Boss or friend? How to support your team without crossing the boundaries

Running a small business inevitably means you become friendly with your team—even as the boss. This is less common in large corporations where the people at the top are far removed from most of the people who work for them. They can be feared, hated, or in the best companies, admired from afar.

Not so with my company; a small team of 6 including myself. We’re very close. It’s all part of the lifestyle business I run intentionally, not only for me but for my team.

Drawing the line of leadership vs friendship:

Formal vs informal

In most businesses your primary obligation is two-fold:

1. To be there for clients at normal working hours.
2. To make sure the team is in the right frame of mind to carry out their work to the best of their capabilities.

A good relationship with your team where you show vulnerability, openness and transparency will foster trust and the natural inclination to help you and each other is achievable by making sure all other things are in place:

• Share information readily with each other in a central place (such as Trello)
• Set up a process so the team does proper handovers before they take time off—this helps avoid unnecessary stress by ensuring team members have all the information to hand
• Meet regularly to create a clear picture of where the company is and where it’s going
• Communicate regularly about where you are with your client’s projects and business goals

Make sure these things are covered, and it will give you the freedom to have fun, chat and share in “non-work” things—health, relationships, plans, and everything else in life. 

When life and work collide

There will inevitably be times where people have a “bad day”, and this happens in all companies. Fostering a friendly environment gives people a safer space to share; usually, they don’t need more than just the offer of help, or words of support to have a good productive work day.

Putting that ego aside

If one of the team members is in a bad mood and takes it out on you, as the boss you have to be objective and mature, resisting the impulse to be defensive. Keep calm and measured, listen, ask questions, and try and understand where they are coming from. It can be healthy to allow them to vent about things if needed—showing you are on their side will make them feel more supported.

4 tips to help navigate the tricky boundaries of friend vs boss:

I am continuously very conscious of our work deadlines, obligations and tasks. My head is filled with all of the projects we’re working on, and I do very much like to know what’s going on with everything. Certain things have helped me navigate the tricky boundaries of friend vs boss.

Delegation of the “hard stuff”

Ideally, a member of your team (not you!) can take care of HR issues. The rest of the team can check in with that individual on working hours, booking holidays, contracts, organising performance reviews, and one-on-one meetings. This means you don’t have to be the person who runs around after everyone else nagging them about admin.

Team building trips and outings

We take a lot of “work trips” together. The business pays for flights and accommodation (with help from deals with various contacts and clients), and we all go together. The idea is that as long as we can keep on top of our client communications and deadlines we can be travelling together—learning, bonding and creating wonderful memories!

A formal structure for solving issues

We follow the “Entrepreneurial Operating System” (EOS) at TLD, which gives us a lot of good tools and structure. Everyone knows their role and we report on certain numbers weekly, which keeps things transparent and keeps us accountable. We focus on solving issues in our weekly team meetings. It’s a formalised approach that makes it easier to handle any touchy subjects or“elephants in the room”.

O3 and Same Page meetings

We schedule official meetings and this gives me a chance to meet with each member of the team in the “boss” capacity, one to one—also known as “O3 meetings”, something I learned about from the Manager Tools Podcast. O3 meetings are for generally checking in at how your team is doing. “Same Page” meetings are specifically about their projects and clients, and if they need support or help.

The fact that these are officially named formal meetings with a proper agenda keeps us on track, and we certainly don’t spend the whole time gossiping or planning “work trips”!

A final say

I think I have found a good balance, and choose to hang out with my team because I like them so much. We have traveled to and worked in eight different countries together. We have partied, solved problems, set goals, laughed, and cried. There are many more memories to make, and I do believe it has made us a better and more effective team.