[Founder’s Real Talk #6] How to work with your cofounders

This is probably why my favoriate soccer team since I was 7 years old — Manchester United, sucks so much since Sir Alex Ferguson retired, especially in the first 2 games this season: it’s full of “leaders” (at least judging by their price tags), but not a team (they don’t know how to play together).

You probably saw this picture from Sequoia Capital’s famous series to startup founders during the current market downturn. It’s such a cliche tagline, but really struck me. Here's some more context:

Team of leaders: You likely have great leaders on your team. But a team of leaders who lead primarily for their own organizations does not always get the best outcome.

Leadership team: This is when your leaders think of their primary team as the one surrounding the CEO or founder every week. If your leaders think about the company’s executive leadership as their first team (as opposed to their individual functions as their primary team), you will likely have a better outcome.

I’ve seen many startups fail because of co-founder/leadership team issues and I’ve always wondered what can make them work better together. Now that I’m in the founder’s shoes myself, this question is always in the back of my mind, sometimes even in the front.

I’m fortunate enough to be working alongside some of the best leaders you can find in the world. We share the same vision and mission, we have leadership experiences, and we quickly built a startup from ground zero.

But we don’t have the textbook co-founders setup where, they either are family members (e.g. Stripe’s Collison brothers), went to school together (e.g. Airbnb's Brian Chesky & Joe Gebbia), or used to work together (many examples — probably the most common case).

So trying to figure out each other’s personality and workstyle became a thing that we either explicitly or implicily have been working on.

For me personally, I think these few things definitely helped. I’d love to share them here as a way to remind myself, and also to hopefully help my peer founders.

1. Overcommunicate. In the beginning, we tried talking on daily basis. We are all distributed across different timezones, so it wasn’t easy to fix time for regular sync communications. But it definitely helped. We try our best to provide context and share our thinking process when communicating, which was super helpful as we all come from different cultural and professional backgrounds.
2. Balance sync & async. For a lot of short updates and 1-sided debriefs, we use async communications (mostly written in Slack or email, but very often in video via mmhmm). This helps us to focus the sync time on interactive conversations, brainstorms, and even debates so that the time is used more efficiently.
3. Spend quality time together. Even if we are distributed, we manage to get together at least on quarterly basis. Each time is an onsite, where we spend a few days together working side-by-side and talk about everything from strategy to operations together, do some fun activities, have dinner and a few drinks, and get to know each other and each others’ families on a deeper level.
4. Personality tests. We all have done different versions of these throughout our careers, but recently I found 16 Personalities very insightful in providing guidance on styles of leadership, communication, and more importantly — what you get energy from (I’ll expand this point into a separate post later).

Of course there no proven success yet, but I honestly feel like we have been bonding and collaborating increasingly better. Also, as our leadership team is growing, it’d be interesting to test these out with the new members.