wake up at four. Or seven.
Or even nine. Not everyone needs to go to the gym. You
can do whatever you want to - but you probably do
need structure.
How that structure looks like is dependent upon
you, your culture, your company, your surroundings,
your time zone, your career, and about one hundred
other factors in your life. I can't design a perfect life for
you, and neither can anyone else but yourself. The
schedule itself is beside the point - because the impor-
tant part is the structure, not what or when you're do-
ing it.
The traditional corporate work structure has many
152

downsides, not the least of which I think is a crippling
ineﬃciency and an emphasis on quantity of work rather
than quality, but there is a reason it is such a universal
constant. Humans have an innate need for structure,
and the enforced rigidity of a traditional work schedule
creates that structure for many people who couldn't
otherwise be bothered to do it for themselves.
That's why I think I need to reiterate something
I've alluded to very often in this book: remote work
isn't something that will work for just anyone. It works
for self-directed, ambitious, disciplined people. Usually,
these are people who would thrive or even exceed ex-
pectations at a normal job, so this self-direction and
ambition serves them well if they decide to transition to
a work-from-home or self-employed role.
One of the important things to consider about your
schedule is that it shouldn't just include work items. It
also needs to include play items. One of the hardest
parts about working remotely is the huge social change
that comes with it. You don't meet people very easily if
you're holed up in your home oﬃce all the time (and
video chatting with coworkers doesn't exactly count).
153

So you've got to make sure to force yourself to get out
of the house and head somewhere to have normal, face
to face, human interaction. For me, that included
working from a coﬀeeshop where I could interact with
the baristas and other regulars on a daily basis. It also
included heading to the local dive bar on the weekends,
where I'd meet up with buddies and listen to some
blues music. Whatever your jam is, it's important to
schedule some real-life humanity in there along with
the work, because you'll otherwise sink deep into a hole
of anti-social caveman life. I've been there, done that!
154

Working Remotely As A Freelancer
My first job out of college was in a trendy nonprofit
on the East Coast, and we had the open office plan,
single-origin coffee in the break room, and just about
everything except fat salaries. Yet at the core, it was a
much more traditionally-structured job than it ap-
peared to be at first glance. Senior management re-
quested their own offices (understandably) since they
preferred to have telephone conversations in private and
work in peace and quiet. We all showed up at 9 in the
morning and left at 5 in the evening. We drove back
home to eat dinner. It was quite normal.
It wasn't until a bit later that I started working re-
155

motely. After I left the trendy nonprofit job, I started
freelancing. Of course, this was over a decade ago, and
even in 2011 fully remote work wasn't really popular
yet. Even though I worked from home or coﬀeeshops,
the majority of my clients were still located nearby. I
still had to hop on a flight from time to time and travel
to an organization's headquarters or field oﬃce in order
to pick up a project, but this was rare. Increasingly,
though, I started gaining clients from further away,
without actually meeting any key decision makers in
person, and eventually a large part of my workload was
entirely over the internet.
I freelanced for five years, from 2011 to 2016. Even
in those five years, it was pretty impressive how the
technology changed to enable remote work. In 2011,
internet speeds were slower and less reliable, digital
payments weren't very sophisticated, there weren't
many solid places to work from, and working remotely
wasn't accepted as easily as it is now.
Internet speeds were acceptable, of course, just not
amazing. Even just a few years ago, unless you were lo-
cated in a large city, it was impossible to work with files
156

over a few gigabytes in size (I did a lot of media produc-
tion at the time, so large files were a big part of my
work life). It would take hours to upload a rendered
proof file. And given the fact that I often worked from
places in Africa or Central America or Asia, I'd often
leave my laptop overnight trying to upload a few hun-
dred raw photos, only to wake up in the morning and
find that the connection had died halfway through the
night. Now, it seems like internet speeds are much
more ubiquitously stable. Mobile internet, especially in
developing countries, has grown leaps and bounds be-
yond what it was.
Digital payments were painful, almost nonexistent.
For the first few years, I don't think I received a single
digital payment. It was all checks. This is not really be-
cause the tech wasn't there (PayPal and ACH transfers
were around, after all) but because large companies and
nonprofit organizations were still beholden to 1990s-
era payment structures, and they wouldn't use PayPal
even if they had an account. It wasn't until ridiculously
recently that accepting online credit card or ACH pay-
ments were made easier for freelancers or small busi-
157

nesses, with services like Wave or Stripe.
Working remotely was almost solely a work-from-
home-office and work-from-coffeeshop thing. There
were no such things as coworking spaces, so it was Star-
bucks or your local third-wave coffeeshop. And most of
the time, although you did tend to hobnob around
with other remote workers, it felt a little bit like you
were just that unemployed guy who hung out at the
coffeeshop all day. Near the end of my freelance career,
coworking started to become a bit of a trend. In the
smaller city I was located in at the time, a single
coworking space opened up, called the Hive. I went
over to check it out. It was immensely depressing - ba-
sically a few folding tables stuffed into an old-school
advertising company's dark back room, complete with
old carpeting and musty ceiling tiles. Now, of course,
coworking is a much bigger deal, but it's still not even
where it could be. It's currently in a bubble of ridicu-
lous proportions, with companies trying to rent a desk
for $700 a month. Call me stingy, but $700 would buy
me nine lattes per day at my local coffeeshop or an en-
tire office of my own. At some point, I think the bub-
158

ble, much like open office plans, will level out into a
more moderate playing field.
The stereotype of the unemployed freelancer is still
there, a little bit, but during my five years as a free-
lancer, people really didn’t get it. Not having an office
was equated with “unemployed” in most people's
minds, as it implied I didn't have enough money to
rent a space, ergo I must not be very successful, ergo I
must not be very good at my job. In a way, I believe
that working remotely at that point in time actually did
harm my early career prospects. I don't think it's still
quite the case, as people are beginning to realize that
some of those shaggy hipsters nestled up in the corner
of the coffeeshop are making triple the income as your
typical corporate keyboard warrior. Still, the older and
more traditional the industry, the more of a problem
you'll find in their acceptance of remote work as a
norm. If you're working in the SaaS (software-as-a-ser-
vice) startup world, it's a given and people won't think
twice. If you're working with toilet seat manufacturers
in Alabama, well, chances are they won't really under-
stand the concept of not having an office.
159

It’s worth reiterating the importance of networking.
Even with a more widespread acceptance of freelancing
as a legitimate career, you’re going to negatively affect
your trajectory if you never leave your home office.
Joining local communities and networking with peers is
crucial to both furthering your reach now, and for years
into the future.
Remote work is such a recent trend, that I don’t
think people often think about the long-term affects of
it. It may be working fine for you right now, but think
about a decade from now. Ensure that you’re fostering
relationships that will allow you to do the work you
want to do when you are forty, fifty, or sixty years old.
At that point, you might want to be in a managerial or
consultant role. Is your current social and business net-
work going to facilitate that?
160

Independence As A Remote Worker
Unfortunately, just because remote work is on the
rise, doesn't mean it's the new normal or even that
companies really know what to do with it. I've worked
for remote companies, worked with dozens of remote
clients, and now run a remote company, but every sin-
gle one of these use cases could use improvement.
While I think the field of remote work is improv-
ing, and over the course of the past ten years there has
been progress in recognizing some basic best practices
in operating a distributed team, it's still got a long way
to go. And as a worker in a remote company, you've
just got to deal with these struggles as they surface.
161

Your level of independence is usually a direct func-
tion of how far along you are in your career.
All jobs, regardless of where they're located, give
you a varying level of independence to structure your
own work day. There's not really a single entry-level
job, remote or not, that lets you graduate from high
school or college and start defining your own work
hours and responsibilities. Whether you're working in a
cubicle at a multinational corporation or from the com-
fort of your bedroom, an entry-level employee has to
endure a bit of drudgery and hunker down to do grind-
ing work. There's usually very little room left for cre-
ativity or independence or strategizing right out of col-
lege.
However, spend a few years at work, get promoted a
few times, and by the time you're in your mid thirties
you can usually get a bit more flexibility in how you
complete your responsibilities (and hopefully you've
also gained a few more responsibilities during that time
period). You probably travel for work a bit more often,
are able to implement more of your own ideas into your
workflow, or are involved in strategy. And even in the
162

strictest of corporate settings, you probably don't have
to worry about clocking in & out like you did a few
years ago.
The further you go in your career, the less your per-
formance is gauged by how long you were warming a
chair, and the more you’re gauged on the actual results
you've provided the company.
Why does this matter? As a remote worker, whether
we like it or not, your success depends on some of the
same metrics. A customer service employee is going to
be gauged by the amount of calls answered, problems
solved, and support cases resolved. A chief marketing
oﬃcer’s performance, on the other hand, is not going to
be gauged by how many emails or phone calls he re-
sponds to, but by Q2's marketing ROI or last year's
gross sales numbers.
All of that to say, there's only so much indepen-
dence anyone can expect at first: whether you're work-
ing from home or working in an oﬃce. If you're far
enough along in your career where you can have some
level of control over your job role and responsibilities,
things are suddenly much easier.
163

I think that remote work for mid-tier and upper-
tier employees, or in tech-driven fields (or really any-
thing that's new, skills-based, or disruptive) is a much
easier equation to solve than remote work in entry-lev-
el, traditional fields. If you're already forging ahead in
new unexplored waters, chances are there is a lot more
leeway given for both management and employees. A
department that hasn't changed very drastically in
many years - say, for example, customer service - is
much harder to deal with.
Remote work grants a large deal of independence
and self-direction to colleagues who are located out of
their home or coﬀee shops, and a good company will
judge these employees by their results rather than by
traditional metrics. Consider yourself fortunate if
you're employed at one of these companies.
The good news about remote work really shines if
you're a freelancer. There has been a massive uptick in
the amount of freelancers and consultants over the past
decade, and your location independence should actually
be a benefit instead of a hindrance in your career. No
longer do companies find it unusual that you work
164

from Starbucks or from your home oﬃce - it's actually
quite normal.
Adjusting to remote work is easy for some people.
And it’s even easier if you’re already the unorthodox
type that bucks the trend.
I was a weird kid in college. The good thing was, I
knew it. Self-awareness is important. But that doesn’t
change the fact that I was an incredibly nerdy dork who
didn’t fit in with the bros very well. And still hadn’t de-
veloped the ability to grow facial hair. That didn’t stop
me from trying. I remember hanging out with a group
and learning one of the guys was from Omaha. I
cracked a joke about Warren Buﬀet, the oracle of Om-
aha, and immediately killed the room’s vibe. The entire
group just stared at me.
I was a bit of a misfit, clearly, but I did well in
school. I worked a two or three part-time jobs while
juggling a full class load, and the busyness kept me
from procrastinating. I got over my initial awkwardness
and networked well. Yet here’s the deal: I didn’t learn
anything in any class. I quickly learned that the classes
165

themselves were irrelevant: I actually didn’t even have a
single sit-down class with my most influential professor.
The value of college came from two things: the pos-
itive aspect of being in a closely networked private uni-
versity environment, and the negative aspect of a terri-
bly old-fashioned, expensive, and ineﬃcient educational
system. Due to the frustrations of being in a one-size-
fits-all educational system I learned how to hack it, skip
a lot of crap, and graduate in three years while avoiding
the classes I didn’t want or need. I tried to carry this
lesson across into the real world: it turns out you actual-
ly can skip most of the stuﬀ you don’t like. You can
hack your career.
There’s no question about it: the current state of our
educational system is dysfunctional. Critiquing college
unequivocally across the board, however, is selling edu-
cation short. Like most things, it is what you make of
it. A traditional formal education seems to be more and
more unnecessary for the average driven, intelligent
young person. I’ve never once been asked about my de-
gree, even in the multiple traditional employee posi-
tions I held right after college.
166

My friends from college have ended up in a wide
variety of positions in life. I don’t think college really
influenced where they ended up: they would have got-
ten where they are one way or the other. I don’t really
even think their chosen major influenced anything, ei-
ther, because certain types of people are just naturally
drawn towards certain degrees. Causation rather than
correlation, perhaps.
But even if I think an undergraduate degree is a
good thing, in the end, it doesn’t really matter. What
you do with your situation - your education, your pre-
vious career, your future career, your networking - is all
entirely up to you.
I suspect that my taste of college was flavored with
my particular odd slant. As I mentioned before, I didn’t
fit in especially well. But it was still educationally
sound. I got a fairly decent academic scholarship. I
couldn’t have really asked for more. But because I didn’t
have a full scholarship, and because I felt that every se-
mester I didn’t spend in school was aﬀecting how much
I could do in actual life, I wanted to get it over with. It
didn’t help that I had started out in graphic design, and
167

quickly realized that unless I wanted to be perched in
front of an iMac designing hospital posters for the rest
of my life, I needed to get the hell out of there. So I
started looking for options.
Luckily, there was a new degree track introduced by
the Honors College at my university called In-
terdisciplinary Studies, which let students create their
own major by mixing and matching classes from several
disciplines. I applied and was the second student to be
accepted into the new program, and I spent the next
few weeks feverishly creating my own dream track and
getting it approved by the provost. I scratched biology
and calculus and added classes like Old & Middle Eng-
lish Literature, Abnormal Psychology, and Drugs, Alco-
hol & Crime.
Most of my professors were excited about the pro-
gram and helped me draft the program. A few profes-
sors got strangely pissed oﬀ and sent me angry emails.
One told me grimly “graduating early isn’t in my play-
book”, or “I will certainly not supervise”, or “there is
too much at stake in skill building, ideation develop-
ment and critical thinking formation to do it alone”,
168

and perhaps most impressively “you miss a lot of what
creativity is about when you approach life as a check list
to be completed as quickly as possible”.
In the ancient world these professors operated in,
there was no room for scribbling outside the lines. The
possibility of having a long, lucrative career without
ever going into the oﬃce was impossible to them. There
wasn’t much flexibility in their mindset.
I preserved these emails carefully, so I could reply
after I had completed the items on my checklist as
quickly as possible. I’ve yet to send that email, but I
plan on replying one of these days. As soon as I finish
that checklist.
Often you will find managers with this same mind-
set: they are stuck three decades back, in a world where
everyone buttoned up their suits and sent faxes. Taking
a diﬀerent trajectory, like working from Bali, rubs them
the wrong way. Unfortunately you will have to work
with these types just like anyone else, and grant them
understanding even if it’s not reciprocated.
Some of it just boils down to a cultural disconnect.
Whether you’re older or younger, an interest in remote
169

work means you’re operating on the vanguard of busi-
ness. It’s going to rub some folks the wrong way.
170

Finding A Remote Job
We’ve covered some of the fundamentals of how
managers can find remote employees, but how does an
employee find a remote job? It’s not as simple as revers-
ing the process, unfortunately.
The hard part about getting a remote job is not the
availability or lack of volume, of course - there are hun-
dreds of remote jobs opening up every day, and they’re
becoming available in more and more industries. The
trick is about getting noticed, and making sure you
stand out among the hundreds of other applicants…
because you won’t find a more competitive application
process anywhere outside of Silicon Valley itself.
171

It’s probably useful to give a behind-the-scenes look
at the hiring process that remote companies use. You’ll
quickly see that the key to success in getting a remote
role is to set yourself apart from the other applicants,
and getting a conversation going with someone at your
target company.
When we post a job opening at Discosloth, we
don’t just get a few dozen good applications. We get
hundreds in the first few weeks. Remote job opportuni-
ties are so in demand that our job postings automatical-
ly get scraped and syndicated across the web to twenty
or thirty remote job boards, and after a few months we
can get over a thousand applicants even for a niche po-
sition.
Just like we have a handful of important criteria
that every applicant needs to fulfill, every other compa-
ny out there is also looking for a specific person who is
perfect for their role. For an entry-level Google Ads
specialist, for example, we want to know that the appli-
cant fits with Discosloth’s vibe, has a well-defined hard
skillset, can work well remotely, and fits our salary re-
quirements.
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Are there a thousand quality applicants in the world
who fulfill our requirements? Perhaps, but out of our
group of a thousand applicants, we can filter them pret-
ty quickly. It’s a little disappointing, but I can usually
glance across a resume or CV and automatically filter
out 90% of the applicants within seconds simply be-
cause they don’t have the requisite skillset.
And that’s Lesson 1: apply only for relevant oppor-
tunities. The shotgun approach does not work well for
remote roles. This means that each application process
will be a little more time intensive and selective, but
spending extra time on personalizing your resume and
communication for each open role will probably serve
you better than spending time on applying to just any
random remote role that you see opening up.
Now that I’ve gotten our field of applicants nar-
rowed down to a hundred or so, after looking at their
skills, I then look at their experience. I’ll be upfront:
work experience doesn’t really matter that much to me.
But life experiences do matter, and they’re especially
relevant in a remote role. Some of the best applications
I’ve seen include details on their life experiences like
173

hobbies, interests, and especially travel. Taking a sum-
mer oﬀ to travel Asia, or spending a few months in col-
lege working in a ski resort, or running half marathons,
producing short films for your local film festival, work-
ing in foreign countries - all of those are things that in-
dicate you’re creative, daring, take risks, and can proba-
bly handle working from a distance.
And that’s Lesson 2: be personal and share your ex-
periences. Emphasize travel, personal independence,
and entrepreneurial pursuits.
After looking for candidates who have included
their personal experiences, I’m probably left with thirty
or forty solid resumes that tell a good story. I usually
have a hunch that all of these applicants would fit with
Discosloth’s vibe. This leaves me with the boring but
essential task of reaching out to every one of these pos-
sible applicants and doing a little back-and-forth before
inviting them to a preliminary interview.
That’s Lesson 3: Be prompt and reachable. You’d
think that all of these applicants would be interested in
a job, right? Wrong. The number one reason that we
pick someone else for an interview is because they actu-
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ally responded promptly. A surprising number of appli-
cants simply don’t get back to me, or if they do it’s four
days after I sent them an email. There is no excuse for
this, because every company is using this response time
as a gauge to see how engaged and punctual the appli-
cant is. If you can’t even get back to a company quickly
after they reach out to you, that’s a major red flag.
I’m probably left with 5-10 decent applicants at this
point - punctual, qualified, and interested. Ideally I’ll be
able to have a video interview with all of these appli-
cants, but realistically something comes up in the back-
and-forth that makes either the applicant or myself real-
ize we’re not a good fit. Salary, expectations, communi-
cation style, or simply not a great vibe.
As an applicant, I’d make it my priority to get into
that last round of video interviews. This is the most im-
portant of all sections of the job application process,
and the first video interview makes or breaks a hire. Make
yourself stand out, apply to highly relevant positions,
make your resume tell a personal story rather than a
collection of GPA scores and college classes, and be
professional and responsive to inquiries from the com-
175

pany.
Remember that you’re applying for one of the most
competitive types of positions ever, and you’re compet-
ing with people from every location in the entire world.
Used to be, you’re competing with others in your city.
With remote work, you now live in a city of billions.
176

Personal Downsides of Remote Work
When something new appears on the horizon, the
excitement in the air is palpable. You start seeing the
tweets, overhearing buzzwords in conversation, and in-
evitably some community bloggers on Forbes start pub-
lishing those articles about 5 ways to make your AI-
powered chatbot drive ten times revenue for your influ-
encer marketing business.
The same happened with remote work. The internet
got faster, and suddenly remote work exploded. Why
work from the oﬃce if I can work from home? Why
work from home if I can work from the beach?
I've been working remotely for a while now, so I
177

can't really blame anyone who's on board the same ship
I am. It's a quite nice ship. I’ve seen forty-odd countries
from the deck of this ship.
However, if we take a look at the life cycle of other
work related trends, you'll see a pattern develop. First
it's the hype. Then it's the implementation. Then it's
the reality.
For a long time open-plan oﬃces were hyped to us
as a perk - work in the same large airy, echoey space as
your CEO! - and it was, admittedly, pretty cool. But at
the same time it was an incredibly unpractical and
sometimes painful setup to work in. An entry-level em-
ployee like me didn't really need to hear the CEO argue
on speakerphone all day.
Over the past decade (man, doesn't time fly?) of
working remotely I have come to realize that remote
work might not be the magic bullet we first thought it
was. I still love remote work, but there are a plethora of
problems and downsides that need to be honestly faced
before you can make it work for yourself or for your
company.
As Discosloth has grown we have hired on remote
178

employees, both full-time and part-time. It's been a
learning experience. Thankfully, I think digital market-
ing is one of the most applicable fields for remote
workers. All of our time is spent on the internet any-
way. But I actually am not sure we will always be 100%
remote. I could visualize us transitioning into a tradi-
tional office sooner than later, if only for the luxury of
having a coffeemaker, water cooler, printer, and the
ability to separate my work life from everyday life.
I've worked remotely as a freelancer, as an employ-
ee, and as a boss. The dynamics are different in all three
roles, but the reality is that you can't treat it the same as
a normal job. I was curious how others feel about the
downsides of remote work. I know I'm weird, and my
problems probably aren't everyone's problems. Thank-
fully I've got an expansive network of folks working
remotely, and many of them were able to join in with
their thoughts.
Timothy Jensen is a PPC marketer, and works re-
motely just like we do at Discosloth. He said that the
“biggest downside can be maintaining boundaries be-
tween personal and work life. Particularly in a house
179

with small kids, it's important to have a separate space
for an office (for me, it's the basement) and clear
boundaries for when I'm at work and not available.”
We don't have kids in the house right now, but I
can see that being a game changer.
I met Holly Ragsdale around the same time I start-
ed working remotely, at a little coffeeshop outside the
college we both attended. She now works remotely as a
content lead for Booj Digital. Her response was similar.
She says the hardest part about remote work is losing
human contact. “But I remedy that with at least 1–2
coffee shop visits a week,” she says. “Breaking up the
week by being in a social setting has helped me tremen-
dously. I'm also spoiled in the fact that my husband
works from home (as a programmer) about 80% of the
time, so I don't get as lonely as I would if he had a
more traditional office job. Having a dog and taking
lots of walks helps too!”
Michael Bogosian runs Blacksmith Digital, an in-
ternet marketing company. He says “I'd say the biggest
downside to remotely working is the opportunity to
connect with other people and ride the wave of creativi-
180

ty that's often produced in a group setting. Video con-
ferencing does wonders to bridge the gap in many situ-
ations but nothing beats a power workshop in person
with your client/resource. The energy and satisfaction
can be palpable. I just don't get that from video, email,
chat, sms, or phone.”
I tend to agree with Michael. As much as software
companies like to tout their messaging and project
management solutions for improving remote commu-
nication, sometimes it’s just not enough.
Jordan Ayres says “For me, there are no downsides.
With that said, I have friends and colleagues who men-
tion that they miss being around people. It’s also worth
mentioning that I split my time between an oﬃce and
working remotely, so I’m not fully remote. Although
this would be my preferred work arrangement. But for
anyone who feels this downside, it’s important to social-
ize outside of work. I make sure I have fun stuﬀ to do
in the evening that involves spending time with real
people and not behind a screen, whether that’s going to
an improv class, jiu-jitsu, or even going for a drink with
a friend. I’d much rather spend less time socializing at
181

work and more time socializing outside of work.”
I then posed an either/or question to everybody. If
they had to pick between remote work or not remote
work for the rest of their life, which would they pick?
Timothy Jensen says “At this point, I would say I
would pick remote. I worked in an open office setting
in the past, and while there are positives in being face to
face with people you're working with, the negatives of
the distracting environment outweigh the positives for
getting work done. In the digital marketing industry,
it's just frankly not necessary to be in the same room all
the time.”
Michael Bogosian says “I've settled into an office
lately where I can close my door and have some privacy.
As a new parent, working from home just doesn't work
anymore. I still run my business with all my resources
and clients remotely. I just rely on one a central loca-
tion to set up shop more than I used to.”
I asked Jordan, who worked a few days a week from
home, if he noticed any difference in the amount or
type of work he gets done. “Yes. When I’m at home,
I’m more productive and the quality of my work im-
182

proves. This is because it’s much harder to be distracted
and it uses up less willpower and mental energy. As I
mentioned above, when I want to focus on a task, I
shut down all distractions. It’s easier to do this when
working from home.”
Holly said the same. “I would absolutely choose
remote work. In today's world, so much (and arguably
everything in the tech/writing/communication world)
can be done through the use of technology, so working
from anywhere makes so much sense to me. I also know
that I can handle working remotely after these two
years, so I feel confident that I could sustain it long-
term.” She also says that she sticks to a 9-5 in Central
Time while her team does 9–5 in Mountain Time. “We
are only an hour off so it hasn't affected us too much. I
do love being an hour ahead of them because I feel like
I've accomplished so much by the time they sign on,
and I just love that feeling of being ahead and on top of
things (rather than behind and catching up as soon as I
start work). All of our clients are in different time zones
(one of mine is Pacific and the other is Eastern), so it's a
lot to keep track of but it makes things interesting. I do
183

think keeping specific hours is helpful, so you don't feel
like your schedule for the day is unknown. It helps set a
healthy boundary between work and home life; when
5:00 hits, I do a good job of walking away from my
computer.”
We've all had one of those jobs - the demanding,
micromanaged, cog-in-a-machine grinding sort that
consumes your life inside the office and out.
Work/life balance is a popular topic these days, and
you’ll see lots of posts getting shared on LinkedIn about
burnout, treating yourself right, not checking your
email after five o’clock, and similar things.
Remote work puts a further layer of complication
on the subject. Because remote workers so often work
from home, it’s much more difficult to turn off your
work: especially if you’re across the world from the rest
of your team.
It’s a bit easier when you’re essentially in the same
time zone as the rest of your team, but when the entire
team is scattered between Bali, California, Spain, and
Russia, things start looking differently. Compromise is
184

required.
With the freedom and independence that remote
work gives you, much can be required: and this means
you can’t hold strictly to traditional work hours. Flexi-
bility is important, even if it means not working in the
morning, but having to work later into the evening.
This makes it difficult, at times, to turn work off.
How much you disconnect yourself from work is a per-
sonal choice, and depends upon how dedicated you are
to advancing a career. Personal priorities and a multi-
tude of additional environmental factors play into this.
Are you about to retire? Don’t worry about breaking
your back. Do you desperately need a raise or a promo-
tion? Might be worth the extra hours.
I’ve found that creating separation in your physical
environment is one of the easiest ways to mentally en-
capsulate your work.
Having a home office (not just a desk in your bed-
room, or a spot at the kitchen table) was one of the
most important things that helped me to clearly define
work time from non-work time. I can go into the office
and shut the door, sit down in my office chair, and
185

know that I’m at work.
If you don’t do this, it’s easy to be sitting on the
couch during the weekend, the same place where you
often work, and drift into sending some emails and
looking over the accounting. Just like it’s equally easy to
crash on the couch during work, and drift off into re-
searching cool weekend trips on the internet, or watch-
ing a YouTube video.
If you’re a traveling nomad (as I was for years) then
it gets a bit harder to create this physical separation.
You can rarely find the perfect Airbnb that includes a
home office. My solution to this is to go to coffeeshops
to work - even a few hours of focused work is usually
enough for me to get the vast majority of daily projects
done.
Sometimes, work just follows you around anyway,
and to a degree this is entirely okay.
Think about it from a broader perspective. If you
had a traditional office job, you’d be gone from eight in
the morning to six in the evening. You’d waste a lot of
time commuting, burn a lot of time goofing off at the
desk, and take an hour or more for lunch. It’s not terri-
186

bly eﬃcient.
Working from home, or from the road, frees up
hours and hours of your time. Perhaps you can’t divorce
yourself from work as easily as going home from a tra-
ditional oﬃce, but the upside is: you’re traveling. You’re
in Bali. Maybe having to work evenings isn’t so bad,
after all?
187

Remote Workflow &
Communication
189

When Process Gets In The Way Of Progress
Process in business is important. Process, when you
boil it down to the most crucial element, is the science
of making things happen. But the instant that process
suddenly gets in between your people and the goal, and
stops things from happening, is the instant that process
is your enemy.
Diﬀerent processes work for diﬀerent businesses.
Some businesses need next to no process. For example,
a yoga studio just requires that people show up, pay, sit
for a class, and leave. At best you'll need a schedule,
payroll, and a few bills each month that need to be
paid. An automobile factory, on the other hand, has
191

millions of intertwining processes that must be
matched together like clockwork. The two aren't even
comparable.
Remote work is not for the majority of companies.
If you're one of the 3.8 million retail businesses in the
United States employing 42 million workers, you can-
not work remotely. You've got a physical brick and
mortar store which requires people to show up to every
morning. The same with restaurants (15 million work-
ers) or factories (13 million workers). You simply can't
manufacture an automobile from a distance, and that's
why most traditional business wisdom doesn't apply to
remote work.
Companies that can successfully hire remote work-
ers are focused in a few very specific niches: services
(engineering, law, architecture), software (development
and IT), creative (design, writing, multimedia) and in-
ternet (ecommerce, publishing, marketing). Often even
larger physically based companies can incorporate re-
mote work into their workflow (for example, a manu-
facturer can turn their marketing department into a
remote team) but this ultimately requires the remote
192

team to follow the same processes as the physically
based company.
That's why the processes that have been working for
decades for traditional companies don't often work well
for remote teams.
A few years ago I worked with a colleague who was
obsessed with process. As part of the marketing team
taking charge of the content marketing strategy, he
would create elaborate spreadsheets carefully defining
schedules, painstakingly analyzing keyword lists, creat-
ing rubrics that assigned eﬃcacy scores to diﬀerent con-
cepts, detailing the titles of each and every blog post,
segmenting audiences into hyper-specific demograph-
ics, and so on.
Now, even ignoring the conversation on how smart
these tactics are anyway in today’s marketing world, this
colleague was missing a major point in dealing with a
remote team.
We happened to have a pretty fantastic remote
team. We had a solid analytics lead, a web developer,
and a content lead who worked extremely well together.
193

Even though we were in three entirely separate loca-
tions, each time we got together, we could brainstorm
ideas, create them, and then implement them in a mat-
ter of days or weeks. Our metrics were fantastic, and
the numbers just kept getting better. We were doing
solid work that we were proud of.
The key to our team's success was personality. We
worked well together (congeniality is incredibly impor-
tant) but we were also individually highly independent,
and could structure our days and priorities with little
oversight or input from others. We liked to work with
each other, but we were still able to get most of our
work done without too much micromanagement or
detailed guidance. In short, the perfect remote team.
When this colleague started bringing in a workflow
that he had become used to in his previous traditional
corporate job, he suddenly threw a wrench into the
works. The process was so onerous to a team of free-
thinking, independent workers that it killed the creativ-
ity and spontaneous thinking that had guided our work
so far. Instead of a balanced and respectful brainstorm-
ing session in which we would listen to the feedback
194

from team members and reach a common ground, we
were instead forced into a rigid workflow.
This colleague was a fan of agile methodology. Now,
there are tomes of thought already written about agile
workflow, enough that it's hardly worth revisiting, but
he imposed a structure on top of an already functional
team that essentially broke our productivity. As the
newly dubbed "sprint leader" he imposed spreadsheets
that documented everything, began scheduling too
many meetings to match with the phases of the sprint,
and essentially overrode our existing flattened hierarchy
a top-down hierarchy that didn't need to be there.
Projects that would take a month to complete were ei-
ther condensed into two-week lengths or cut complete-
ly. Projects that couldn't just fit into an Excel template
with a voting list of pros and cons were put to the side.
Our time spent in communicating things doubled, and
our actual output halved.
This colleague's error was in two assumptions.
First, he made the mistaken assumption that all
people work the same. He assumed that since this
process had worked somewhere else in the past, it
195

would work here as well. He did not realize that there
are many diﬀerent types of personalities, and some of
them don't require close task management.
Second, he made the error in thinking that micro-
management works in a remote team. He failed to real-
ize that the best remote teams actually need the least
direct management: after all, they are working by them-
selves, quite literally. They have no manager looking
over their shoulders. They have no standardized work
hours. They are probably some of the most independent
employees on the planet, and they will always do better
when they can take responsibility for their own output
and decisions.
Creating good processes for remote teams means
that you've got to understand your team, and the way
they work, before anything else.
Now, you can either create the process and hire
people for that process, or you can hire people and cre-
ate the process for them. One is going to be easier than
the other depending on your situation.
Since I believe good people are harder to find than
processes, my personal preferences is for creating a
196

process for the team, not a team for the process.
Because ultimately (and this is in direct conflict
with the advice suggested in many business manage-
ment books) the end question is whether things get
done. The process of just how it is done is totally irrele-
vant, and the more time you spend on the how means
you're not doing the actual it.
That's why I suggest hiring with your end goal in
mind. You want to have a remote team? Hire someone
who works well remotely, and that will always be some-
one who works well without oversight and microman-
agement. You want X done? Your employee already
works well without oversight, so the process required to
get X done should be as hands-free, time-efficient, and
independent as possible.
Jordan Ayres, whose thoughts I shared in a previous
chapter, works several days a week from home, balanced
by a few days spent at the office. I asked him how his
company manages remote work and institutes processes
for better productivity and efficiency.
“The fundamental philosophy,” Jordan says, “that
works for my paid media team, is to create and use
197

software, systems and processes that free up our time
and energy to focus on what clients pay us to do: im-
prove their performance. For example, our acquisition
team is split into two. There are both account managers
and executives. The account manager’s handle client
communication while the executives manage the client’s
paid accounts. This means that most of the time, as an
executive, I can focus on shutting down all distractions
and working on the account. I’ll only check my email,
Slack, or Asana if I need more information/have ques-
tions about the client’s business. I’ve found the key to
fostering communication and productive work is as fol-
lows. First, minimize distractions. Second, create pro-
cesses, checklists and systems. Third, schedule time for
“deep work”. Fourth, schedule internal meetings and
admin work when you have the least amount of energy
and creative output (mine is in the afternoon). And fi-
nally, focus on urgent and important tasks first.”
I asked the same question of Timothy Jenson. His
company uses a mixture of tools for communication,
using Skype for both group and individual chats. They
keep an orderly approach to document organization.
198

“In general,” Timothy says, “being available and respon-
sive during normal work hours is exceptionally impor-
tant when working remote (while at the same time re-
specting boundaries of personal time).”
Michael Bogosian has been working remotely full-
time for over eight years. “Communication has changed
throughout my career. It used to be exclusively through
email, text, chat, and phone calls in the beginning. I
relied heavily on Google's G-suite products and basic
management tools like calendar events. Now, we've
progressed into an age where I have 3-4 places I have to
check to respond to messages like Slack, Google Hang-
outs, LinkedIn, UpWork, Fiverr, etc. It's a little ridicu-
lous. Slack's use of channels makes interdepartmental
communications easier. It also allows me to set up
groups for specifics projects, which I like. I'm very
pleased with how G-suite has grown up. Google Drive
has become incredibly robust and interconnected. All
the products work well together and foster a great
amount of collaboration among remote teams. My gen-
eral philosophy around communication is to keep it
light. I am acutely aware of the lack of human connec-
199

tion with respect to body language conveyed via chat or
SMS. If there is a topic that requires me to truly under-
stand how someone feels about a strategy or approach I
prefer a video conference, or at minimum a phone call.
I try and use chat or SMS for tactical communications.
Same goes for my email. I tend to use email as a log of
what was discussed as opposed to a place where I devel-
op a strategy.”
A few years ago, I worked at a remote company that
tried hard at improving their process flow. They had not
always been a remote company, which means they had
inherited a long ancestry of traditional, corporate work-
flow that had morphed into a remote workflow.
Unfortunately, the company was just large enough
that the workflow had become fairly awkward. When
you go remote, you suddenly run into a lot of new
problems, chief of which is communication. The power
of watercooler talk is really underrated, and it turns out
that when you go remote, watercooler talk is eliminat-
ed.
I'm sure HR departments everywhere would love
200

that idea, but in reality it has a huge negative effect on
company communications. There is such a strong pow-
er in nonverbal communication that immediately stops
when a company goes remote, that there's no effective
way to communicate urgency or goals in the same
manner. Not only do employees get left in the dark
about important company movements, but managers
are clueless as to the small things that affect a team's
morale.
In an effort to increase the camaraderie and com-
munication between teams, the company instituted a
few platforms that were to ostensibly help stop this gap.
The company used OKR tools (to measure objectives
and key results), NPS polls (to measure net promotor
score), peer recognition (virtual high fives), Slack chan-
nels, coaching, and platforms that helped institute con-
tinuous feedback.
The problem is that among the half-dozen new
platforms each employee had to adopt, each ate up
hours of time each week, was easily gameable, felt artifi-
cial and corporate, and ultimately fractured the atten-
tion and emotions of everyone. Because, after all, no
201

one decides to work at a remote company because they
wanted a more corporate environment.
What would have worked in this company? Many
things, perhaps but what it was actually missing was a
simple hierarchical structure with a quarterly perfor-
mance meeting - you know, the sort of simple process
that has been in place for decades. And since this com-
pany was moderately sized, it was also lacking a regular
alternative for watercooler sessions. In short, there was
no unstructured time for employees to meet others in
the company, chat about goals, discover what other
people are doing, or just brainstorm ways to be better at
their jobs.
Too much process can kill the spirit of a company.
A crucial part of relationships, both professionally and
socially, involve conversation and casual chit-chat.
When you have less personal interaction anyway in a
remote company, dumping even more process into the
problem just exacerbates the issue.
202

Removing Time From Productivity
We've all had one of those jobs - the demanding,
micromanaged, cog-in-a-machine sort that consumes
your life inside the oﬃce and out.
Part of this is just the expected and normal career
path: right out of school, entry level workers have to
sludge through less-than-desirable positions until
they're promoted into a role that doesn't require de-
tailed management of work hours. Another part of this
is a systematically broken approach to productivity. It
changes entirely once remote work is brought into the
picture.
We still see this antiquated sort of vantage point,
203

every once in a while, when we bring on a consulting
client for our agency. We are results-focused rather than
process-focused, and we don't charge by the hour. Since
we're a vendor, not an employee, we charge a flat re-
tainer fee and deliver the results accordingly.
I think it's a pretty simple model (you pay us, we
give you something) but from time to time we've had
clients confused about our approach.
Some time ago, a long-term client switched up their
internal roles and a new point person was assigned to
our account. Although we had been nailing all of the
performance metrics for this particular client since the
beginning - improving on cost and volume goals every
single month - this new director of marketing didn't
seem to understand the concept of results-focused
work, rather than a corporate process. Almost immedi-
ately she began demanding a smorgasbord of informa-
tion: accounting for all the hours we were spending on
the project, weekly meetings to discuss strategies, using
her new task board instead of our internal scheduling,
sending countless emails, and worst of all, totally re-
vamping our own strategies.
204

We began spending so much time on red tape that
the actual project began suﬀering. Although we tried to
work with her on the communication process, it was
clear she wasn't interested in negotiating. I was con-
fused of her reasoning for weeks, until she shared her
screen one day and accidentally left her Notes app visi-
ble: a personal laundry list of complaints about our
company.
Reading this over, we realized that she was upset
that our company wasn't spending forty hours a week
on her project, but were still charging over double what
her salary was at the company.
Yet, our marketing consulting was directly respon-
sible for over 60% of the company's revenue. We'd
doubled their leads over the previous five months and
added hundreds of thousands of dollars of revenue.
How we tracked our time, processes, and strategies was
irrelevant, but she didn't seem to feel the same way.
Of course, this example isn't your standard employ-
ee to employer scenario, but I think it reflects the same
sort of mentality pervasive in the corporate world: a
focus on time rather than productivity. Just like an inef-
205

fective employee can generate a paperwork trail and
appear highly productive, a systemic focus on tracking
hours can also be a facade that hides actual productivi-
ty.
When you're working with a remote team, all of the
time-based productivity problems inherent in a tradi-
tional oﬃce are multiplied by ten. There are many rules
and guidelines that are negotiable with remote work,
but flexible working hours is not one of them.
Giving your team the ability and flexibility to work
whenever they want, on their own time, is one of the
most important things you can do for both their success
and yours. Here's why.
First, people who are going into remote roles are
looking for increased flexibility. Otherwise, they'd be
commuting into a normal job. Being locked down to a
certain range of working hours makes absolutely no
sense for the remote worker. For starters, this ties them
down to a specific time zone. If you're based on the
East Coast and require a typical nine-to-five working
day, these inflexible working hours make it almost im-
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possible for someone to work anywhere else than East-
ern Standard or Central time. What use is it to have a
remote job if you can't move to Pacific time if you want
to? You'll be required to work from 6am to 2pm every
day. Working from London would require an employee
to clock in from 2pm to 10pm every day. Neither of
which is an ideal schedule for everyone.
Second, having hourly-based expectations for your
team is priming you for disappointment (unless you're
running a customer support team or call center, of
course). Remote work already requires a significant
amount of trust and independence in both the team
and the individual employee. You are, hopefully, already
employing independent and ambitious high-perform-
ers. Forcing these high-performers to accommodate ar-
bitrary working hours is going to backfire. They should
already know what sort of schedule works for them per-
sonally, and it’s better to let them decide how they are
most productive.
Third, if you've got employees in diﬀerent time
zones, they're likely in diﬀerent cultures as well, none of
which operate on the same schedule as yours. Hiring an
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Italian is an excellent idea, but you shouldn't expect
them to be available at two in the afternoon, because
that is when every single Italian in the entire country
has popped down to the cafe for an espresso. Hiring a
Russian is also an excellent idea, but expecting them to
break for lunch at noon is bizarre: it's actually eaten
closer to three or four.
Time does not equal productivity. There's a lot of
research out there on the subject, but like most research
it always seems to conflict with each other. Companies
are not factories (well, unless they are factories, of
course). Unless your tasks are insanely menial, employ-
ees should be expected to ebb and flow in their produc-
tivity. Think about your own level of productivity
throughout the day, or even throughout the week. Do
you sit down at your desk at 9am on Monday and start
churning out a consistent level of work until 5pm on
Friday?
Of course not. Everyone's pattern of output varies.
In general, I'd say mine starts with a burst of productiv-
ity on Monday, getting back into the flow of business,
answering emails, starting small projects for the week. I
208

might get a little bogged down with work during the
middle of the week, going at a slower pace. Near the
end of the week I usually get a fresh burst, getting some
stuff done before Friday. Halfway through Friday, I'm
wiped out, and it's time to crack open a cold one
around lunchtime. I pick up the laptop a few times
during the weekend to get caught up on stuff that's still
happening and respond to any urgent emails. And then
the entire cycle happens over again.
Each day is even more granular. I love to get up ear-
ly and get the most urgent stuff out of the way, freeing
up my time later in the day for creative work (the part
of our business that I really enjoy). There are significant
dead times in the middle of the day where I don't get a
lot done - we take a long lunch, and usually there is an
hour or so mid-afternoon when I'm running errands or
taking a walk or doing something else that requires day-
light hours. Sometimes I work late into the night, other
times I’ve retired to the garage, fiddling with things by
four in the afternoon.
How many hours do I work during the week? Hon-
estly, I'm not really sure. Some weeks it could be twenty
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hours. Others it might be sixty. It's irrelevant. I get
things done when they need to be done. If nothing
needs to be done, I'm not under any pressure to do
anything.
This mindset isn't terribly structured, but in the
context of a remote company, it's essential. You're al-
ready working in locations scattered across the world:
why not work in all sorts of time periods, as well?
There are downsides that come with this approach,
as well, so it's important to analyze those. Here's some
of the reasons why this unstructured approach can be
tough to implement.
First, some companies and verticals require more
in-person communication than others. Whether that's a
phone call or a video call, this means that, at a mini-
mum, some level of overlap might be required. Most
companies work with this by establishing a minimal
amount of required working hours: for example, one of
the past companies I worked at required all employees
worldwide to be able to work from 8am to 10am Pacific
Time. This was actually a quite important rule for this
company, allowing teams located anywhere in the world
210

to be able to interface with each other without too
much focus on if a particular person would be available.
It was general knowledge that everyone would be avail-
able for those two hours during the day, and this fact
was known up front before joining the company.
Whenever I was in Central Time, I'd be available from
10am to noon. Whenever I was in Europe, I'd just shift
that ahead a few hours so that I was always available
between 6pm to 8pm. We have a similar rule at Dis-
cosloth, although we’re a bit more flexible about it.
Second, some roles and industries are still based on
hours. I think we’re all slowly evolving towards a better
and more results-focused mentality. Yet, you'll find
some backlash from people set in the old ways of calcu-
lating worth based on hours. Software developers still
have a strange knack of calculating their salary based
upon hours rather than value added to the company.
Even if they end up making the same amount of money
at the end of the year (or more!) it can be diﬃcult to
shift their approach from being paid on a time-spent
basis to being paid on a holistic results basis.
211

Triaging Communication
When you transition your team to asynchronous
communication, you'll find that your communication
process changes drastically. But it shouldn't be too
complicated: on the other hand, it actually becomes
significantly simplified.
Although we would love for these sorts of things to
work themselves out naturally (and they often do espe-
cially for very small teams) the reality is that, for a re-
mote team, some standards need to be set for how to
approach communication.
At previous companies I've worked at, there was not
really a standard company-wide policy (or set of guide-
212

lines) that helped people decide how to communicate.
The result was an often cluttered and ineﬃcient circle
of communication that got more complicated the more
people were involved. One person might send an email
about an urgent subject, and get upset that nothing was
done about it by the following morning. Another per-
son who loved talking face-to-face might call a video
meeting for something that actually didn't need to
happen for another month or so. Priorities would swift-
ly get out of whack, because employees (out of good
faith, to be fair) would focus on whatever was commu-
nicated in the most urgent fashion, rather than what
was actually urgent.
At Discosloth, we automatically avoid most of these
big communication issues by having small teams, but in
order to scale we have a triage system. It's quite simple.
Non-urgent tasks that need to be done eventually?
That's best done with an email. As is usual in the busi-
ness world, an email is expected to be answered within
one business day.
Moderately urgent tasks that need to be done now,
but probably not life-changing? That's best done with a
213

chat message. It's also a good way to have a discussion
about something technical. Email is too back-and-forth
for technical problems, yet you usually need a paper
trail to reference, which means that a phone call can be
difficult.
Urgent things that require immediate attention?
These are best communicated via a phone call or a
video meeting. It's also the best way to talk about any-
thing financially or personally sensitive - or whenever
something might involve heightened emotions.
I’ve floated our strategy around to various individu-
als who work in wildly different industries and roles.
I’ve not received unanimous agreement on my ap-
proach, which tells me that different strokes work for
different folks. Specifically, speaking with a team lead at
a software development company, I learned that he ab-
solutely hated email, and the rest of his team did as
well. Digging deeper into the reasons why, it surfaced
that their company used email tickets for bug requests
and support issues. Furthermore, the company decided
to implement communication based solely on Jira (a
software planning service from Atlassian that is focused
214

towards software companies using an agile methodolo-
gy). This software development company even required
their customers to sign up with a Jira account in order
to communicate with them.
I can identify a multitude of things wrong with this
approach, but the most prominent seems to be the
blanket aversion to email and the requirement that
clients adopt Jira. This makes sense for developers, but
not for the real world, in which customers aren’t always
tech-focused (if they were, they wouldn’t be calling you,
would they?) and definitely don’t know how to use Jira
eﬀectively. It’s worth taking a step backwards to analyze
just what’s happening with communication. The team
despised email, and rightfully so - as they used it, they
were having to keep track of countless issues, bugs, and
feature changes through email, a clunky medium for
constant feedback loops.
I consider that a total misuse of email. Unless you’re
discussing a new feature in a high-level, abstracted way,
I wouldn’t ever recommend using email when a team is
trying to figure out software bugs. Triaging this in our
manner would instead mean that the issue is best solved
215

asynchronously (likely via chat) or a ticketing system.
That is what drove them to adopt Jira. So far, so
good. They recognized email wasn’t working for bug
requests, so they moved to something a little more suit-
ed for that. The error, however, comes when they re-
quire all of their clients to also use the platform. That
might sound ideal, but this is a classic communication
disconnect between developers and customers. Devel-
opers don’t usually relish the idea of talking to anyone,
especially clients. Software people communicate far dif-
ferently than non-software people. Usually, between each
other a group of developers will do pretty well in con-
veying all the appropriate information, but throw an
outsider into the mix and it goes haywire. Shifting
communication platforms will not solve anything when
you have an underlying fundamental communication
flaw, and expecting your clients to use Slack or Jira in a
manner that meshes with your internal development
flow is a further mistake.
The solution to this would be to put a communica-
tor in between the developer and the client, which is
usually a good idea anyway. It’s a rare developer who
216

enjoys, or is good at, talking with the uninitiated. Too
many frustrations exist when one party of the conversa-
tion doesn’t understand fundamental tech-speak, and
the other party doesn’t understand fundamental busi-
ness-speak. Depending on the organization, that buffer
might be a project manager, a C-level officer, a sales ex-
ecutive, or a team lead.
There are some things you cannot change, and one
of those things is external communication. Anyone
who’s ever had a client knows that they’re the boss,
whether we like it or not, and the likelihood of training
them on a specific manner of communication is slim to
none. They’re paying us, after all, so part of our work is
communicating with them. It’s up to us to adopt to
their standard, not vice versa.
When we triage communication - three different
tiers of issues which are split between email, chat, and
direct communication - we use this internally, but not
necessarily externally. A crucial element of our entire
existence as a company means that we make it easier,
not harder, for our customers to communicate what
they need. Therefore, we bend to their needs and adjust
217

communication accordingly.
Some of our clients love email. Some of our clients
prefer chat. Some of our clients love the telephone. We
have a point person within the company designated as
the primary contact for each client, and we serve as the
mediator (the “account executive” for lack of a better
word) and translate the client’s communication into
whichever internal medium works best for the issue, so
the rest of the company knows what’s going on, as well
as the relative urgency of the issue.
218

Remote Technologies
It seems like every year brings another iteration of
software that promises to revolutionize the way busi-
nesses communicate. Slack, HipChat, Hangouts, Trello,
Asana, Superhuman, the list goes on eternally.
I once worked in a tool-obsessed company. We had
a tool for everything, and because the company was also
a bit corporate and overly obsessed with metrics, there
was a lot of everything. There was a tool to track com-
pany, departmental, and personal KPIs (key perfor-
mance indicators). There was a tool to track NPS (net
promoter score, which is a form of gauging customer
satisfaction). There was a tool to track time oﬀ. There
219

was a tool to track employee happiness. There was a
tool to collect anonymous employee sentiment and
suggestions. There was an app for the annual Secret
Santa. At one point they were even toying with the idea
of adopting an app that encouraged employees to pay
attention to their physical health.
On top of that, add hundreds of spreadsheets and
Trello and emails and Hangouts and Slack and a cus-
tom CRM and Zoom, and then again a few more spe-
cialized tools for each department. Simply onboarding a
new employee took months, and even then it was a
constant struggle to remember how to properly use all
of these tools in the course of an average workday.
Some level of tooling is critical to a company's con-
tinued success, especially as it scales. But I'm a big be-
liever in minimizing the amount of tools used in the
process. If it doesn't make you more money and time,
it's making you lose money and time.
The level of tooling at this particular company was
perhaps more suited to a company of 5,000 rather than
a company of 50, which will always have a lower rev-
enue, a greater margin of error, and more dependence
220

upon personal responsibility and productivity.
For most companies who are exploring the possibil-
ity of remote work, ideally you are a small and adaptive
group of workers. Simplicity is key. And more than
anything, quality communication is key.
In the end, you just need three forms of communi-
cation: visual, auditory, and literary. People need to
transfer words to other people. Just how those words
are communicated is mostly irrelevant, as long as they
arrive at the intended recipient and are responded to as
needed.
Although it's always a good idea to search for tools
and processes that speed up communication, cut down
misunderstandings, and improve eﬃciency, you must
always remember that new tools don't fix poor communi-
cation. If anything, adding new tools into the mix
makes poor communication even worse. Get your or-
ganization talking together in a productive manner
first, and then add the tools.
If your company is having problems communicat-
ing over phone and email, then the problems are not in
the mode of communication: the problem lies in your
221

company. Millions of companies have eﬀectively used
email and phone to communicate for decades. Adding
Slack or HipChat or Trello to the mix will not fix your
problems.
My pessimistic viewpoint on the importance of
tools has been often challenged by others in the startup
space, and it's good to listen to them as well. I'm not
always right (some would say I'm not always wrong)
and my opinion is just one of billions on earth.
However, I like gadgets as much as the next nerd,
and over the years we have structured a workflow that
works well for smaller remote companies. It's not very
glamorous, but it's simple and eﬀective. There's a
straightforward rubric for success when you’re adopting
processes and tools for communicating in a small re-
mote company.
My guidelines are: keep the cost per user down,
keep barriers to adoption low, minimize the ongoing
time required by the tool, encourage quality interaction
rather than quantity, and perhaps most important to
cap the amount of communication platforms to a total
222

of three or four.
Keeping the cost per user low is important, espe-
cially when considering the cost of scaling. It may seem
trivial to adopt a few platforms which cost $10-30 per
month for a seat. However, imagine a company in
which twenty users are on six or seven platforms each
(it sounds excessive, but I've seen companies with
more). Suddenly your small company is paying
$25,000 a year for monthly subscriptions that are actu-
ally making communication worse. If your company
scales to include fifty or sixty employees, you're sudden-
ly paying as much for the privilege of fancy spreadsheet
apps as for an entire full-time oﬃce manager position,
which might be a more eﬀective usage of your budget.
Barriers to adoption are also important to consider.
Tools only work well if everybody is using them, oth-
erwise you'll soon discover that some team members
will be out of the loop without even knowing it, simply
because they didn't see the message posted in the quar-
terly goals app a few weeks ago. And that means every-
one ends up resorting to email anyway, to pass along
the same information.
223

Ongoing investment of time is one of the least con-
sidered, but perhaps most costly of all, aspects of adopt-
ing tools. If each user spends just ten minutes a day per
platform, extrapolate for the whole year. Suddenly each
platform takes 41 hours a year, or an entire week of pro-
ductivity loss. Does each platform, in turn, provide your
company with over a week of value per user?
Encouraging quality of communication over quan-
tity of communication is also vastly important. Which
is more succinct and accurate: a detailed yet brief email,
or an endless group chat? Of course, diﬀerent ap-
proaches for diﬀerent beasts, but if we sit down and
analyze various methods of discussion I can rarely see
the benefit of a free-for-all, sentence-by-sentence chat-
storm approach to discussing a problem, rather than a
measured and slowly paced email exchange. Or better
yet, a simple phone call or video meeting.
And finally, capping the sheer number of imple-
mented communication platforms is probably a very
good strategy for smaller companies to keep in mind.
Accommodate the written word (emails for bigger is-
sues, chat for immediate non-intrusive communication)
224

and the spoken word (phone calls or video calls). You
really shouldn't need more than three or four platforms.
For example, within Discosloth we use internal email,
Google Chat, Zoom, and Google Calendar - that is all
that we need, and adding another platform into the mix
would just fragment things more.
225

Best Practices For Managing Employees
Remotely
Most of us with a few years of work under our belt
have had similar experiences, but I've experienced the
entire gamut of fantastic managers and terrible man-
agers. Likewise, if we polled everyone who has ever
worked under me, I think we'd have a similar range of
opinions that range from painting me in an angelic to
an absolutely demonic light.
At this point, I've worked more years remotely than
I’ve worked in a physical oﬃce. The dynamic is diﬀer-
ent, but it’s work all the same. And the more I work
with people, whether as a client or a vendor or a boss,
226

the more I suspect that being a good remote manager
isn’t that hard.
Acting in good faith, being diligent, paying atten-
tion to detail, and working hard to interact with your
employees on a personal basis is all that is required to
turn a dysfunctional remote team into a well-oiled ma-
chine. That's right: exactly the same sort of soft skills
that is required to make a traditional team located in a
central oﬃce work well together. Unfortunately, as we
all know, it seems like those soft skills are a little hard to
find. Remote or not.
A few years ago, I had a fantastic remote manager.
He would have been a fantastic manager anywhere,
though - there wasn't anything especially important
about the remote part. He was detailed, friendly, hard-
working, and most of all he acted in good faith. That's
not to say everything was perfect, but as far as manag-
ing a large number of people, it's safe to say this guy
was doing a great job.
As far as personality goes, him and I couldn't have
been further apart. If he was the moon, I was the Mari-
ana Trench. If he was a kale salad, I was a greasy break-
227

fast at Waffle House. That doesn't bode well for my
own chops as a remote manager, but I learned some
important things from him that I try to emulate in our
own company.
First, he was an excellent listener. Although I'm not
bad at listening (most introverted types are innately
good at taking a back seat and listening to other people
talk) there's always room to grow.
Second, he was supremely analytical. I'm much
more of a gut feeling sort of person - my intuition is
pretty decent, but I've learned more than once that I
shouldn't ever rely on it solely when it comes to impor-
tant, career-pivoting sorts of decisions.
Third, he was very process-oriented. I did not come
out of the womb a very process-oriented person, but it's
been a long evolutionary arc of learning to love the
spreadsheet.
Fourth, he documented exhaustively. This is one
thing, at least, I'm really good at. I write a lot.
Fifth, he was affable. I'm not known as the most
affable guy. Friendly, sure. Outgoing and able to chat,
sure. Affable? Not quite so much. If only there was a
228

button to change parts of your personality, right?
And sixth, he was extremely eloquent and graceful.
Eloquence and grace are like myths to me. They might
as well be the lost city of Atlantis. I've heard it exists
somewhere under the ocean, but don't depend on me
to tell you where it is.
All of these characteristics are important when
you're managing a remote team, because through your
various forms of communication (email, chat, video
meetings, phone calls) every little part of the manager is
amplified. Does he make people laugh in real life? In a
remote role he would be the manager comedian. Is he
slightly obnoxious in real life? In a remote role he is the
annoying guy everyone somehow forgets to acknowl-
edge whenever he joins the video call. Is he an obsessive
perfectionist? His emails will be enough to send his pe-
ons scattering in fear to their therapists.
One of the most important things to keep in mind
when you’re managing remote employees is that trust is
paramount. You’ve got a gulf separating yourself from
your team, usually both physically and chronologically.
If you can’t trust your team to make independent, self-
229

directed decisions, you can’t expect to find any level of
success in your remote projects.
Similarly, the employees in your organization must
trust the rest of their team, along with the hierarchy
above them.
A hands-oﬀ approach is essential, because there is
no practical way to have constant monitoring and
analysis of your team’s activity short of a live video feed
directly into their room. Believe it or not, that’s an ap-
proach that’s been used more than once, even if it’s
creepy and laughable.
Developing a company culture that encourages in-
dependence and creativity is incredibly crucial to a suc-
cessful remote team. This is a complex long-term
project that might be above the pay grade of the average
team member or department manager, but it’s essential
nonetheless.
Remote work doesn’t implement well when you’re
using antiquated approaches to business culture. You
can’t really expect a team of suited-up MBAs with a
corporate history at Goldman Sachs or Pricewater-
houseCoopers to make up your perfect remote team.
230

You’re inevitably going to have a team of misfits and
adventurers, who’ve had some strange career paths and
educational pursuits.
And that’s just fine.
231

An Afterword
As I mentioned in the very beginning of this book,
throughout the course of human history working from
home has always been the norm, rather than the excep-
tion. But remote work is a little diﬀerent than working
from home. There is an added dimension of being able
to marry productivity with travel, and it’s revolution-
ized the way people think about work.
A steady, solid remote career is possible. And it’s not
only possible to have a steady career, but it’s possible to
have a thriving career. When I started working remotely,
a few years after college, I was a freelancer mainly con-
cerned with making rent on time each month. Over a
232

decade of remote work since then, and my wife and I
have been able to see the same level of success than we
would have had in a traditional job (or perhaps even
more). We’ve had the freedom to quit our jobs, start a
company, travel to dozens of countries, buy a house,
hire employees, and still manage to relax and grab a
couple drinks on the weekend.
Remote work has spawned a cornucopia of new
ideas and new processes, some of them frustrating,
some of them delusional, and some of them a massive
improvement upon the status quo. It has spawned an
industry of travel influencers, balancing laptops upon
that pair of well-tanned legs, battling the blazing glare
of the sun on a beach somewhere in the South Pacific.
It has spawned a revolution in expectations from people
working in tech, marketing, or related information in-
dustries.
Chances are, if you work behind a computer screen
most of the time, your job can function in an either
entirely or partially remote manner.
And for those of you who manage remote employ-
ees, or are playing with the idea of going remote your-
233

self, learning how to deal with the intricacies of dis-
tributed work is essential.
The question isn’t so much if this will happen, but
when.
234

About the Author
Gil Gildner is an author and cofounder based in
Northwest Arkansas.
For several years, Gil worked as a freelance media con-
sultant for nonprofit organizations, carrying a bag of
camera gear throughout Europe, Africa, Latin America,
and Asia. After this, Gil worked as the director of spe-
cial projects for a fully remote startup, marketing luxu-
ry airfare and documenting a round-the-world trip with
18 flights in 40 days.
With his wife, Anya, he cofounded Discosloth, an en-
tirely remote search marketing & web analytics consult-
ing company with employees in both North America
and Europe. He has co-authored both Becoming A Digi-
tal Marketer, and The Beginner’s Guide To Google Ads.
He works from home, and has traveled to over 45
countries. You can find their website at:
www.discosloth.com
235

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