Tough Conversation Starter Pack
It's normal for cofounders to have different opinions about many (all?) of the different aspects of building a product and running a startup. After all, you are different people with different experiences trying to come together to accomplish a single thing. Having a different opinion than your cofounder about questions and challenges both large and small is not predictive of failure. What predicts failure is when cofounders avoid difficult conversations, lack the skill to negotiate differences as they come up, or do not have the capacity or will to find common ground and decide together on the path forward.
Below is a list of questions in areas that cofounders commonly disagree in. I encourage you to start discussing these questions now. As you do, keep in mind that your goal is not to find immediate agreement. Instead, I encourage you to note the areas in which you disagree, explore your differences as a team, and discuss the function of your disagreement. Ask questions like, "Where do our opinions both come from? What values are each of us using to form our opinion? When does this disagreement come up between us? How do our perspectives shape each of our execution and decisionmaking? Is this disagreement a problem for our product, team, or relationship today? If not, when will it become a problem in the future? (Reschedule the discussion for then.) Is our disagreement a dealbreaker for either of us? Why?"
Runway & Equity Split: Are we comfortable with our burn rate? Where should we spend less or more? How did we decide on our equity split? Are we 100% comfortable with it? Can we imagine a scenario in the future in which we won’t be? What’s our plan for that?
Users & Customers: Who is our user? Who do we want them to be? How do we deal with customer complaints? How should we? How do we channel user feedback into product management? Who’s responsible for the final product decision?
Performance: Is our workload even? What mechanisms are in place for providing feedback to each other? Is one person providing more hard or soft skills than the other? Is one skill set most important for our startup right now? Will one be more important in the future? Is one founder more or less dedicated/committed? Is that ok?
Features & Priorities: What’s the right release cadence? How do we prioritize what we build? Should we set aspirational, stretch goals or realistic, achievable ones? How much technical debt are we willing to accrue? How will we know when to hire? How do we decide which roles to hire for?
Roadmap: Are we using the right metrics? Are we hitting the right goals, or any goals at all? How much should we let users decide our roadmap vs our intuition? If not our users, which one of us? When do we know when to use data vs our gut?
Vision: What are our dreams for this company? Are they aligned? Do we believe in what we’re doing? What motivates each of us? What values are important to each of us? How important are our values to each of us?
Competition: Are we worried about someone else doing what we’re doing? Do we care? Should we? Do we feel urgency around competitors? Why or why not?
External Forces: Are either of us becoming distracted by external forces (a social life, family/kids/a partner, fundraising, press, etc.)? Are we choosing the right investors? Are we maintaining focus on our vision, or are we letting an investor/mentor pull us away? How much do we kowtow to others close to us (including our employees)?
Without getting too process-heavy too early-on, you might also want to come to an agreement about how you'll make decisions when cofounder opinion is split on some of these difficult topics. For example, will the technical cofounder always get the final word on product decisions? Keep in mind that it's inevitable that disagreement will arise, so having a decision-making framework in-hand before encountering a conflict means you'll have a map through the disagreement when it's happening.
