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Adapting Proust to narrower pursuits

Disclaimer: I wrote the following for my own use and while in all things startup I have a mild allergy to the heavy pontification, self-aggrandizement and disingenuous emulation out there, I thought I’d publish this in case it’s of use to someone else.

Like doing the YC application early on in a project to see whether you can articulate your plans such as they live in your head (and keep an honest account of your thinking over time), writing down assumptions about your partnership can help uncover important topics: I propose an amended questionnaire.

Many have already written about founder traits and the importance of choosing the right partner in the early days of a project. The ramifications of this choice are hardly overstated. From experience I can attest to the importance of finding a partner who will — beyond providing insight and expertise in the field of choice — provide enthusiasm, levity, respect, and that extra spark (maybe mutual admiration?) that makes working with a very special teammate something you wake up excited to do.

Providing a guide to recognizing that chemistry with another seems an arduous task best left to trying out the partnership itself. However, beyond this rapport, I think a couple other factors should be considered before getting in bed with someone and giving them control over your fate, as co-parent to your intellectual child.

Namely these are:

  • Ensuring you are aligned with regards to the kind of project (dare I say business) you want to build,
  • Ensuring you are aligned with regards to your egos (that is your visions of yourselves).

Building something from scratch is an intensely personal thing, and with it comes moments of painful, intense vulnerability and failure. The flip side of the control you have over the project is the fact that your character will not be tampered by an existing culture, and your sense of self (all of it) gets tied up into this project, which is especially painful when it comes to your shortcomings. This can mean getting blinded by ego and interpersonal doubts, rather than remaining focused on execution.

While you will no doubt improve and grow in many respects, for the most part you’re stuck with yourself (warts and all). Best have an honest conversation about it with your co-founder-to-be so you can gauge whether these traits are likely to cause meaningful friction in your day-to-day.

To that end, here is a questionnaire for sussing out potential issues that might arise, and forcing questions you may or may not have asked one another, in the hopes they spark a conversation. There are no right or wrong answers but obviously, this is a useless exercise if you don’t take a second to answer as who you are, rather than who you wish you were.

Personality

1. What is your favorite character trait/pattern of behavior in yourself?

2. What is your favorite character trait/pattern of behavior in the other?

3. What little things can’t you let go of (pet peeves)?

4. What do you fear the most about your own behavior?

5. What do you fear most about your partner?

6. From 1-to-10, what degree of work-life separation do you want (1=my partner is my family, 10=I have airtight boundaries)?

7. On a scale of 1-to-10, how heavily do you take/give blame? Are you manic about self-improvement and self-criticism or happy-go-lucky and prompt to let the little things go?

Goals

8. Are you optimizing for control, impact, financial success, glory, etc?

9. How long are you willing to work on this if nobody cares (X weeks, months, years)?

10. How quickly do you need to see revenue?

11. What kind of success do you want for the project, and what kind would you forego (i.e. risk taking the ship down) in order to achieve it?

12. How far out in its progression do you have to look before getting really excited about what the project might become?

13. How long can you keep committing to this project if you realize it won’t become what you hoped?

Commitment

14. Is there any large risk you’re taking by doing this that your partner should know about (professional, financial, personal, etc.)?

15. Is one of you more committed to this than the other? Why?

Roles

16. What is something you’d like to do in your role?

17. What is something you should be doing in your role?

18. What is something you’d like not to do in your role?

19. What is something you should not be doing in your role?

20. What are unspoken conditions to your involvement (Any sine qua none conditions you haven’t explicited)?

21. Do you need to be talking to investors?

22. Do you need to be a public face to the project?

23. What specific day-to-day actions do you need your partner to consult you on?

24. Does your partner have any blind spots about their own skill set? What are they?

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