Co-Founder Dating Questionnaire

[dachary]

A useful checklist to prepare for a discussion with a potential co-founder. A number of questions are not applicable to an organization like a horizontal cooperative and may be marked N/A.

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

10. 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?

11. How do you see your role changing as the company starts to scale? (Read this article giving away your Legos.)

12. 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?

13. 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^

^ Domain or technology-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?

Part II. Corporate Structure and Funding

14. Where should our startup be based? How do you feel about remote or distributed teams?

15. Is there anything I should know that may affect materially affect your time or legal status as a founder? (e.g. visa, green card, criminal record)

16. How should founder equity be set? What’s your philosophy on the employee equity pool?

17. What should our approach to employee compensation be, including cash and equity?

18. 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?

19. 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?

20. 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”)

21. How do you think about the timeframe and pace of success? Are you willing to take the longer path? How long is too long?

22. What number would you sell at? How would that change if you got extra liquidity from your existing positions?

23. What do we do if we find product/market fit, yet none of the founders are excited about that product?

24. Can one co-founder fire another co-founder? Can someone else fire a founder?

Part III. Personal Motivation

25. Why do you want to start a company — in general, and in particular right now?

26. What is success to you? What motivates you personally?

27. 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?)

28. What makes you gritty?

29. Who do you admire most in your organization/family/friends and why?

30. What are you most proud of in your work career or life to date?

31. When have you taken a chance when others did not? Or when have you been willing to take an unpopular stance?

32. What are some of the products and companies you love, and why?

33. Is it possible to build a wildly successful company without burning out or damaging other parts of your life (family, health, etc.)?

Part IV. Commitment & Finances

34. Will this company be your primary activity? Do you have any other time commitments?

35. What is your expected time commitment right now? How do you see that changing in the next 6 months? 2 years?

36. What is your personal runway? Current burn rate? Would you invest your own money (ideally retaining higher equity in return)?

37. What is the minimum monthly salary you need to survive? To be comfortable? To feel like you’ve “made it?”

38. What should the policy of co-founders advising/consulting with other companies be?

Part V. Team Culture

39. 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.)

40. What’s your philosophy on how to attract and retain great people? Tactically, how would we make this happen at our company?

41. 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?

42. How much of your time do you hope to spend either working or socializing with coworkers?

43. How important is diversity & inclusion? Concretely, how would you put that into action?

Part VI. Co-Founder Relationship

44. Specifically, how are we going to prioritize and make time for our co-founder relationship as we get increasingly busy with company building?

45. How would we resolve personal conflict between ourselves? How about stalemates?

46. In case this becomes part of our partnership’s evolution, how would you go about handling a startup divorce?

47. What happens in the scenario where we aren’t growing? How would we diagnose the problem? How have each of our capabilities and approach contributed to growth failures in our pasts?

48. In every partnership, there are times when a partner might breed resentment if certain dissatisfactions don’t change over time. How would you deal with a situation like this?

49. How would you think about bringing on a third (or N+1) cofounder?

50. 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?

Co-Founder Dating Questionnaire.odt (96.8 KB)

[dachary]

My answers.

Part 0: How You Operate

1. What are your strengths and superpowers (beyond functional expertise)?

   I finish what I started. I build for the long term. I’m reliable.

2. What are your weaknesses? How do you compensate for them?

   I have to remind myself that what I want is 99% of the time not what other people want. As a developer I do user research. In person I tell people what I think they want and ask them to adjust.

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?

   Focused, committed, talkative, good listener.
   I suppose people would say, on the negative, that it is sometime difficult to follow where I’m going. On the positive they said that I get things done and can be relied on to deliver.

4. How do you deal with conflict? Describe a time you dealt with it well — and a time you didn’t.

   I discuss to make sure there is no misunderstanding. If there indeed is a conflict I do my best to find a compromise. If I can’t, I leave.
   Good example: in a large community plagued by a troll, I spent around three weeks full time over six months establishing a moderation team, running it and banishing the troll. Each step was met with the approval of the community, there was no pushback.
   Bad example: a member of a non profit failed to fulfill their obligations. I publicly asked them to resign their position before engaging with a dialog with them. I later apologized and felt bad for putting them on the spot.

5. What’s the worst interpersonal conflict you’ve dealt with? How did you handle it?

   That was decades ago and with a family member. I’ve since decided to avoid work relationships with friends and family.

6. How do you cope with stress? Depression? Are there any red flags I can help watch out for?

   I avoid stress by planning ahead and not over committing so that I always have plenty of time to deal with the unexpected. I’ve never been depressed but I have good and bad days. Mostly good and I’m generally easily happy with my life.

7. How do you arrive at your convictions? What are some key mental models you use to be creative, solve problems, or make decisions?

   It’s a process that I could not describe other than it is slow. It took me around 15 years to fully understand Free Software. To be creative or solve problems I have to be immersed in the topic, during hours if not days. My decisions are based on logic. If I can’t figure out a rational way to come to a decision, I’ll do research which can take a long time.

8. Describe your work style. What techniques do you use for personal productivity?

   I maintain a list of task that need to be done on a daily basis. I start with the small things and the rest of the day is for the things that require more focus like writing code. I have a strict zero inbox policy.

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)

   40 hours/week for five years sounds good. 80 hours/week is hell. I expect the occasional bursts of activity but I don’t expect to work more than 40h/week over extended periods of time, ever.

Part I: Roles

10. 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?

    Software Developer at all times.

11. How do you see your role changing as the company starts to scale? (Read this article giving away your Legos.)

    N/A

12. 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?

    N/A

13. 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^

^ Domain or technology-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?

• Engineering: 10
• Fundraising: 5
• Operations: 5
• Recruiting: 5
• Leadership: 5
• Legal: 5

Part II. Corporate Structure and Funding

14. Where should our startup be based? How do you feel about remote or distributed teams?

    Remote only.

15. Is there anything I should know that may affect materially affect your time or legal status as a founder? (e.g. visa, green card, criminal record)

    N/A

16. How should founder equity be set? What’s your philosophy on the employee equity pool?

    N/A

17. What should our approach to employee compensation be, including cash and equity?

    The organization does not have stocks, there only are salaries.

18. 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?

    bootstrapped small business
    no money is raised

19. 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?

    N/A because there won’t be a VC

20. 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”)

    N/A

21. How do you think about the timeframe and pace of success? Are you willing to take the longer path? How long is too long?

    one year to pay the salaries of three full time employees
    two years may be possible but more than that would mean something is very wrong overall

22. What number would you sell at? How would that change if you got extra liquidity from your existing positions?

    the organization is owned by the employees and if they collectively decide to sell, they will also collectively set a price: this is not for me alone to say

23. What do we do if we find product/market fit, yet none of the founders are excited about that product?

    give up

24. Can one co-founder fire another co-founder? Can someone else fire a founder?

    the employees collectively decide that

Part III. Personal Motivation

25. Why do you want to start a company — in general, and in particular right now?

    • because no other organization will support the project
    • to set an example that others can follow

26. What is success to you? What motivates you personally?

    • the service is well maintained
    • other companies are created with the same core values to work and are competitors

    I’m motivated to create a sustainable services I can use daily to work with Free Software projects around the world.

27. 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?)

    Success in changing the world is the most important. The impact will be the disappearance of centralized forges in favor of federated forges.

28. What makes you gritty?

    Having the solution to a problem and the means to implement it. Which Hostea is: a solution for software developers to own their tools.

29. Who do you admire most in your organization/family/friends and why?

    Sage Weil because he is kind and smart.

30. What are you most proud of in your work career or life to date?

    I’m proud to have exclusively worked on making Free Software since the mid 90’.

31. When have you taken a chance when others did not? Or when have you been willing to take an unpopular stance?

    I worked and bootstrapped a company on poker software during seven years. It was the only one to be Free Software.

32. What are some of the products and companies you love, and why?

    Emacs because it has been with me since the mid 80’
    I do no love any company but I much prefer cooperatives in general

33. Is it possible to build a wildly successful company without burning out or damaging other parts of your life (family, health, etc.)?

    I’m not interested in building a wildly successful company. A successful company that inspires copy cats is more than enough.

Part IV. Commitment & Finances

34. Will this company be your primary activity? Do you have any other time commitments?

    Yes. No.

35. What is your expected time commitment right now? How do you see that changing in the next 6 months? 2 years?

    40h/week at all times.

36. What is your personal runway? Current burn rate? Would you invest your own money (ideally retaining higher equity in return)?

    My personal runway is until december 2023, burn rate is 6,000€ / month. I obtained funding for me personally.

37. What is the minimum monthly salary you need to survive? To be comfortable? To feel like you’ve “made it?”

    Survive 4,000€
    Comfortable 6,000€

38. What should the policy of co-founders advising/consulting with other companies be?

    N/A

Part V. Team Culture

39. 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.)

    Inclusive and transparent

40. What’s your philosophy on how to attract and retain great people? Tactically, how would we make this happen at our company?

    I really have no clue.

41. 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?

    Individual cells of at most 10 people using Agile. Inter cell interactions are based on the usual best practices in Free Software.

42. How much of your time do you hope to spend either working or socializing with coworkers?

There is a 10 to 20% time overhead to maintain good relationships with coworkers in the company or in the Free Software community alike. Being transparent means there really is no difference between coworkers and members of the Free Software community when it comes to social interactions.

43. How important is diversity & inclusion? Concretely, how would you put that into action?

    5% of the time is dedicated to improving diversity & inclusion

Part VI. Co-Founder Relationship

44. Specifically, how are we going to prioritize and make time for our co-founder relationship as we get increasingly busy with company building?

45. How would we resolve personal conflict between ourselves? How about stalemates?

46. In case this becomes part of our partnership’s evolution, how would you go about handling a startup divorce?

47. What happens in the scenario where we aren’t growing? How would we diagnose the problem? How have each of our capabilities and approach contributed to growth failures in our pasts?

48. In every partnership, there are times when a partner might breed resentment if certain dissatisfactions don’t change over time. How would you deal with a situation like this?

49. How would you think about bringing on a third (or N+1) cofounder?

50. 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?