Managing your cofounder relationship for the long run

Your cofounder relationship can radically change the trajectory of your life. The relationship must withstand big stresses. You’ll occasionally share moments of discovery and achievement. You’ll often share problems. At the best a cofounder makes you your greatest every day. At the worst a cofounder sinks the company. How do you make such a critical relationship work?

I’ve run our company, SketchDeck, for the last two years and worked with my cofounder for three. I want to share what I’ve learned along the way.

The early days of the relationship

Founder relationships often start in exactly the wrong way: you start a company then hope the relationship works out. My first company was a frenetic experience; we (three cofounders) were all new to starting companies and quickly recruited each other because it seemed like the first step to making a company. We’d never really worked together, we just happened to want to start a startup at the same time.

We had a turbulent year. Half of it was spent working out what problem we were trying to solve. We built product, recruited investors, found clients, made many mistakes. We also discovered a widening gap between how we thought the company should be run. The gap turned into dispute, de-railed our seed round and ended the company.

If only we’d heeded Paul Graham’s warning. In retrospect, I think we all should have applied deeper critical consideration to who we founded with, similar to the rigorous evaluation of candidates when hiring. In those early days it seemed just one of a long list of risky decisions. It was actually the most important decision.

A good relationship

After the first company’s collapse I had the ingredients for a good cofounder: Somebody I knew I worked well with under stress and who had a similar approach to running a company.

My cofounder and I share a lot of viewpoints and approaches; we’re often surprisingly aligned on matters even though we’ve not had time to discuss them, preempting each other’s observations.

However we have enough difference in approach to challenge each other’s decisions in a constructive way. This brings broader consideration and validity.

I think this is the Goldilocks-value of similarity, and the most valuable aspect of our relationship.

The long run

Two years is a long time in a startup. Growth brings constant challenges to every aspect of what you do. Both of us as founders have had to change and develop, as has our relationship.

You have to dedicate effort to develop your relationship. Friendships often seem to maintain themselves, so it is easy to assume your cofounder relationship will do the same. Growth provides an endlessly increasing series of challenges most friendships do not have to endure. You must dedicate effort to support, uplift and develop each other.

Exchanging feedback is fundamental to a healthy cofounder relationship. Giving and receiving feedback in a way that develops your relationship is not straightforward or easy. Real feedback is emotionally exhausting, it’s challenging to integrate and requires you to open yourself up, trust, and commit to change. Giving effective feedback is a skill that you should develop*. It’s always hard to prioritise feedback (we take a weekend road-trip).

Feedback is such a catalyst for relationship development it bears repeating. Humans have endless avenues to misunderstand and upset each other, feedback maps them out.

The everyday complement to feedback is to communicate more. As the company grows your time with your cofounder shrinks; there are too many other people to deal with. It’s easy to replace communication with assumptions, however the latter rarely works as well. For high-volume information (e.g. features being released, work plans) we broadcast these on Slack and Trello, for important information (e.g. spending, hiring, absence) we ping short direct emails. I now spend time documenting product and technical direction and continually share it with the company. When in a reflective mood we ping each other essays of our thoughts, vision and concerns.

Over time we’ve had to make more space for each-other. In the early days we both got involved in everything: sales, marketing, support, product and tech. It worked well because nothing had form nor process, we were sprinting to keep up with it all. Now we’ve a maturing product and employees, that approach does not work. We’ve both had to let go of parts of the company, letting the other drive vision and execution.

In summary: Your cofounder relationship requires effort to maintain and develop, like any other part of the company. You need to exchange feedback, communicate and make space for each other. This seems like an obvious list of simple things, but doing these things well is hard and requires practice to do well every day. These are skills we can all improve on. Like everything else in startups, there are no silver bullets.

(*) You should explore and study feedback techniques. A very brief summary: Make feedback specific and talk about the affect of the other’s actions, not their intentions.