August 22, 2024

Why You Should Ask 50 Questions Before Choosing a Co-Founder

Choosing a co-founder is one of the most critical decisions you'll make when starting a company.

The relationship between co-founders can significantly impact the success or failure of a startup.

To ensure compatibility and alignment in your partnership, it’s crucial to ask the right questions early on.

This comprehensive guide presents 50 questions, divided into six key categories, designed to spark deep conversations that will help you and your co-founder build a strong foundation for your business partnership.

How You Operate

Understanding each other’s strengths, weaknesses, and work styles is crucial for a successful partnership.

This category focuses on how you and your potential co-founder approach work and challenges.

Here are the questions to explore:

  1. What are your strengths and superpowers (beyond functional expertise)?
  2. What are your weaknesses? How do you try to compensate for them?
  3. What words would your co-workers use to describe you? What would they want me to know about what it’s like to work with you?
  4. How do you deal with conflict? Describe a time you dealt with it well — and a time you didn’t.
  5. What’s the worst interpersonal conflict you’ve dealt with? How did you handle it?
  6. How do you cope with stress? Depression? Are there any red flags I can help watch out for?
  7. How do you arrive at your convictions? What are some key mental models you use to be creative, solve problems, or make decisions?
  8. Describe your work style. What techniques do you use for personal productivity?
  9. How many hours per week are you willing to work? For how long? What sounds good? What sounds like hell? Do you have different expectations for different phases of the company’s lifespan (i.e., willing to work harder in the beginning)?

Roles

Defining roles early on can prevent confusion and conflict later.

This category helps you and your co-founder understand your expectations for each other's roles and responsibilities within the company.

Key questions include:

  1. What would you want your role to be before we reach product/market fit? What would you want your role to be after we reach product/market fit?
  2. How do you see your role changing as the company starts to scale?
  3. If your role becomes unavailable entirely (e.g., the board hires a professional CEO or an experienced executive), what would you want your new role to be?
  4. Areas of Responsibility (AoR) Exercise: Rank yourself in these areas (both as an individual contributor and as a leader) on a scale of 1-10. Then rate your passion in each of the above areas on a scale of none to high. (e.g., “I’m an 8 in sales, but hate it so none”):
  • Sales
  • Marketing
  • Product Strategy
  • Design
  • Engineering
  • Operations
  • Fundraising
  • Leadership
  • Company Building
  • Recruiting
  • Legal
  • Specific Skills (e.g., Healthcare, Machine Learning, etc.)
  1. Cluster AoRs based on rank and discuss how they could be assigned to individuals. (E.g., John is a 10 in product, so he gets that AoR).
  2. Break ties using the passion rating. (E.g., Nick is a 7 in sales with medium passion, and Gloria is a 7 in sales with high passion, so Gloria will take on sales).
  3. Discuss: Do these clusters align with everyone’s expectations, skills, and desires? Do we all agree on the areas of responsibility for the CEO, CTO, COO, etc.?

Corporate Structure and Funding

This section prompts discussions on critical topics like equity distribution, funding philosophy, and exit strategies.

It ensures that you and your co-founder are aligned on how to build and finance the company.

Consider these questions:

  1. Where should our startup be based? How do you feel about remote or distributed teams?
  2. Is there anything I should know that may materially affect your time or legal status as a founder? (e.g., visa, green card, criminal record)
  3. How should founder equity be set? What’s your philosophy on the employee equity pool?
  4. What should our approach to employee compensation be, including cash and equity?
  5. How much money should we raise? (i.e., “zero” to “as much as we can”) In the range of “bootstrapped small business” to “go big or go home,” where do you want this startup to go?
  6. What matters most in a funder? If you were doing reference checks on a VC or potential board member, what traits would you be looking for?
  7. What does an ideal company exit look like to you? (i.e., “work on company for 1-2 years and sell for 7 figures” to “work for 10+ years, reach 9 figures in revenue, and IPO”)
  8. How do you think about the timeframe and pace of success? Are you willing to take the longer path? How long is too long?
  9. What number would you sell at? How would that change if you got extra liquidity from your existing positions?
  10. What do we do if we find product/market fit, yet none of the founders are excited about that product?
  11. Can one co-founder fire another co-founder? Can someone else fire a founder?

Personal Motivation

Understanding each other's motivations can help align your goals and ensure that you're working towards a common vision.

This category delves into what drives you and your co-founder.

Discuss the following:

  1. Why do you want to start a company — in general, and in particular right now?
  2. What is success to you? What motivates you personally?
  3. What impact do you want to have? Is your startup objective “getting rich” or “changing the world”? Is control or success more important? (i.e., Are you willing to step aside if the company is more likely to have a financially successful outcome, or is it important for the founders to stay in control of the company’s destiny?)
  4. What makes you gritty?
  5. Who do you admire most in your organization, family, or friends, and why?
  6. What are you most proud of in your work career or life to date?
  7. When have you taken a chance when others did not? Or when have you been willing to take an unpopular stance?
  8. What are some of the products and companies you love, and why?
  9. Is it possible to build a wildly successful company without burning out or damaging other parts of your life (family, health, etc.)?

Commitment and Finances

Clarify your commitment levels and financial expectations to avoid misunderstandings later.

This section ensures that you and your co-founder are on the same page regarding the time and financial investments required.

Consider asking:

  1. Will this company be your primary activity? Do you have any other time commitments?
  2. What is your expected time commitment right now? How do you see that changing in the next 6 months? 2 years?
  3. What is your personal runway? Current burn rate? Would you invest your own money (ideally retaining higher equity in return)?
  4. What is the minimum monthly salary you need to survive? To be comfortable? To feel like you’ve “made it”?
  5. What should the policy of co-founders advising/consulting with other companies be?

Team Culture and Co-Founder Relationship

Finally, it's essential to discuss how you envision your company's culture and how you will manage your co-founder relationship.

These questions help you align your expectations for the company's environment and your partnership.

Key questions include:

  1. Complete the sentence: It would make you proud to hear people describe this company’s culture as _________. (Values are written words, and your culture is how you actually live those written words.)
  2. What’s your philosophy on how to attract and retain great people? Tactically, how would we make this happen at our company?
  3. What processes or techniques would you use to get the most out of your team? For example, how would you help them become better managers or achieve their goals?
  4. How much of your time do you hope to spend either working or socializing with coworkers?
  5. How important is diversity and inclusion? Concretely, how would you put that into action?
  6. Specifically, how are we going to prioritize and make time for our co-founder relationship as we get increasingly busy with company building?
  7. How would we resolve personal conflict between ourselves? How about stalemates?
  8. In case this becomes part of our partnership’s evolution, how would you go about handling a startup divorce?
  9. Wrap-up question: Now we know each other’s weaknesses, passions, needs, and constraints––how are we going to make each other successful? What would it take to feel truly partnered in this adventure?

Conclusion: Building a Strong Foundation

Choosing the right co-founder requires more than just finding someone with complementary skills.

It’s about ensuring that you share the same vision, values, and work ethic.

By asking these 50 questions, you can gain a deeper understanding of your potential co-founder’s motivations, expectations, and approach to business.

These conversations will help you build a strong foundation for a successful partnership, increasing your chances of building a thriving company together.

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