How To Find a Cofounder: Ask These 20 Revealing Questions
These psychological questions will help you better understand each other and better determine goodness of fit
Since we’re a few short years away from a sleek cofounder dating app, one of the best ways to find your cofounder is to have an old-fashioned interview.
Your interview doesn’t need to be stale.
The awkwardness accompanying most job interviews is often due to the candidate’s desperation, the company’s interviewing incompetence, or other factors contributing to a one-sided engagement. But just as great interviewers ensure that it’s a two-way process, cofounders seeking to find the right match need mutual investment to ensure their working relationship will withstand the pressures of building a startup.
It’s no secret that most cofounder relationships deteriorate under near-constant distress, as 65 percent of startups that fail due to cofounder fallout. That’s why finding a good match and engaging in cofounder therapy or coaching is paramount: Your foundation must be rock-solid to achieve your goals.
The twenty questions below can help guide your initial conversations. While these are not the only questions you may need to ask one another, they are a great starting point that can help you better understand each other’s general characteristics.
Think of these questions as the first round of your interview process.
If you’re not aligned on these questions or if the person’s style of responding doesn’t mesh with your personality, use all of that as data to say “no” now.
There’s no need to waste time on more technical questions if these don’t go well.
If some of the questions feel robotic, reword them to fit your needs.
Take turns answering the prompts together and openly discuss areas where you disagree with one another. Disagreement is great! It can build a positive tension that contributes to unique problem-solving.
But if the two of you are not able to work through that tension in a positive manner, that’s an ominous sign: How the two of you address conflict and make decisions determines the ceiling of your partnership.
Ask these 20 questions to better understand the values, personality, and character of your potential cofounder:
1. Which frustrates you more: Product problems or people problems (and why)?
This question reveals a lot about your personality.
Like most questions on this list, there is no “right or wrong” answer — it’s much more about how the question is approached.
Don’t listen for the outcome of their decision, listen to the logic of how they arrive at their answer.
2. What are your most significant challenges when working in or building a startup?
What you’re looking for here is basic self-awareness.
Does this person have the ability to 1) identify and 2) discuss their vulnerabilities?
If they present as infallible, that’s a giant red flag.
3. What do you do when you’re exhausted, swamped with work tasks, and have 50 emails in your inbox?
This question helps you understand the other person’s time management strategies.
Do they leap headfirst into tasks?
Do they pause to organize a plan of action?
Do they do easy tasks before more difficult ones?
Do they think about their longevity?
Listen for a strategy that complements your own, since this scenario will happen often.
4. What support system — friends and family — keep you afloat during difficult times?
Entrepreneurship elicits existential isolation unlike most other jobs.
To combat that feeling of being completely alone, you and your cofounder need a support system.
Any positive interactions will boost resilience when it’s needed most.
5. What interests, hobbies, and passions do you have outside of work?
This question reveals layers of the person’s psychology. Listen for themes, breadth of interests, and common ground.
Does this person have activities that can help them withstand the stress of building a company?
Do they have passions that can re-energize them when they’re depleted?
Do you find yourself interested to hear more?
Trust your gut.
6. If you could have pursued a different career, what would it be and why?
Another classic personality question.
This reveals goals, desires, values, and alternative modes of thinking that fit their personality.
7. What’s the most impactful insight you’ve discovered?
Wide-open question.
They could stick to productivity hacks, share a Naval quote, discuss psychology or spirituality, or tell you an intimate story about a lesson they learned through experience.
Again, no right or wrong answer. But how they answer is quite telling.
8. How do you deal with adversity and uncertainty?
Keep in mind, this is an ego-based question.
Instead of assuming this is how they actually respond, think about more as a blend of how they respond and how they wish they’d respond.
Listen for the challenges they may choose to share. Take note, those barely acknowledged habits are likely more significant than they’re letting on. And look for someone who can be honest rather than full of fluff.
Exclusively positive answer = red flag.
9. Tell me about a time you felt rejected and how you dealt with it.
This questions pokes at vulnerability.
Look for honesty and learning from past experience.
10. What fuels you to be great?
Again, ego-based question.
Truth is, most people are fueled by compensation, but that’s the psychologist in me.
Listen for relatability — can you both connect on your motivators?
11. When things go wrong, do you blame others or blame yourself?
I like to see someone discuss the significance of context when answering this question.
And this is a layup for personal accountability. Big problem if they miss it.
12. After a conflict, do you forget and forgive or keep a running tab?
Honesty is great, because most people have a little of both in them. But the question aims at agreeableness — can they let stuff go and move on?
13. What’s a conversation you wish you had with your parents?
This questions keeps things interesting!
Informs you about regret, resentment, and what types of connections they may long for.
14. Do you prefer time alone or with others to re-charge?
If they prefer to recharge alone, they lean introversive.
If they want to go out with friends to recharge, they’re extraverted.
15. How would you describe the pressure you feel from your family?
Here, you’re looking to understand how they were shaped by their parents.
Pressure is an emotional experience. Where it impacts the individual — achievement, caretaking, loyalty, etc. — helps you understand their unspoken motivation.
16. Where do you fall on the risk-safety spectrum and why?
Tells you about how they think about risk/reward.
Also points to how they may want to work / the type of exit they may seek.
17. Do you value collaborating across multiple verticals or staying in your lane?
Discuss this early and often.
This is one that, to work well together, you must figure out before getting started.
Otherwise it’s a conflict ready to happen.
18. Are you an external or internal processor?
Helpful to discuss: Lone wolf or chatty Kathy?
It’s okay if you’re not a match here. But if you’re not, you need a plan to address moments when one person wants space and the other wants to talk it through.
19. Rate these 5 values from most to least important: [insert here]
This is blank for a reason!
Pick two or three of your top values and list them in the blank, adding a couple more that are nowhere near important for you.
One example may be: Fame, growth, innovation, wealth, mastery. In this example, I care about mastery, growth, innovation, wealth, and fame, in that order. See how they rank your values!
Look for overlap, discuss where you don’t align.
20. Tell me about a time you received negative feedback and how you handled it.
This is similar to the rejection question, but focuses on negative feedback.
You’re looking for self-awareness: Can they pinpoint traits and characteristics that can be overbearing? Are they able to use feedback in a constructive manner?
These are all important for you to know about your potential cofounder.
Finding a cofounder that matches your personality, values, and aspirations is difficult.
Take the time now instead of regretting it later. Sit down and engage in a meaningful conversation to learn more about how your characteristics fit with one another.
And if things go well, move on to round two.