Delve In-sights

20 Questions Co-Founders Should Ask Each Other (that don’t have yes/no answers)

Co-founder relationship challenges can often be traced back to insufficient due diligence at the outset about each other’s dreams, skills, interests, and motivations. Here are 20 Questions to frame up these discussions that all founders should answer.

Why and how

  1. Why do you want to join or build a startup (in general and in particular, right now)?  (see Simon Sinek’s video)
  2. What work motivates you (e.g. technical challenges, solving problems, setting strategy, managing people)?
  3. How much time are you willing to give?  Is this likely to stay stable or change?
  4. How will the work on this fit within your other priorities? 
  5. How do you want to be compensated?  How should we divide up equity?
  6. What would keep you from being able to honor your commitments to this work?
  7. What would a good exit look like for the company, from your perspective?
  8. What if you want to leave or change your relationship to the organization and me? 

Roles and relationships

  1. Who will do what?  What do is your best contribution to this organization’s success? 
  2. What do you love to do?  What do you hate to do?
  3. How will decisions get made?  How do we break ties?
  4. Why would we be good working together?
  5. How do you handle conflict?  Give feedback?
  6. Describe your leadership style.  Impact of our different styles?

Organization and funding

  1. What do you want to build?  How big do you want it to be?
  2. In what order do we think we should add staff?  Key roles?
  3. Management structure as we scale – what could this look like?  Who does what?
  4. What culture do you want – top 3 words to describe it?
  5. What role do you want to play in raising capital?
  6. Who will be the primary interface with our Advisory Board or Board of Directors?

This is not an exhaustive list and you can’t answer these once and assume you are in good shape in perpetuity.  People’s needs, interests, and personal situations change.  Good co-founder relationships are based on trust and open, continuous communication.  If you find yourselves struggling in any of these areas, seek help early, before unhealthy patterns take root. 


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