Discover more from Human Ventures
The Best Questions to Ask a Potential Co-Founder Have Nothing to Do With Work
Written by Esther Perel
There’s no “one and only” partner for your startup. But couples therapist Esther Perel will help you feel confident in the one you choose.
In one of the first sessions for my podcast, How’s Work, I sat across from two co-founders who could barely sit next to each other, let alone make eye contact. They met in college, traveled the world together, and started a company after graduation. As their startup grew over the next decade, their relationship degraded. On the surface, their fights were about profits and protocols. But when they came in for a one-time session for How’s Work, the reality of much deeper issues emerged. In fact, their conflict had very little to do with the company itself.
Underlying their frustrations and perceived transgressions lay fundamental questions about their relationship: Who cared more about the other? Who held more power? Who received recognition? Could they trust each other? I’ve seen similar dynamics play out between colleagues of all kinds—across my roles as a relationship therapist, the host of How’s Work?, and an advisor to Human Ventures. And I’m not alone in my observations: Noam Wasserman, the author of The Founder’s Dilemma, found that 65% of startups fail because of interpersonal tension within the founding team.
Why do so many co-founders develop strained relationships? It’s not necessarily the stress of the startup environment, misaligned visions, or incompatible communication styles. It’s a failure to understand the nuanced dynamics of partnership in the first place. The truth is that how we work together is about so much more than work.
The startup world’s abundance of co-founder questionnaires and data-driven matching platforms advise many people otherwise: As tools designed to help you find the “perfect partner,” they reinforce prioritizing what looks right on paper—networks, skill sets, founding experience, working styles, industry accolades, and more. But someone’s professional resume—whether it features five Webby awards or a nine-figure exit—tells you next to nothing about what it will be like to work with them every day.
This is where our “relationship résumés” come in. Along with a career history, everyone brings a layered history of professional, romantic, platonic, and familial relationships to the workplace. This relationship résumé, as I call it, informs how each of us communicates, builds trust, navigates uncertainty, manages power dynamics, and approaches conflict. And it can tell you so much more about whether you should start a company with someone than a traditional CV. When people say you should bring your whole self to work, my response is always this: You already do. It just may not be consciously.
How do you begin to learn about a potential co-founder’s relationship résumé? In my almost four decades as a therapist for pairs of all kinds, I’ve found there are seven key verbs that shape how we engage with ourselves and others: to ask, take, receive, give, acknowledge, refuse, and play. The below questions are a starter guide to understanding your experiences around each of these verbs, as well as your business partner’s. Take turns asking them and you’ll create space for profound understanding of each other’s relationship dynamics.
1. To ask
Some people know what feels meaningful to them and have no problem stating their needs. Others struggle with asking for what they want. Use these questions to reflect on each person’s comfort with asking.
Have you always known what you wanted in life?
When you’re faced with a problem, do you ask for help or are you more inclined to try to do everything on your own?
What is the hardest thing you've ever had to ask for?
2. To take
When we allow ourselves to feel deserving of time, attention, and resources, we’re able to fully engage in the moment and make the most of our ask. Use these questions to explore each person’s experience with “healthy” entitlement.
What do you do when you identify something that you think you need or deserve?
How do you experience taking up time, space, initiative, and sharing ideas?
Describe a time when you dealt with someone who hogged the mic and grabbed all the attention.
3. To receive
Receiving is not the same as taking. Receiving connects to our vulnerable parts, while taking connects us with our self-sufficient and confident parts. When we receive something, we allow another person to take care of us. Use these questions to consider how each of you receive.
How do you deal with surprises?
Tell me about the last time someone helped you. How did you feel?
Tell me about a time you asked for something important and received it. What was it? How did you feel?
4. To give
Giving can be a way to practice an abundance mindset. It can also be a way to avoid conflict and ignore your own needs. Use these questions to get curious about each person’s experience with giving.
Do you give in response to other people’s requests or do you tend to give it freely?
In times of abundance, what do you do with your resources?
What about in times of scarcity?
5. To acknowledge
Acknowledgment is a form of honesty. To acknowledge something is to sit with the truth, even when it’s uncomfortable, rather than hiding from yourself or others. Use these questions to explore each person’s relationship to truth and comfort.
Is there someone whom you feel owes you an apology? Is there someone to whom you owe an apology?
When was the last time you made a mistake? How do you acknowledge your fallibility?
Have you ever changed your mind?
6. To refuse
Without a no, we can't develop a yes. But so many of us have a complicated relationship with our own right to refuse. Use these questions to reflect on how each of you set boundaries with yourselves and others.
Have you ever ended a friendship?
Think of a time when you wanted to give up. Which part of you prevailed?
Tell me about the last time you said “no.”
7. To play
This is the verb connected to our creativity and our ability to problem solve. Play takes us beyond the bounds of reality and elicits our imagination. It gives us a frame and permission to experiment and to take risks. Ask these questions to explore each person’s experience with play.
What would you do if you had a different career?
What do you need more: security or adventure?
What is your idea of a perfect day?
There are no right or wrong answers to these questions. The point is to unearth the unseen dynamics of these seven verbs—in yourself and your partner—and explore your desire to learn to manage them together. After the conversation, ask yourself: Where did you say “Tell me more”? Where did your stomach tighten? Can you put yourself in each other's shoes, even if your answers differ?
Compatibility is not something you can simply optimize with an algorithm or a multiple-choice test. It is a dance—a unique and ever-evolving interaction—and the health of your relationship depends on your willingness to meet each other at every twist and turn. The health of your business does, too: As organizations like Human Ventures increasingly emphasize, the quality of our work ultimately depends on the quality of our relationships.
I often say there’s no “one and only”; there’s only the one you choose. Whether you’re building a business or a family, you want a partner who will bring out the best version of yourself—even in the most challenging situations.