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1
How to create a roadmap
from scratch
www.rechartedterritory.com
2
A roadmap is like a travel itinerary in that in gives you a rough idea of how to go from where you are to where you want
to be, including stops you want to make along the way. It breaks down an overwhelming set of work into smaller chunks
that can be implemented over time to reach your vision.
What’s a roadmap?
A roadmap is a guide
Starting
point
Destination
(vision of the
future)
Roadmap
The roadmap is flexible (just like a good itinerary) so you can always make changes if you learn something new, but the
structure it provides can help you stay focused and maximize your time.
3
Rework could be required if short-term decisions are made
without knowledge of where the organization might go in
the future.
Rework
It will be difficult for your team or for other teams to
support the initiative if they don’t understand where you
are trying to go and how the effort will be phased. Just like
with your friends, springing something on them at the last
minute isn’t always successful.
Coordination issues
Without a roadmap, the future of the project could be at
the mercy of the whims of the day. Sharing a roadmap
helps to explain what’s coming and align your whole team
to that effort. By pointing to a roadmap, you can tell a story
of what the future could be and discuss how the new item
either complements or doesn’t fit into that narrative.
Direction shifts too often
Without a plan to reference, prioritization and decision
making can take a lot longer, especially if there’s a large list
of possibilities to sort through.
Delayed decision making
Just like working out or eating well, tracking progress
towards goals can help with compliance. If there’s no
roadmap or overview of your work, there’s potential to
move down multiple paths slowly, resulting in minimal
progress towards any one goal.
Slow progress towards goals
People like to be part of a broader purpose, so if they don’t
see the connection of their current work to the bigger
picture you might lose some of your best players.
Low team morale
What happens if you don’t have a roadmap?
Issues to watch out for
Does your team have a roadmap? If not, do you recognize any of these issues?
4
What’s an example of a roadmap?
Example roadmap
Phase 0
“As-is”
Phase 1
“Teacher resources”
Phase 2
“Local impact”
Phase 3
“National impact”
Students
Teachers
Parents
Worksheets
Customized
reports & tips
Group
programs
Tutoring
Homework
guides
Teacher/Parent
online portal
Here’s a sample roadmap for a fictional tutoring business.
Teacher/Parent
online portal
Tutoring apps
Aggregate
reports & tips
5
What are the parts of a roadmap?
The anatomy of a roadmap
Time scale
Categories Components
You can get creative with the formatting of your roadmap, but in general most roadmaps contain three major elements:
1) a time scale, 2) categories and 3) components. We’ll walk through more details about each one.
6
What are the parts of a roadmap?
Time scale
Phase 0
“As-is”
Phase 1
“Phase 1 title”
Phase 2
“Phase 2 title”
Phase 3
“Phase 3 title”
Category 1
Category 2
Category 3
Item B
Regardless of the roadmap
design, the time scale usually
runs with the near-term phases
on the left and the long-term on
the right.
3-5 phases is a good rule of thumb for
executive presentations and high-level
roadmaps. With more than that, people
can get lost in the details and the big
picture strategy gets muddled.
Item B
Item D
Item E
Item C
Item A
Item F
Item H
Item I
Item G
Item J
Starting with the current state
can help you see what you’re
working with. If you’re building
something from scratch then
start with Phase 1.
You could use phases, quarters,
months, dates, or the phrases “near
term”, “medium term”, and “long
term” to label your time scale.
Consider adding phase titles to
each phase to highlight the
theme. This content is also useful
for when you start publicizing
the changes to your customers.
7
What are the parts of a roadmap?
Categories/swimlanes
Phase 0
“As-is”
Phase 1
“Phase 1 title”
Phase 2
“Phase 2 title”
Phase 3
“Phase 3 title”
Category 1
Category 2
Category 3
Categories could be organized by
customer type, program, product, or any
other category.
Categories or “swimlanes” are
typically represented in
horizontal rows.
Item B
Item D
Item E
Item C
Item A
Item F
Item H
Item I
Item G
Item J
8
What are the parts of a roadmap?
Components
Phase 0
“As-is”
Phase 1
“Phase 1 title”
Phase 2
“Phase 2 title”
Phase 3
“Phase 3 title”
Category 1
Category 2
Category 3
Item B
Item D
Item E
Item C
Item A
Item F
Item H
Item I
Item G
Item J
This is the core of your roadmap.
Create a box for each initiative and
place it in the corresponding phase
and category. We’ll talk about how
to determine which phase to
choose in upcoming slides.
Fill in each box with the initiative title, value
proposition, product, service, or feature name.
Don’t forget any key research initiatives.
You could also add other information
such as goals, effort, value, etc. with
symbols, numbers, text, or color
coding.
Dependencies are typically indicated with a
solid arrow connecting the items.
9
First Step
Pick your roadmap
scope
Second Step
Organize your ideas
Third Step
Define your last
phase
Fourth Step
Define your first
phase
Fifth Step
Build out the
roadmap
Sixth Step
Build, measure,
learn, and adapt
How do I make a roadmap?
Overview of the process
10
A roll-up of all of the work you’ll be doing over
time to create new products for your customers.
Product Development Roadmap Product Roadmap
A view of all of the current and planned initiatives
for improving your customer relationships.
Customer Relationship Roadmap
All of the backend work needed to keep your
business humming and scalable.
Operations Roadmap
Product Roadmap
Consulting Roadmap
Marketing Roadmap
Infrastructure Roadmap
Training Roadmap
This graphic illustrates an example of how you could decompose the work you’re doing into different roadmaps.
Towards the right, you have your most detailed and specific roadmaps. Those could be consolidated into a combined
view within a particular theme, such as the examples in the middle. And finally, at the far left you have your enterprise
roadmap. Generally, detail increases from left to right and the type of detail is tweaked to appeal to the needs and
interests of decision makers who will be viewing the roadmap (ex. CEO vs. department lead, vs. team lead).
First Step: Pick your roadmap scope
Think about a hierarchy of roadmaps
Enterprise
Roadmap
11
By customer type
For example, if your
product or business serves
doctors and patients, try
drawing out a roadmap just
for the initiatives serving
doctors.
By organizational
structure
If you work in a department
within a larger organization,
make a roadmap that only
depicts what your department
plans to accomplish.
Alternatively, create a high-level
view of everything going on in
the organization.
By product or
product line
Maybe your business
includes selling both apparel
and apps. You could split
your plan out into two
different product roadmaps.
By goal
Try out building a roadmap
just including items related
to improving one metric.
Examples could be
improving education levels
or increasing profits.
First Step: Pick your roadmap scope
Some options for narrowing your scope
12
Sub-steps
Second Step: Organize your ideas
Plot value vs. complexity
Value
Complexity
Phase large and
valuable initiatives
Implement
quick wins
Avoid spending time
or $ on anything low
value and complex
Defer low value,
simple changes
a) Draw out a value vs. complexity
chart on a whiteboard or a large
sheet of paper.
b) Write each relevant idea on a
3”x3” post-it.
c) Use a value framework or dot
voting to determine the relative
value and complexity of ideas.
d) Review the high value/complex
initiatives. Brainstorm ways to
break them apart or radically
simplify the solution without
sacrificing value.
13
Third Step: Define your last phase
Figure out where you want to end up
Phase 0
“As-is”
Phase 1
“Phase 1 title”
Phase 2
“Phase 2 title”
Phase 3
“Phase 3 title”
Category 1
Category 2
Category 3
Item I
Item G
Item JPut your most complex, highest investment,
yet still valuable initiatives in this phase. Good
candidates are anything that requires a lot of
organizational buy-in, investment, or is
dependent on the framework set up in earlier
phases.
Put your most complex, highest investment,
yet still valuable initiatives in this phase.
Anything that requires a lot of organizational
buy-in, investment, or is dependent on work
to be completed in earlier phases.
This is also a good phase for any “nice to
haves” or final upgrades that are slightly
lower value.
14
Fourth Step: Define your first phase
Pick a starting place
Phase 0
“As-is”
Phase 1
“Phase 1 title”
Phase 2
“Phase 2 title”
Phase 3
“Phase 3 title”
Category 1
Category 2
Category 3
Item B
Item D
Item E
Item A
Item I
Item G
Item J
Describe your current state here. If you
are building something completely new
then you can remove this column.
Put your easiest, high value wins in the
first phase.
Make sure to add in methods to
capture data so you can adjust future
phases if necessary.
15
Fifth Step: Build out the phases
Complete the roadmap
Phase 0
“As-is”
Phase 1
“Phase 1 title”
Phase 2
“Phase 2 title”
Phase 3
“Phase 3 title”
Category 1
Category 2
Category 3
Item B
Item D
Item E
Item C
Item A
Item F
Item H
Item I
Item G
Item J
Fill in the middle phase(s) with
anything that builds on phase 1 but is
less complex than items in the last
phase.
Don’t hesitate to move items between
phases as you identify dependencies.
A good goal is for each phase to
have a cohesive theme. Fill in all of
the phase titles once you’re happy
with the setup.
16
Sixth Step: Build, measure, learn, and adapt
Map out paths to alternative futures
Starting
point
Destination B
(alternative vision of
the future)
Roadmap B
Destination A
(vision of the
future)
Roadmap A
Do you have lots of ideas of where you could end up? Go through the roadmapping exercise again, this time outlining a
path to an alternative end state.
17
Sixth Step: Build, measure, learn, and adapt
Track your progress and make adjustments if necessary
Starting
point Destination B
(alternative vision
of the future)
Roadmap B
Destination A
(vision of the
future)
Roadmap A
Roadmap A
As you start moving down any roadmap set up opportunities to continually learn and gather feedback. Then you can
review the data to decide if you should continue down your original roadmap or pivot to another one.
18
To achieve great things two things are
needed; a plan and not quite enough
time.
— Leonard Bernstein, Composer
How will you use your roadmap to achieve great things?
www.rechartedterritory.com

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How to create a roadmap from scratch

  • 1. 1 How to create a roadmap from scratch www.rechartedterritory.com
  • 2. 2 A roadmap is like a travel itinerary in that in gives you a rough idea of how to go from where you are to where you want to be, including stops you want to make along the way. It breaks down an overwhelming set of work into smaller chunks that can be implemented over time to reach your vision. What’s a roadmap? A roadmap is a guide Starting point Destination (vision of the future) Roadmap The roadmap is flexible (just like a good itinerary) so you can always make changes if you learn something new, but the structure it provides can help you stay focused and maximize your time.
  • 3. 3 Rework could be required if short-term decisions are made without knowledge of where the organization might go in the future. Rework It will be difficult for your team or for other teams to support the initiative if they don’t understand where you are trying to go and how the effort will be phased. Just like with your friends, springing something on them at the last minute isn’t always successful. Coordination issues Without a roadmap, the future of the project could be at the mercy of the whims of the day. Sharing a roadmap helps to explain what’s coming and align your whole team to that effort. By pointing to a roadmap, you can tell a story of what the future could be and discuss how the new item either complements or doesn’t fit into that narrative. Direction shifts too often Without a plan to reference, prioritization and decision making can take a lot longer, especially if there’s a large list of possibilities to sort through. Delayed decision making Just like working out or eating well, tracking progress towards goals can help with compliance. If there’s no roadmap or overview of your work, there’s potential to move down multiple paths slowly, resulting in minimal progress towards any one goal. Slow progress towards goals People like to be part of a broader purpose, so if they don’t see the connection of their current work to the bigger picture you might lose some of your best players. Low team morale What happens if you don’t have a roadmap? Issues to watch out for Does your team have a roadmap? If not, do you recognize any of these issues?
  • 4. 4 What’s an example of a roadmap? Example roadmap Phase 0 “As-is” Phase 1 “Teacher resources” Phase 2 “Local impact” Phase 3 “National impact” Students Teachers Parents Worksheets Customized reports & tips Group programs Tutoring Homework guides Teacher/Parent online portal Here’s a sample roadmap for a fictional tutoring business. Teacher/Parent online portal Tutoring apps Aggregate reports & tips
  • 5. 5 What are the parts of a roadmap? The anatomy of a roadmap Time scale Categories Components You can get creative with the formatting of your roadmap, but in general most roadmaps contain three major elements: 1) a time scale, 2) categories and 3) components. We’ll walk through more details about each one.
  • 6. 6 What are the parts of a roadmap? Time scale Phase 0 “As-is” Phase 1 “Phase 1 title” Phase 2 “Phase 2 title” Phase 3 “Phase 3 title” Category 1 Category 2 Category 3 Item B Regardless of the roadmap design, the time scale usually runs with the near-term phases on the left and the long-term on the right. 3-5 phases is a good rule of thumb for executive presentations and high-level roadmaps. With more than that, people can get lost in the details and the big picture strategy gets muddled. Item B Item D Item E Item C Item A Item F Item H Item I Item G Item J Starting with the current state can help you see what you’re working with. If you’re building something from scratch then start with Phase 1. You could use phases, quarters, months, dates, or the phrases “near term”, “medium term”, and “long term” to label your time scale. Consider adding phase titles to each phase to highlight the theme. This content is also useful for when you start publicizing the changes to your customers.
  • 7. 7 What are the parts of a roadmap? Categories/swimlanes Phase 0 “As-is” Phase 1 “Phase 1 title” Phase 2 “Phase 2 title” Phase 3 “Phase 3 title” Category 1 Category 2 Category 3 Categories could be organized by customer type, program, product, or any other category. Categories or “swimlanes” are typically represented in horizontal rows. Item B Item D Item E Item C Item A Item F Item H Item I Item G Item J
  • 8. 8 What are the parts of a roadmap? Components Phase 0 “As-is” Phase 1 “Phase 1 title” Phase 2 “Phase 2 title” Phase 3 “Phase 3 title” Category 1 Category 2 Category 3 Item B Item D Item E Item C Item A Item F Item H Item I Item G Item J This is the core of your roadmap. Create a box for each initiative and place it in the corresponding phase and category. We’ll talk about how to determine which phase to choose in upcoming slides. Fill in each box with the initiative title, value proposition, product, service, or feature name. Don’t forget any key research initiatives. You could also add other information such as goals, effort, value, etc. with symbols, numbers, text, or color coding. Dependencies are typically indicated with a solid arrow connecting the items.
  • 9. 9 First Step Pick your roadmap scope Second Step Organize your ideas Third Step Define your last phase Fourth Step Define your first phase Fifth Step Build out the roadmap Sixth Step Build, measure, learn, and adapt How do I make a roadmap? Overview of the process
  • 10. 10 A roll-up of all of the work you’ll be doing over time to create new products for your customers. Product Development Roadmap Product Roadmap A view of all of the current and planned initiatives for improving your customer relationships. Customer Relationship Roadmap All of the backend work needed to keep your business humming and scalable. Operations Roadmap Product Roadmap Consulting Roadmap Marketing Roadmap Infrastructure Roadmap Training Roadmap This graphic illustrates an example of how you could decompose the work you’re doing into different roadmaps. Towards the right, you have your most detailed and specific roadmaps. Those could be consolidated into a combined view within a particular theme, such as the examples in the middle. And finally, at the far left you have your enterprise roadmap. Generally, detail increases from left to right and the type of detail is tweaked to appeal to the needs and interests of decision makers who will be viewing the roadmap (ex. CEO vs. department lead, vs. team lead). First Step: Pick your roadmap scope Think about a hierarchy of roadmaps Enterprise Roadmap
  • 11. 11 By customer type For example, if your product or business serves doctors and patients, try drawing out a roadmap just for the initiatives serving doctors. By organizational structure If you work in a department within a larger organization, make a roadmap that only depicts what your department plans to accomplish. Alternatively, create a high-level view of everything going on in the organization. By product or product line Maybe your business includes selling both apparel and apps. You could split your plan out into two different product roadmaps. By goal Try out building a roadmap just including items related to improving one metric. Examples could be improving education levels or increasing profits. First Step: Pick your roadmap scope Some options for narrowing your scope
  • 12. 12 Sub-steps Second Step: Organize your ideas Plot value vs. complexity Value Complexity Phase large and valuable initiatives Implement quick wins Avoid spending time or $ on anything low value and complex Defer low value, simple changes a) Draw out a value vs. complexity chart on a whiteboard or a large sheet of paper. b) Write each relevant idea on a 3”x3” post-it. c) Use a value framework or dot voting to determine the relative value and complexity of ideas. d) Review the high value/complex initiatives. Brainstorm ways to break them apart or radically simplify the solution without sacrificing value.
  • 13. 13 Third Step: Define your last phase Figure out where you want to end up Phase 0 “As-is” Phase 1 “Phase 1 title” Phase 2 “Phase 2 title” Phase 3 “Phase 3 title” Category 1 Category 2 Category 3 Item I Item G Item JPut your most complex, highest investment, yet still valuable initiatives in this phase. Good candidates are anything that requires a lot of organizational buy-in, investment, or is dependent on the framework set up in earlier phases. Put your most complex, highest investment, yet still valuable initiatives in this phase. Anything that requires a lot of organizational buy-in, investment, or is dependent on work to be completed in earlier phases. This is also a good phase for any “nice to haves” or final upgrades that are slightly lower value.
  • 14. 14 Fourth Step: Define your first phase Pick a starting place Phase 0 “As-is” Phase 1 “Phase 1 title” Phase 2 “Phase 2 title” Phase 3 “Phase 3 title” Category 1 Category 2 Category 3 Item B Item D Item E Item A Item I Item G Item J Describe your current state here. If you are building something completely new then you can remove this column. Put your easiest, high value wins in the first phase. Make sure to add in methods to capture data so you can adjust future phases if necessary.
  • 15. 15 Fifth Step: Build out the phases Complete the roadmap Phase 0 “As-is” Phase 1 “Phase 1 title” Phase 2 “Phase 2 title” Phase 3 “Phase 3 title” Category 1 Category 2 Category 3 Item B Item D Item E Item C Item A Item F Item H Item I Item G Item J Fill in the middle phase(s) with anything that builds on phase 1 but is less complex than items in the last phase. Don’t hesitate to move items between phases as you identify dependencies. A good goal is for each phase to have a cohesive theme. Fill in all of the phase titles once you’re happy with the setup.
  • 16. 16 Sixth Step: Build, measure, learn, and adapt Map out paths to alternative futures Starting point Destination B (alternative vision of the future) Roadmap B Destination A (vision of the future) Roadmap A Do you have lots of ideas of where you could end up? Go through the roadmapping exercise again, this time outlining a path to an alternative end state.
  • 17. 17 Sixth Step: Build, measure, learn, and adapt Track your progress and make adjustments if necessary Starting point Destination B (alternative vision of the future) Roadmap B Destination A (vision of the future) Roadmap A Roadmap A As you start moving down any roadmap set up opportunities to continually learn and gather feedback. Then you can review the data to decide if you should continue down your original roadmap or pivot to another one.
  • 18. 18 To achieve great things two things are needed; a plan and not quite enough time. — Leonard Bernstein, Composer How will you use your roadmap to achieve great things? www.rechartedterritory.com