10 Questions Every Cofounder Team Should Discuss

Most early-stage companies fail because of cofounder conflict.  Here are 10 questions to help create alignment early.

I was talking with a friend recently who cofounded a New York based startup. The company raised money from some big investors and got a bunch of press but failed to find significant market traction. They ultimately sold to a late-stage startup as an acquihire. As he was reflecting on what went wrong, my friend said:

We had it wrong from the very beginning. Even when it was just two of us, we didn’t talk about any of the hard things. We didn’t have any overt agreement on what we actually wanted out of the business. We didn’t talk about what success looked like for each of us. As a result, we were pulling in different directions from day one.

Startups are hard even when everyone is pulling in the same direction. When you can’t count on your cofounders as allies, startups are fucking impossible.

That conversation got me reflecting on my own experience as a cofounder.

I realized my experience was very much the same. We talked about starting a business so we could live by the beach and work with our friends, but that was about the end of our effort at cofounder alignment. When we found early success, raised our first million bucks, and began to see the ship get moving, even that early alignment strained.

As a coach, I now have the privilege to work with a range of early stage teams. One thing I love to dig in on early, in large part as a gift to my younger self, is cofounder alignment.

There’s a lot of research on families around the health of the children being tied to the strength of the parents’ bond to one another. I believe companies are much the same way. A healthy cofounder relationship provides the foundation for a strong company culture and thriving employees.

To that end, here are 10 questions I believe every team of cofounders should ask one another, take time to explore, and go deep on.

These questions are by no means the end of the conversation, but they have the potential to provide a rich beginning.

Journaling individually about each question is a great place to start. Talking openly with your cofounders about your answers will set you well ahead of the average founding team and give your company a firm footing for future growth.

1. What is your personal life mission, your reason for being?

2. What are your personal values?

3. What is a story from your life where you were most being you?

4. What does success look like for you with this business?

5. What are you willing to sacrifice for the success of this business?

6. What are you unwilling to sacrifice?

7. How can this business best support the life you long for?

8. What do you need outside of work to show up as your best self at work?

9. What support from me do you need to show up as your best self?

10. What would you like me to start doing, stop doing, or change in order to be the cofounder you most need?

If you are experiencing cofounder challenges, or if you’d simply like a dispassionate third party to help facilitate these alignment discussions, I’d love to meet you. Helping leaders feel less alone in the hard things is what I do.

Wishing you peace in your own journey today.

Matt