10 Questions to Smash with Your Startup Co-Founder

Building a startup is one of the most intense professional relationships you'll ever experience. The late nights, the pivots, the celebrations, the near-death experiences—you'll go through them all with your co-founder by your side. Yet many founders spend more time on their pitch deck than on truly understanding the person they're about to spend the next decade building with. Here's a startling truth: co-founder conflict is cited as one of the top reasons startups fail. A large number of high-potential startups fail due to co-founder conflict. The relationship you build with your co-founder will be tested in ways you cannot yet imagine. So why not invest the time upfront to build a foundation strong enough to weather any storm?

The Inspiration Behind the Questions

In the 1990s, psychologist Arthur Aron developed 36 questions designed to accelerate intimacy between strangers. These questions proved that vulnerability and openness could fast-track deep human connection. If two strangers could develop profound closeness through structured conversation, couldn't potential co-founders use a similar approach to build the trust and alignment necessary for entrepreneurial success?

The answer is yes—but startup founders don't have time for 36 questions. You need something focused, powerful, and actionable. That's why we've distilled the essence of this research into 10 carefully crafted questions that cut straight to what matters most in a co-founder relationship.

Before diving into these questions, set the stage properly. Don't have this conversation in your office or over a rushed coffee between meetings. Take a walk together. Find a quiet space where you can talk uninterrupted for 90 minutes. Leave your phones behind. This isn't just another business meeting—it's an investment in the most important relationship your startup will ever have.

The key is presence. Be fully there. Listen not just to answer, but to truly understand. The magic happens in the pauses, in the moments where someone struggles to articulate something they've never said aloud before.

Now you are ready to answer the following 10 Essential Questions:

1. What Does Success Actually Mean to You?

Beyond the metrics and valuations, what would make this journey worthwhile? For some founders, it's impact. For others, it's wealth creation, creative freedom, or building a legacy. There's no wrong answer, but misalignment here can be catastrophic. Dig deep: what are you actually optimizing for?

2. How Do You Handle Failure and Disagreement?

You will fail. Repeatedly. You'll also disagree with your co-founder on critical decisions. Share a story about your biggest professional failure and how you processed it. Discuss how you approach conflict. Are you confrontational or avoidant? Do you need time to cool down or hash it out immediately? Understanding these patterns now can prevent nuclear meltdowns later.

3. What Are Your Non-Negotiables?

Every founder has lines they won't cross. Maybe it's about work-life balance, ethical boundaries, or how you treat employees. What would make you walk away from this venture? What values are so core to your identity that compromising them would make the whole journey meaningless? Get these on the table now.

4. What's Your Relationship with Money and Risk?

Be brutally honest about your financial situation and risk tolerance. Can you go a year without salary? Two years? Do you have family depending on you? Are you comfortable with debt? How do you think about personal wealth versus reinvesting in the company? Financial stress is a startup reality—make sure you understand each other's constraints and comfort zones.

5. How Do You Want to Make Decisions Together?

Will you operate by consensus or does someone have final say in specific domains? How long should you debate before acting? What's your pace—move fast and break things, or careful and methodical? Create alignment on your decision-making framework before you're in the heat of a critical choice.

6. What Scares You Most About This Journey?

Real vulnerability builds real trust. Share your actual fears—not the polished, investor-friendly version. Are you afraid of letting your family down? Worried you're not technical enough? Scared of public failure? When you know each other's vulnerabilities, you can support each other through them rather than accidentally triggering them.

7. If Everything Goes Wrong, What Do You Want to Walk Away Having Learned?

This question shifts perspective from outcome to growth. Even if the startup fails, what skills, relationships, or insights would make this time well-spent? Understanding this helps you design the journey to be valuable regardless of destination—and reveals what each person truly values.

8. What Does Our Partnership Need That I'm Not Naturally Good At?

Practice honest self-awareness. Where are your blind spots? What skills or perspectives do you hope your co-founder brings? This creates space for complementary strengths and helps each person understand their unique value in the partnership.

9. Complete This: "I Wish I Had a Co-Founder Who Would..."

This simple prompt reveals unspoken expectations. Maybe you wish for someone who'd challenge your ideas more. Or someone who'd handle all investor relations. Or someone who'd remind you to take breaks. These wishes often highlight what you value most in a working relationship.

10. What's a Challenge You're Facing Right Now, and How Can I Help?

End with action. Share something real you're struggling with—maybe it's a technical problem, a personal doubt, or a strategic question. Then listen to how your potential co-founder approaches helping you. Their response reveals their problem-solving style, empathy, and how they'll show up when times get tough.

After working through these questions, try something unconventional: sit together in silence for four minutes. You might look at your business plan, stare at a whiteboard, or simply close your eyes. Let the weight of what you've shared settle. Then discuss: what did that silence reveal? Did you feel comfortable or awkward? That feeling tells you something important about your compatibility.

At Dock Startup Lab, we believe that exceptional startups are built by exceptional teams. Our founder academy exists not just to teach business models and growth strategies, but to help you build the relationships and self-awareness that underpin sustainable success. These questions are a starting point. The founders who invest time in these conversations before signing partnership agreements consistently report stronger alignment, faster decision-making, and more resilience through challenges.

Your Next Step

If you're exploring a potential co-founder relationship, block time this week for this conversation. If you're already in partnership, these questions can help you go deeper and realign on what matters most. And if you're looking for support on your founder journey, explore how Dock Startup Lab can help you build not just a better business, but a better founding team.

Because at the end of the day, you're not just building a company but you're choosing the person you'll navigate uncertainty with, celebrate victories with, and learn hard lessons alongside. Make it count.

Ready to accelerate your founder journey?