Real Talk: Why Honest Conversation Between Cofounders Matters

by Jason Shen, cofounder of Ridejoy and author of Winning Isn’t Normal

This is the third in a 6-part series on developing the habits that will make you a better startup founder. You may want to start with my first post: “How to Use Structure to Become a More Effective Entrepreneur.”

Founders often get into startups because we love technology and coming up with new ways to solve tough problems. We aren’t necessarily “people people.” We’d rather write code, fix engines, and wire motherboard than talk about our feelings.

Which is why this next habit is so hard, yet so crucial: Set up regular times to connect on an emotionally honest level with your cofounders.

Look, you’ve heard all the comparisons between starting a company and getting married. Cofounders are often like business spouses. You care a lot about the other person, value what they bring to the table, and count on them to share a lot of work and responsibilities. So if your cofounder(s) is like a spouse, it pays to understand what makes a great marriage work.

What Makes Great Marriages Tick?

Since 1986, a research professor at the University of Michigan named Terri Orbuch has been following 373 couples married that year and has interviewed them many times over the past 25+ years. Orbuch went on to write a book about her research and outlined the five steps based on what she learned about successful (and unsuccessful) marriages.

One of the steps she saw in successful marriages was that those couples would have frequent, often daily, briefings, where they’d talk for at least 10 minutes about something deeper than work or who’s going to do what around the house. Because if you don’t leave time for non-work and non-chore conversations, you lose something vital in the relationship.

If Orbuch, head of the longest running study on married couples ever conducted, thinks this is a really crucial practice for couples, why doesn’t the same hold true for cofounders?

You Only Think You Talk to Your Cofounder

A lot of founders will say “Why do I need to have a special time to talk to my cofounder? I see him/her everyday, and we talk about the business all the time.”

Oh yeah? Let me guess what those “about the business” conversations sound like:

Cofounder A: “Hey dude, you got a minute?”

Cofounder B: “Yeah sure. Oh, have you seen that bug that randomly resets user accounts? We should really get that patched”
Cofounder A: “Yeah, I did see that email. I couldn’t replicate it though. But anyway, I was thinking about what we’re doing.“

Cofounder B: “You mean what features we’re putting into the next iteration planning meeting?”

Cofounder A: “No, I mean about the startup. Do you think we’re tackling the right market with these mid-sized enterprise customers? I’m a little worried.”

Cofounder B: “Dude! Don’t you remember what that judge said at our last hackathon? He was all about SMBs. Isn’t he an angel investor? He must know what he’s talking about.”

Cofounder A: “I guess you’re right. Well, about that bug…”

Maybe that was a little bit of an exaggeration, but not by much. My guess is you’ve been on both sides of the conversation at different points.

Big deal, you say. Cofounder B is just trying to stay focused on the task at hand, right?

But what I told you that Cofounder A is also feeling burned out because she or he can’t meet the goal of pre-orders they set together, and also has ideas for a new product based on two dozen conversations with potential partners? How does that team make sure those (very real!) concerns get met and those ideas get surfaced?

Talking about Feelings Is Hard. So Use Structure

Remember the post that kicked off this series? It was called “How to Use Structure to Be a More Effective Entrepreneur”. Having open-ended, feelings-based conversations can be hard for technical founders. We did these at Ridejoy, but less often than I would have liked and without a great structure to hang it on. So I find it’s best if we create a framework to have them.

Here’s how to run a Real Talk session:

  • Set aside 20-25 minutes each week (depending on the number of cofounders) to do a talk. You can call it what you want
  • Go to a room, get outside the building, or do something that ensures you feel you have privacy and won’t be interrupted.
  • Each founder gets 5-7 minutes to check in. Suggestion questions: How are you feeling about the business? What are you excited about? What are you worried about? What do you wish we could change about how we’re interacting with one another?
  • Each founder gets 5-8 minutes to talk with absolutely no interruptions.
  • Once each cofounder has spoken, then a conversation can emerge about the issues discussed.
  • It’s possible you don’t have time to discuss everything now. That’s fine. If every conversation turns into an intense 3-hour therapy session, you’ll never make this practice a habit. Stop at the 25-minute mark and block off time on the calendar to talk more later.

Real Talk Matters

At the end of the day, the strength of your relationship with your cofounders is going to play a tremendously important role in the success of your startup. Y Combinator famously avoids investing in single founder startups, because the partners know how important it is to have someone else working alongside you as a peer.

If you want to keep that key relationship strong, then invest in the habit of having real talk conversations with your cofounder, and keep the spark alive.