50 Questions to Explore with a Potential Cofounder

 

To organize my thoughts about startup and co-founders, I wrote down this document. This template is from First Round Review.

This document will be updated, whenever my thoughts change.

PART 0: HOW YOU OPERATE

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

I easily identify potential improvements for products or systems. Also, my performance remains unaffected by stress. Many people around me have mentioned that I seem like a stress-free person. Additionally, I have great resilience.

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

When there is no visible evidence of achievement or progress, my confidence decreases. To overcome this, I set specific objectives, minimum trying periods, and task completion conditions before starting anything.

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?

They would describe me as someone who lives life like playing a game. I am good at defining our challenges, determining what we need to do immediately, and how to tackle it.

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

Conflict usually occurs in two conditions:

  • When the grounds of the arguments are abstract or there is a lack of understanding between people’s ideas.
  • When all ideas make sense, but there is no decision maker.

In the first case, I insist on concrete reasons and request the same from the opponents. If it’s hard to explain verbally, I use drawings. In the second case, we choose a king of the task who takes complete control.

As a PM at a startup, there was a conflict between the designer, the operations team leader, and me about product creation. We drew our ideas on a whiteboard and explained them in detail, similar to a design sprint. This helped us understand each other’s ideas and resolve the conflict.

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

I rarely experience conflict because people around me kindly understand my thoughts, and I am open to be convinced. However, breaking up with my girlfriend was particularly challenging. We didn’t have a time buffer to alleviate the blow of the breakup, and my stance was not assertive. So the things that I learned from that experience, set some time buffer and be assertive.

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

Drawing from my experiences, Stress is alleviated only when its cause is resolved. I try to deal with stressors as soon as possible. For my daily stress, I listen to music loudly. When I am extremely stressed, I lose my appetite and skip meals. This is a red flag.

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

I always focus on “why.” Starting with why and ending with why. I repeatedly question why something should work in a certain way or why I need to do it.

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

I prefer a maker’s schedule, working for two or three hours consecutively, then taking breaks such as walking or reading books. Also, in order to decrease my impulsive behaviors, I practice dopamine fasting.

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)

I don’t mind the number of working hours. I rest when I need new stimuli.

PART 1: 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?

Before reaching product/market fit, my role would be project owner, handling everything related to product development, including user interviews, planning, and programming. After reaching PMF, I will focus on developing the product and improving the company’s throughput.

11. How do you see your role changing as the company starts to scale?

I will focus more on improving the company’s throughput and developing strategies.

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?

I would want to develop new products.

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”):

I have passion in these areas: PRODUCT, STRATEGY, ENGINEERING, LEADERSHIP

PART 2: CORPORATE STRUCTURE AND FUNDING

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

I am not fond of remote or distributed teams. In early stage startup, the bonds and communication between members are super important.

TBD

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

TBD

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

Equity! Always have skin in the game. First 10 employees are the foundation of the company because they’ll bring the next 100 employees and create culture. To surround yourself with the best people and unleash their potential, we need to give them 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?

Preferably bootstrapped for as long as possible. Only raise funds if there is a clear opportunity for rapid growth and a plan to use the money effectively.

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?

Tenacity and obsessiveness. I’ll check mainly one thing: Can they get things done?

20. What does an ideal company exit look like to you? (i.e., “work on the company for 1-2 years and sell for 7 figures” to “work for 10 years, reach 9 figures in revenue, and IPO”)

Work for 8 years and sell for 9 figures.

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?

TBD

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

I will sell a small portion after each funding round. Extra liquidity helps me focus on bigger goals without worrying about daily annoyances.

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

Once product/market fit is found, the product’s growth becomes the primary motivator, even if the initial excitement fades.

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

If a co-founder becomes detrimental to the company, they can be fired, even if they are a founder.

PART 3: PERSONAL MOTIVATION

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

Developing a great product that people love makes me happy. I am most immersed when creating products. As I get older, the risks increase. There are limited opportunities to take on such risks, and now is the best time.

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

Improving people’s lives is what success means to me.

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?)

Changing the world is my goal. I want to stay in control of the company’s destiny. Once I have more money than necessary, control matters more than additional wealth.

28. What makes you gritty?

The feeling of making progress.

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

My role model is John Kim, CEO of Sendbird. He can organize abstract ideas into concrete plans and has the tenacity to achieve his goals. I’ve learned a lot from his YouTube videos.

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

I created a service that customers and colleagues use to manage configurations for offline space analysis. As a PM and developer, I saw it grow from a few users to almost every customers using. I’m proud of the lean process we used to develop it.

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

When I know what others don’t know and the risk is worth taking.

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

I love Notion, GoodNotes, YouTube, and Karrot Market. They are integrated into my daily life and help me live smarter. I can study more efficiently using Notion and GoodNotes. I can learn a lot from YouTube, and I can save money and recycle products through Karrot Market. I want to create products like these

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

Starting a startup will change my life significantly. It’s inevitable to give up some aspects of life.

PART 4: COMMITMENT & FINANCES

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

Yes, the company will be my primary activity. Family and health are the next things I care about.

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

I will commit as much time as needed.

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

I have a 6-month runway. I would invest my own money for higher equity.

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

At least $2000 per month.

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

TBD

PART 5: 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.)

Tenacity.

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

Attract and retain people the same way as investors. Show them our vision and growth, and explain how they can contribute. Being a good person to work with is crucial.

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?

Provide sufficient resources and actively teach them about our company.

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

Most of my time. I enjoy working and socializing with coworkers.

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

The most important factors are intelligence and the ability to get things done. An atmosphere that encourages taking risks and learning from failure is essential. This can be achieved through company’s principles like “give it a try with a good plan, get it done, and if it fails, share the experience with coworkers.”

PART 6: 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?

We should align the company’s vision and next steps with co-founders. Periodic one-on-one meetings with co-founders are necessary.

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

By having open and frequent communication with co-founders.

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

TBD

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?

TBD

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?

Hire someone who can compensate for my weaknesses. If the weakness can’t be replaced by others, it may become a problem.

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

Two or three co-founders are ideal. In an early-stage startup, this helps us develop the product quickly.

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?

TBD