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.
Most early-stage companies fail because of cofounder conflict. Here are 10 questions to help create alignment early.
Before you dive into the questions below, let me share what actually makes these conversations work—because I've seen too many founding teams skip this step and regret it later.
How to use these cofounder questions (so they actually work)
Here's the 3-step method I recommend: First, journal solo on each question. Take 20-30 minutes and answer honestly when no one's watching. Second, swap answers with your cofounder(s). Read their responses before you meet. Third, schedule 2-3 sessions of 60-90 minutes to discuss where you disagree or where answers surprised you. Don't rush this.
The output you're aiming for is simple: a 1-page "Cofounder Alignment Note" that captures your shared values, role boundaries, decision-making rules, and sacrifice boundaries. Keep it somewhere you can revisit when things get hard. Because they will.
One warning: do this before fundraising or first hires. Once you have investors or employees watching, the pressure to appear aligned makes it harder to be honest about misalignment.
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.
The 10 cofounder questions (grouped by theme)
These questions are by no means the end of the conversation, but they have the potential to provide a rich beginning.
Mission & values
This prevents the "we're building different companies" realization that shows up two years in. Get specific about what you're optimizing for—and what you refuse to compromise on.
1. What is your personal life mission, your reason for being?
Why it matters: If your personal missions don't overlap, the company will eventually force you to choose. Follow-up: What are 3 non-negotiables you bring from your life mission into this business?
2. What are your personal values?
Why it matters: Values conflicts create silent resentment that erodes trust over time. Follow-up: What do you refuse to optimize for, even if it costs you growth?
3. What is a story from your life where you were most being you?
Why it matters: This reveals what "showing up authentically" looks like for each person. Follow-up: What conditions in that story need to be true in this company for you to feel like yourself?
Success & sacrifice
This is where resentment starts if it's not explicit. Be honest about money targets vs. time freedom, lifestyle boundaries, risk tolerance, and family constraints.
4. What does success look like for you with this business?
Why it matters: "Success" means wildly different things—$10M exit vs. $100M vs. lifestyle business. Follow-up: What's your minimum financial outcome that makes the sacrifice worth it?
5. What are you willing to sacrifice for the success of this business?
Why it matters: Sacrifice mismatches (one all-in, one protecting family time) destroy partnerships. Follow-up: Are you willing to relocate if needed? How many years can you commit?
6. What are you unwilling to sacrifice?
Why it matters: Knowing boundaries prevents the "why aren't you working weekends?" conflicts. Follow-up: What would make you walk away from this company?
7. How can this business best support the life you long for?
Why it matters: If the business can't support both cofounders' lives, someone will leave. Follow-up: What lifestyle constraints (kids, health, location, relationships) shape your needs?
Support, feedback & conflict
Conflict is guaranteed. Repair is a skill. Get clear now on how you'll communicate when things get hard—because avoiding this conversation early guarantees painful conversations later. If you're already facing tension, learning how to navigate cofounder conflict can help you repair before it's too late.
8. What do you need outside of work to show up as your best self at work?
Why it matters: Burnout makes you a worse cofounder. Follow-up: What does "support" look like concretely—daily check-ins, weekly 1-on-1s, space to disappear?
9. What support from me do you need to show up as your best self?
Why it matters: Unspoken needs become unmet needs. Follow-up: How do you prefer to receive feedback—direct/blunt, or softer/framed positively?
10. What would you like me to start doing, stop doing, or change in order to be the cofounder you most need?
Why it matters: This creates permission for ongoing feedback. Follow-up: How should we handle conflicts when we disagree on major decisions? When those hard conversations need to happen, what ground rules help you stay open?
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.
Bonus: 50 cofounder questions (deep-dive list)
If you want to go deeper, here are 50 additional cofounder questions organized by category. Use these for ongoing alignment check-ins or when specific tensions surface.
Vision & Mission
- Why does this company need to exist?
- What problem keeps you up at night that this solves?
- Who are we building this for, really?
- What would make us shut this down?
- What does "changing the world" mean to you?
- What industries or use cases are off-limits for us?
- How do we want people to describe us in 10 years?
Roles & Decision-Making
8. Who is the CEO, and what does that actually mean?
9. How do we split responsibilities in the first year?
10. What decisions require unanimous agreement?
11. How do we handle tie-breaking when we disagree?
12. What are you exceptional at that I'm not?
13. What tasks drain you that energize me?
14. When do we bring in outside advisors to weigh in?
15. How do we decide when one of us isn't in the right role?
Equity & Money
16. How should we split equity, and why?
17. What vesting schedule makes sense?
18. Do we invest our own money upfront?
19. What happens if one of us leaves in year one? Year two?
20. What salary do we each need to make this sustainable?
21. How do we think about fundraising—bootstrap vs. VC?
22. What's our burn rate comfort zone?
23. Who manages finances day-to-day?
Work Style & Commitment
24. How many hours per week are we each committing?
25. Are we both full-time, or is someone part-time initially?
26. What does "urgent" mean for response times?
27. Do we work weekends? Evenings? Vacations?
28. How do we each recharge—alone time, exercise, family?
29. What's your natural rhythm—early bird or night owl?
30. How do you like to process decisions—talk it out or think solo first?
Risk & Sacrifice
31. What's your personal financial runway?
32. What happens if we don't raise funding?
33. How long can you go without a paycheck?
34. What would your family say about this venture?
35. Are you risking your marriage, health, or other relationships?
36. What's your Plan B if this fails?
37. How do we support each other if one person's life situation changes drastically?
Conflict & Feedback
38. How do we give each other hard feedback?
39. What does "fighting fair" look like for us?
40. Do we bring in a mediator/coach if we're stuck?
41. What behaviors are dealbreakers (dishonesty, etc.)?
42. How do we repair after a big conflict?
43. What's our cadence for alignment check-ins?
44. When do we escalate to our board or advisors?
Life Constraints & Personal Needs
45. Do you have kids, aging parents, health issues that limit availability?
46. Are you willing to relocate for the business?
47. What personal goals (marriage, travel, health) are you unwilling to delay?
48. How do we handle it if one of us has a mental health crisis?
49. What does work-life integration (not balance) look like for you?
50. What would you need from me to feel supported during your hardest season?
YC-style cofounder questions (the missing operational stuff)
Y Combinator and other accelerators focus on the operational alignment most founders skip. If you're serious about building a venture-backed company, answer these too.
Who is CEO, and what does that title mean?
One founder needs to own final decision-making authority. Even in a 50/50 split, clarity here prevents stalemates. What decisions does the CEO own outright? When does the CEO need cofounder consensus?
How did we arrive at our equity split?
Equal splits sound fair but often aren't. Who brought the idea? Who has more relevant expertise? Who's taking more financial risk? Who's full-time vs. part-time? Document the logic so resentment doesn't build later.
What's our vesting schedule, and why does it matter?
Standard is 4 years with a 1-year cliff. This protects the company if someone leaves early. It also signals commitment—if you're not willing to vest, you're not all-in.
What's our time commitment and runway?
Are we both full-time? If not, when does part-time become full-time? How many months of personal runway does each person have? Misalignment here kills companies when one person runs out of money.
How do we make decisions when we disagree?
Consensus is ideal, but what happens when you're stuck? Does the CEO break ties? Do you defer to whoever owns that domain? Do you bring in an advisor? Decide this now, not mid-crisis.
What's our hiring philosophy?
Fast growth vs. sustainable growth. Generalists vs. specialists. Culture fit vs. skills. Remote vs. in-person. These decisions shape everything. If you're already thinking about team building, knowing what role mismatches look like can save you from painful pivots later.
What's our approach to fundraising?
Bootstrap as long as possible, or raise pre-seed immediately? How much dilution are we comfortable with? What investor terms are dealbreakers? Do we want to build a $100M+ company, or is $10M a win?
How do we handle it if we can't work together anymore?
This feels dark, but it's essential. What does a graceful exit look like? How do we protect the company and each other? Having this conversation early—when you still like each other—makes it easier if things go sideways. If you're already at that point, this guide on reaching painful conclusions might help.
Questions to ask a startup founder before you join
If you're considering joining someone else's startup as a cofounder or early key hire, flip the script. Here are the questions you should ask them before you say yes.
1. Why are you building this, really? (Not the pitch—the personal reason.)2. What traction do you have? (Users, revenue, letters of intent—show me data.)3. How much runway do you have, and what's your burn rate?4. What are the 3 biggest risks that could kill this company?5. How do you make decisions—solo, consensus, or domain ownership?6. What's your working style—long hours, structured, or flexible?7. How do you handle conflict and feedback?8. What expectations do you have for my hours and availability?9. Why is this role open, and why me specifically?10. How are you thinking about equity and compensation?11. What does success look like in 3 months? 6 months?12. What happens if we realize this isn't working—how do we exit gracefully?
These questions protect you from joining a misaligned partnership. If the founder gets defensive or vague, that's data. If they're thoughtful and transparent, that's also data.
Frequently Asked Questions
When should cofounders discuss equity splits?
Before you build anything significant. The longer you wait, the harder the conversation gets. Equity splits should reflect contribution, risk, and commitment—not just who had the idea. Use a 4-year vesting schedule with a 1-year cliff to protect both parties.
How should cofounders split roles and responsibilities?
Start by identifying each person's strengths and what energizes them. One common split: one cofounder owns product/tech, the other owns growth/ops. Assign clear ownership for major areas (fundraising, hiring, product vision), but stay flexible in the early days. Revisit every 6 months as the company scales.
What if one cofounder is all-in and the other isn't?
This is a red flag. Mismatched commitment destroys partnerships. Have an honest conversation about time, money, and sacrifice. If one person can't go full-time yet, adjust equity and decision-making authority accordingly. If the gap is permanent, it might be better to part ways early or shift to an advisor relationship.
How often should cofounders revisit alignment?
Every 6 months minimum, or whenever something major changes (fundraising, pivot, new hires, personal life shifts). Use a simple check-in: Are we still aligned on vision, roles, and sacrifice? What needs to change? Regular check-ins prevent small misalignments from becoming company-ending conflicts.
How do cofounders handle conflict when they disagree?
Establish a decision-making framework before conflict arises. Options: CEO has final say, domain owner decides, or bring in a trusted advisor to mediate. The key is agreeing on the process early. When emotions run high, having a pre-agreed system helps you move forward without resentment. Learn more about how to manage hard moments with partners.
What cofounder questions does Y Combinator recommend?
YC emphasizes operational alignment: Who is CEO? How is equity split and vested? What's each person's time commitment? How do you make decisions when you disagree? What's your fundraising approach? These aren't philosophical—they're practical questions that prevent blowups later.
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
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