startup

50 Essential Questions to Explore with a Potential Co-Founder

My answers to 50 Questions for Interviewing a Potential Co-Founder (Lin)…

Part 0: How You Operate

  1. What are your strengths and superpowers beyond functional expertise?
    Answer: My strengths lie in AWS, data engineering, system automation, DevOps and software development with Python, finding innovative solutions to complex problems and technical project management.

  2. What are your weaknesses? How do you compensate for them?
    Answer: I sometimes find it challenging to stay motivated. Setting clear goals and deadlines, helps as well as staying in contact with my team members. I also take on too much, I run a small Right to manage company, am a private landlord, have a video game I am trying to make, want to start a company, like to do volenteer work and also am a freelance AWS engineer by day. This is one of my main motivators for finding a co-founder.

  3. What words would your co-workers use to describe you?
    Answer: I tend to shy away from answering this question directly, my LinkedIn recommendations give a more accurate picture of how I’m perceived by my colleagues. You can read them for yourself here: LinkedIn Recommendations

  4. How do you deal with conflict?
    Answer: I approach conflict by listening actively to all perspectives, with the goal of trying to find a solution that benefits the team as a whole.

  5. What’s the worst interpersonal conflict you’ve dealt with? How did you handle it?
    Answer: I fell out with a family member over the management of a property we were letting on AirBNB. It got so bad that I left my flat in Barcelona and moved back to the UK so we could repair the relationship.

  6. How do you cope with stress? Depression? Are there any red flags I can help watch out for?
    Answer: I manage stress through regular exercise. For depression, I find that keeping a close circle of supportive people and engaging in hobbies like music helps. Red flags for me include working excessively without breaks and becoming unusually withdrawn. In such cases, a reminder to take some downtime is often helpful.

  7. How do you arrive at your convictions? What are some key mental models you use to be creative, solve problems, or make decisions?
    Answer: I like to research problems, looking for how others have solved them, researching papers, online, podcasts, whitepapers, blogs etc. using mental models like first-principles thinking to break down complex issues into simpler components.

  8. Describe your work style. What techniques do you use for personal productivity?
    Answer: I prefer using project management tools like Jira and generative AI to enhance productivity. My work style is organized and results-oriented, with a focus on automating processes wherever possible and leveraging technology to streamline tasks. I value efficiency, communication, and collaboration.

  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)
    Answer: I’m ready to dedicate 20 hours per week during the initial stages of the company, as I have a commitment to a contract that runs for six months in 2025. As the company grows and if there was some traction I would hope to move to full time.

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?
    Answer: I’d focus on technical product development and strategy pre-product/market fit. Post-product/market fit, I’d want to transition into a more leadership-oriented role, steering innovation and scaling operations.

  2. How do you see your role changing as the company starts to scale?
    Answer: As the company scales, I envision delegating day-to-day responsibilities and focusing on mentoring, high-level strategy, and ensuring operational efficiency.

  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?
    Answer: I’d transition into a technical advisory or innovation-focused role, continuing to add value by steering product and technology development.

  4. Areas of Responsibility (AoR) Exercise

Area of Responsibility Self-Assessment (1-10) Passion
Sales 4 Low
Marketing 5 Medium
Product Strategy 9 High
Design 6 Medium
Engineering 10 High
Operations 8 Medium
Fundraising 3 Low
Leadership 8 High
Company Building 7 Medium
Recruiting 6 Medium
Legal 4 Low
Specific Skills 9 (AWS, Data Engineering, Automation) High

Preferred Areas of Leadership: Product strategy, engineering, and leadership tasks based on high passion ratings.

Part II: Corporate Structure and Funding

  1. Where should our startup be based? How do you feel about remote or distributed teams?
    Answer: I’m comfortable with remote or distributed teams. If a physical location is necessary, it should be decided collaboratively.

  2. Is there anything I should know that may materially affect your time or legal status as a founder?
    Answer: No issues. I’m a British citizen with no legal restrictions.

  3. How should founder equity be set? What’s your philosophy on the employee equity pool?
    Answer: I believe in an equal split among founders and adhering to Y Combinator’s guidelines for employee equity pools.

  4. What should our approach to employee compensation be, including cash and equity?
    Answer: A balance of cash and equity, tailored to attract and retain talent. Suggestions from Y Combinator and experts like Scott Galloway should guide our structure.

  5. How much money should we raise?
    Answer: I favor a frugal approach, raising only what’s necessary for sustainability and growth.

  6. What matters most in a funder?
    Answer: Integrity, alignment with our vision, and a collaborative approach to governance.

  7. What does an ideal company exit look like to you?
    Answer: While I’m open to possibilities, I lean toward long-term involvement, provided it remains fulfilling.

  8. How do you think about the timeframe and pace of success?
    Answer: I’m open to a longer path but need clear milestones to maintain motivation.

  9. What number would you sell at? How would that change if you got extra liquidity from your existing positions?
    Answer: It depends on market conditions and personal engagement. If I enjoy the company’s growth, I’d prefer to stay longer.

  10. What do we do if we find product/market fit, yet none of the founders are excited about that product?
    Answer: We should assess the reasons for disinterest and either delegate or pivot based on market feedback.

  11. Can one co-founder fire another co-founder?
    Answer: This should be governed by a legal framework and pre-agreed terms.

Part III: Personal Motivation

  1. Why do you want to start a company — in general, and in particular right now?
    Answer: I enjoy the challenge of entrepreneurship. My goal is to transition from exchanging time for money to creating products that generate value. It’s an opportunity to try something new, gain fresh experiences, and leverage my skills.

  2. What is success to you? What motivates you personally?
    Answer: Success is about creating value, working on meaningful problems, and building solutions that align with my interests. I’m motivated by curiosity and the desire to contribute to something impactful.

  3. What impact do you want to have? Is your startup objective “getting rich” or “changing the world”? Is control or success more important?
    Answer: I’m open to stepping aside if it leads to a better financial outcome for the company. My primary goal is neither wealth nor world-changing impact but pursuing something that interests me while retaining creative control.

  4. What makes you gritty?
    Answer: Is this a trick question? I had to Google this one, but According to this article (Dr. Damian Vaughn), grit is made up of the following: Perseverance, Resilience, Courage, Passion, Conscientiousness.

  5. Who do you admire most in your organization/family/friends and why?
    Answer: I admire my father for his courage and determination to reinvent his career in his 50s, transitioning from a management role to a fulfilling path in local politics. Similarly, my mother inspires me with her decision to prioritize her passion over traditional career ambitions. My brother has been a significant influence, providing guidance and inspiration for my own career journey. Lastly, my cousin, the COO of his own company he started in his 20’s.

  6. What are you most proud of in your work career or life to date?
    Answer: Earning my degree in physics is a significant achievement. It required hard work and dedication, and I’m proud of the effort I put into it.

  7. When have you taken a chance when others did not? Or when have you been willing to take an unpopular stance?
    Answer: I percieve myself as an early adopter and will try and new tools to assist me with work. Few members of my close family or friends have gone into entreprenurship so by some degree I could be seen as taking a risk in this circle, but not so much in the wider community.

  8. What are some of the products and companies you love, and why?
    Answer:

    Products:

    • Balatro: An exceptional game by a solo developer, showcasing innovation on an obscure platform.
    • iPhone: I’ve never used another brand of phone—it’s reliable and intuitive.
    • Steam Deck: A fantastic idea that bridges portable and PC gaming.
    • Nintendo Switch: Combines innovative gaming and portability, with a library of beloved franchises.
    • PlayStation Consoles: Known for their high-quality games and immersive experiences.
    • Nintendo Consoles: Consistently innovative, delivering iconic titles that span generations.
    • Sausage and Egg McMuffin: A breakfast classic I can never get enough of.
    • Induction Hobs: Recently switched to one and might never return to conventional gas cooking.
    • ChatGPT: A transformative AI tool that makes productivity and creativity more accessible.
    • Gmail: A revolutionary email service when it launched, vastly improving on traditional tools like Outlook.

    Companies:

    • Coca-Cola and McDonald’s: Exceptional brands with unparalleled global recognition and consistency.
    • Red Bull: Their innovative marketing and transition into extreme sports culture are impressive.
    • PlayStation: Consistently delivers top-notch games and immersive gaming experiences.
    • Nintendo: A 185-year-old company with a storied history and franchises like Mario and Zelda that define gaming.
    • IKEA: A genius in blending affordability, design, and customer experience.
    • Valve: A unique company structure, and they’ve evolved from game development to platforms like Steam and now hardware.
    • SpaceX: Highly innovative, with captivating launches and landings that redefine space exploration.
    • Oxford & Cambridge Universities: Iconic historical brands that are synonymous with academic excellence.

  9. Is it possible to build a wildly successful company without burning out or damaging other parts of your life (family, health, etc.)?
    Answer: I suppose anything is possible with the right mindset, strategies, and boundaries in place? Balancing success with well-being requires intentional planning and adaptability.

Part IV: Commitment & Finances

  1. Will this company be your primary activity? Do you have any other time commitments?
    Answer: I’ve been accepted to an Indie Game Development master’s program starting January 2025 and have a contract commitment for 2025. However, I can exit the contract on short notice if the startup shows significant promise.

  2. What is your expected time commitment right now? How do you see that changing in the next 6 months? 2 years?
    Answer: Currently, I can dedicate 20 hours per week. If we establish a viable product and business model, I’m prepared to transition to full-time within six months to two years.

  3. What is your personal runway? Current burn rate? Would you invest your own money (ideally retaining higher equity in return)?
    Answer: I have a personal runway of 12–18 months and am willing to invest my own funds if required, with the expectation of retaining a higher equity stake.

  4. What is the minimum monthly salary you need to survive? To be comfortable? To feel like you’ve “made it?”
    Answer:
    • Minimum: £5,000/month to cover living expenses.
    • Comfortable: £10,000/month to ensure financial stability.
    • “Made it”: £100,000/month as a measure of significant financial success.
  5. What should the policy of co-founders advising/consulting with other companies be?
    Answer: I’m uncertain about this and would need to research best practices to ensure fairness and alignment with the company’s goals.

Part V: Team Culture

  1. Complete the sentence: It would make you proud to hear people describe this company’s culture as _________________.
    Answer: Innovative. A culture where creativity, adaptability, and forward-thinking solutions thrive.

  2. What’s your philosophy on how to attract and retain great people? Tactically, how would we make this happen at our company?
    Answer: While I need to research this further, equity could be a strong motivator for attracting and retaining talent. Offering clear career growth paths and fostering an inspiring work environment would also play key roles.

  3. 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?
    Answer: I’d explore methods such as regular performance reviews, mentorship programs, and creating opportunities for professional development. Encouraging open communication and celebrating achievements would also be essential.

  4. How much of your time do you hope to spend either working or socializing with coworkers?
    Answer: I’d aim to balance my time effectively, focusing on work-related collaboration while occasionally socializing to strengthen team rapport.

  5. How important is diversity & inclusion? Concretely, how would you put that into action?
    Answer: Diversity is essential for fostering innovation and avoiding homogeneity. I’ve worked in teams lacking diversity, which became monotonous. To address this, I’d set diversity benchmarks, actively recruit from diverse backgrounds, and create policies that ensure inclusion and equity across the organization.

Part VI: Co-Founder Relationship

  1. Specifically, how are we going to prioritize and make time for our co-founder relationship as we get increasingly busy with company building?
    Answer: We would schedule regular meetings focused on both professional and personal alignment. These check-ins would help maintain open communication and address any potential issues early.

  2. How would we resolve personal conflict between ourselves? How about stalemates?
    Answer: For conflicts, we’d use established conflict resolution techniques, such as mediation or facilitated discussions. For stalemates, we could implement a system where each co-founder has domain-specific decision authority to break ties.

  3. In case this becomes part of our partnership’s evolution, how would you go about handling a startup divorce?
    Answer: While challenging, it’s essential to handle a potential separation amicably. We’d need a pre-agreed framework to manage equity, responsibilities, and transition smoothly.

  4. 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?
    Answer: Diagnosing the problem would involve a candid review of our strategy, execution, and market dynamics. Gathering data and seeking external feedback would help identify and address growth barriers.

  5. 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?
    Answer: Open communication is key. Regular feedback sessions and a willingness to adapt based on mutual understanding would help mitigate resentment.

  6. How would you think about bringing on a third (or N+1) cofounder?
    Answer: I’m open to bringing on a third or even a fourth co-founder if they fill critical skill gaps and align with our vision and values.

  7. 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?
    Answer: We would need clear goals, transparent communication, and mutual support. Setting expectations and holding each other accountable would ensure we stay aligned and foster a successful partnership.

References

  1. Lin, Gloria. The Founder Dating Playbook: Here’s the Process I Used to Find My Co-Founder. https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder/.
  2. Dr. Damian Vaughn, PhD. What Is Grit? 5 Ways to Develop It without Burning Out. https://www.betterup.com/blog/to-be-great-grit-isnt-all-that-matters.

References

  1. Lin, Gloria. The Founder Dating Playbook: Here’s the Process I Used to Find My Co-Founder. https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder/.
  2. Dr. Damian Vaughn, PhD. What Is Grit? 5 Ways to Develop It without Burning Out. https://www.betterup.com/blog/to-be-great-grit-isnt-all-that-matters.

Posts

References

  1. Lin, Gloria. The Founder Dating Playbook: Here’s the Process I Used to Find My Co-Founder. https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder/.
  2. Dr. Damian Vaughn, PhD. What Is Grit? 5 Ways to Develop It without Burning Out. https://www.betterup.com/blog/to-be-great-grit-isnt-all-that-matters.

Posts