20 questions to ask a potential cofounder, and what the answers tell you

Most published lists of cofounder questions are full of questions with an obvious right answer. "How do you handle pressure?" gets a polished reply from almost anyone.

This guide groups 20 questions by what they reveal, each with what to listen for and what should make you pause. It is for the stage where you are still deciding whether to build together.

How to ask so the answers mean something

Asked about the future, people describe the person they hope to be. A real past event is much harder to dress up.

Research on predicting behaviour supports asking for both. Past behaviour is a strong guide when the situation is familiar, while in unfamiliar situations intentions carry more weight (Ouellette and Wood, 1998). A new company is unfamiliar ground, so ask for both and watch the gap between them.

Four ways to make a question harder to fake:

• Ask for the most recent time. A real event comes with a who, a when and a what.
• Ask for the belief, then the proof. "What won't you compromise on?" then "When was that last tested?"
• Ask for both extremes. Nobody can give the flattering answer twice.
• Ask what others would say. It moves the answer outside their own head, and you can check it later.

Ground rules

• Not on the first call. The first conversation decides whether there is a second. Bring these in after that.
• Write first, talk second. In First Round's founder dating playbook, each person answers alone before comparing. Gloria Lin puts a careful first pass at two to three hours, discussed over three to five in-person sessions.
• Follow every story. True stories gain detail under follow-up questions; rehearsed ones lose it.
• Answer them yourself. Every question works both ways.
• Limit your deal-breakers. Lin recommends no more than three.

Why they want to do this

1. What made you decide to start something now, and what would you be doing otherwise?

• Listen for: a concrete trigger, such as savings in place, a role ending or a problem they have lived with.
• Pause if: the only reasons are escape, money or being their own boss.

2. If this works, what does your life look like in five years? If it fails, what have you lost?

• Listen for: an honest picture of both outcomes, even if it differs from yours.
• Pause if: the answer drifts toward whatever you just said, or failure is "not an option".

Time, money and place

3. How many hours a week can you give this today, and in six months?

Founder Institute's list asks about commitment now, in six months and in two years.

• Listen for: a number, the days and times, and what they are giving up to find them.
• Pause if: "whatever it takes" with no number, or a number their job and family can't support.

4. What has to happen before you go full-time?

• Listen for: a named milestone, such as paying customers, with a rough date and a plan to reach it.
• Pause if: "once we raise" with no plan to get there.

5. How many months can you live without a salary?

• Listen for: a number based on their savings and obligations.
• Pause if: they have never worked it out, or need a full salary from month one with no plan to fund it.

6. Where will we each be based, and how often will we work in the same room?

• Listen for: where they live, whether they would move, and how often you would meet.
• Pause if: they assume you will move, or brush past time zones.

7. What else is competing for your time?

• Listen for: jobs, family, side projects and anything in their employment contract that limits outside work, all said up front.
• Pause if: commitments surface later, or they have never checked their contract.

How they work

8. Describe a working week that would feel terrible to you. Now one that would feel ideal.

• Listen for: specific details for both, and curiosity about yours.
• Pause if: their ideal is far from yours and they see no issue.

9. When did someone who knew less than you last criticise your work? How did it feel, and what did you do?

• Listen for: a real moment, an honest first reaction and what changed afterwards.
• Pause if: nothing comes to mind, or the critic is always wrong.

10. When were you last properly stuck? Who did you go to, and after how long?

As a cofounder, the person they go to will often be you.

• Listen for: a recent example, a named person, and a frank view on whether they waited too long.
• Pause if: they never get stuck, or never ask anyone.

11. What would former colleagues say is hard about working with you, and which areas would you lead?

• Listen for: something specific and slightly uncomfortable, plus clear areas they would own in the first year.
• Pause if: a strength dressed up as a flaw, or they want to own everything.

Where they want the company to go

12. What should this company be in five years, and what outcome would you be happy with?

Founder Institute's list asks outright whether you would sell for $5 million or hold out for $100 million.

• Listen for: a clear picture and a view on what they would accept along the way.
• Pause if: the picture shifts mid-conversation, or they won't discuss a gap with yours.

13. Do you want to raise outside money, and when?

• Listen for: a reasoned preference they would revisit once there are customers and numbers.
• Pause if: they want to raise before there is anything to show, or refuse with no reasons.

14. Which part of the idea is fixed for you, and when did you last drop an idea you cared about?

• Listen for: commitment to the problem or the customer, flexibility on the solution, and a real example of letting go.
• Pause if: attachment to one feature, or no example of ever changing course.

15. What is the biggest risk you have taken with your own money or time?

• Listen for: real stakes and a clear account of how they decided.
• Pause if: nothing that mattered was ever at risk, or every bet used someone else's money.

Conflict, values and setbacks

16. Tell me about a work conflict that got resolved, and one that never did.

The unresolved one shows where they stop trying.

• Listen for: owning their part in both.
• Pause if: the other person was entirely to blame, or there has never been a conflict.

17. When you disagree, do you get loud, go quiet or go around the person? How should we settle it?

• Listen for: an honest description of their style and a concrete rule, such as who decides in which area or a trusted person to break ties.
• Pause if: "we'll always agree", or they expect to win by default.

18. What won't you compromise on, and when was that last tested?

Adapted from Antler's 36 questions. The second half checks whether the value holds.

• Listen for: a short list with reasons, and a real moment they held the line.
• Pause if: a long list, an empty one, or no example.

19. What is the longest you kept going on something that wasn't working, and what made you stop?

Founder Institute's list treats never having failed at anything as a red flag.

• Listen for: an honest view of whether they stopped too early or too late.
• Pause if: no failure at all, or they have never stopped anything.

Proof beyond the answers

20. Who can I speak to who has worked with you, and would you do a short trial project?

Lin prototyped for about two weeks with each candidate before going further.

• Listen for: names offered quickly, and a yes to a trial with an end date.
• Pause if: nobody to name, resistance to any trial, or pressure to commit first.

Good answers earn a trial, not a commitment. For the whole process, from working out what you need to deciding, see our guide on how to find a cofounder.

Where Foundinity fits

Questions 8 to 19 are about how someone works, which no profile list or LinkedIn page shows. Foundinity moves part of that step before the first call.

You state what you need in a cofounder, and answer an assessment about how you work: commitment, working style, ambition, personality, goals, values, alongside your skills and interests. A multi-trait algorithm built on established psychological compatibility models ranks the people you see.

• A compatibility breakdown on every match shows where you align and where you differ, so you know which of these questions to start with.
• A 10-day clock on each match keeps it from sitting unanswered, and you book the intro call in the app.
• Your profile isn't public. Only compatible members can see it, and an "exploring" status lets you look before you commit.
• Free to get started: 5 likes a week, up to 3 active matches and up to 3 profile saves. Plus costs $5 a week or $15 a month (₹300 or ₹1,000 in India) and adds 15 likes a week, unlimited active matches and everyone who liked you.

FAQ

What should you ask a potential cofounder?

Ask why they want to start a company now, how many hours they can give, how they behave under pressure and in disagreement, what they want the company to become, and how long they can manage without a salary. Questions about real past events tell you more than questions about opinions.

When should you ask a potential cofounder these questions?

After a first call has shown there is a reason to keep talking, and before either of you commits. Write your answers separately, then discuss them in person over several sessions rather than in one long meeting.

How do you know if a potential cofounder is being honest?

No single question is lie-proof. Ask about specific things that happened, follow up on the details, pair questions so the flattering answer can't be given twice, speak to people who have worked with them, and run a short trial project before deciding.

Are there longer lists of cofounder questions?

Yes. First Round Review publishes a 50-question list compiled by Gloria Lin, Founder Institute has one with 34 and Antler one with 36. Some of their questions cover the stage after two people have decided to work together, which this guide leaves out.

Sources

• Ouellette and Wood (1998), "Habit and Intention in Everyday Life", Psychological Bulletin.
• First Round Review, "The Founder Dating Playbook" by Gloria Lin, and its 50-question list.
• Founder Institute, "34 Questions to Ask a Potential Co-Founder" (fi.co/insight/34-questions-to-ask-a-potential-co-founder), checked 22 October 2026.
• Antler, "36 Questions to Fall in Love with Your Co-Founder" (antler.co/blog/36-questions-to-fall-in-love-with-your-co-founder), checked 22 October 2026.