Part 0: How You Operate

  1. What are your strengths and superpowers (beyond functional expertise)?
  2. What are your weaknesses? How do you 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/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)

Part I: Roles

  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? (Read this article giving away your Legos.)
  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”):

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