36 Questions to Fall in Love with Your Co-Founder

Building a venture-backed startup is one of the most intense relationships you’ll ever experience. It’s not just about finding someone with complementary skills—true co-founder relationships require trust, shared vision, and a connection that can weather challenges as much as successes. In some ways, it mirrors the closeness of a personal relationship, which got me thinking about the famous "36 Questions to Fall in Love."

In the 1990s, psychologists Arthur Aron and his team developed a set of questions designed to accelerate intimacy between two people, later popularised by Mandy Len Catron in a New York Times essay. Their goal was to see if vulnerability and openness could fast-track connection. Given that building a business with a co-founder often involves a similar depth of connection, I wondered: could we adapt these questions to build a strong foundation for a co-founder relationship?

The Inspiration: 36 Questions to Fall in Love

The original 36 questions (which I’ll link to at the end of this post) are designed to peel back layers of emotional and intellectual intimacy. They start with surface-level inquiries and gradually dive deeper into personal history, values, and beliefs. By the end, two people should know each other in ways that most casual relationships never reach.

If this kind of connection is possible between strangers, could similar questions help founders create a partnership capable of building a company from scratch? I set out to adapt these questions, tailoring them to the realities of entrepreneurship and the co-founder journey.

Setting the Stage for Co-Founders

Finding time to truly connect with a potential co-founder outside the pressure of the office or pitch meetings is crucial. I recommend using these questions during a walk or some other relaxed setting where you can comfortably talk for an hour or more. The goal is to create an environment that fosters open conversation and gives each of you the space to reflect deeply on what the partnership could mean.

As you go through the questions, allow yourself to be fully present. Don't rush. This process is about discovering more than just work compatibility; it's about understanding each other's deeper motivations and long-term visions.

36 Questions to Fall in Love with Your Co-Founder

I’ve broken these questions into three sets, much like the original framework. They start by uncovering values, move into exploring personal and professional alignment, and end with questions designed to build trust and honesty.

Set I: Uncovering Aspirations and Values

1. Given the choice of any entrepreneur or leader in the world, whom would you want as a mentor for our venture?
2. Would you want to be known as a successful entrepreneur? What would success mean to you in that role?
3. Before pitching or speaking with investors, do you usually prepare in advance? Why or why not?
4. What would a “perfect” workday look like for you in our startup?
5. When was the last time you truly felt proud of your work?
6. If you could maintain either the creativity or energy of your current self for the next 60 years, which would you keep?
7. Do you have a gut feeling about what our biggest challenge as co-founders might be?
8. Name three strengths or values that you believe we share.
9. What in your professional journey do you feel most grateful for?
10. If you could change anything about your early career, what would it be?
11. Take four minutes to describe the path that led you to entrepreneurship.
12. If you could suddenly gain any one skill to help with this startup, what would it be?

Set II: Exploring Vision, Risks, and Shared Goals

1. If you could know one thing about the future of our business, what would you want to learn?
2. What’s something you’ve always wanted to try in business but haven’t? Why?
3. What’s your proudest achievement so far in your career?
4. What do you value most in a professional partnership?
5. What’s your most rewarding professional memory?
6. What’s your biggest professional challenge so far?
7. If you knew our startup would fail in one year, would you approach anything differently? Why?
8. What does professional camaraderie mean to you?
9. What role do passion and purpose play in your work life?
10. Take turns sharing something you admire about each other as co-founders. Share a total of five attributes.
11. How close are you with your professional mentors? How have they shaped your decisions?
12. How has your early professional experience influenced your work style today?

Set III: Building Trust and a Shared Vision

1. Make three true “we” statements about our venture. For example, “We both care deeply about…”
2. Complete this sentence: “I wish I had a co-founder who would…”
3. If we were going to build a truly strong partnership, what do you think I need to know about you?
4. Tell me something you respect about me as a co-founder that you might not say to anyone else.
5. Share a challenging moment from your career. How did you overcome it?
6. When was the last time you felt emotionally invested in your work?
7. Tell me something you already appreciate about working together.
8. What, if anything, is too serious to compromise on when building a startup?
9. If we had to dissolve this business tomorrow, what would you regret not having done together?
10. If you had one last opportunity to save something from our company, what would it be and why?
11. Of all the entrepreneurs you’ve worked with, whose failure impacted you the most? Why?
12. Share a current challenge you’re facing in business and ask for my advice on how to approach it. Also, reflect on how you think I’m feeling about the problem.

The Silent Reflection

In the original 36 questions experiment, participants were asked to sit in silence and look into each other’s eyes for four minutes. While this exercise might feel a little intense for potential co-founders, I’ve adapted it into a different form of silent reflection.

Strategic Reflection Exercise: At the end of your walk, spend four minutes in silence together. Look at a shared whiteboard, a pitch deck, or even visualise your startup's future. Reflect quietly on the vision you're both creating and what this venture truly means to you.

After the silence, share your thoughts: Did the silence reveal any new ideas or create alignment? What did you learn from each other in that quiet moment?

The Takeaway

Just as the 36 questions were designed to accelerate closeness between two people, these co-founder questions are meant to foster trust, transparency, and a deeper connection between potential partners. After all, the bond you build with your co-founder will likely be the backbone of your startup’s success. It’s worth investing the time to truly understand each other’s values, goals, and strengths.

Curious about the original 36 questions? You can find them here. But whether you’re falling in love or starting a company, the key is openness, vulnerability, and mutual respect.