I have recently incorporated a company here in the Philippines, and while I’m still a solo founder, I acknowledge the fact that I need a team to start and grow the business with me. Many years ago when I was looking for a co-founder for a startup project I’m building, I compiled this list of questions that my potential co-founder and I answered together, and it really helped us decide on the setup of the engagement.
Building a company from scratch is like setting sail on a vast and unpredictable ocean. In this exhilarating but often tumultuous expedition, choosing the right co-founder is like selecting a trustworthy navigator—someone who shares your vision, complements your skills, and steers the ship with unwavering commitment. It’s true what they say, it’s exactly like finding a wife.
To ensure a harmonious voyage, here’s a comprehensive list of questions you and your potential co-founder should explore together.
Full List of Questions You Should Ask Your Co-Founder
Motivation, Mission & Vision Alignment, Sense of Commitment
- Why do you want to build a startup (in general and in particular, right now)?
- What is your long-term vision for the company?
- How do you see our mission making a real impact?
- Are your personal values aligned with the values we envision for the company?
- What are our respective personal goals for the startup (e.g. a sustainable business that is spinning off cash and running it forever or high growth and some type of liquidity event)?
- What is the most attractive thing about this venture opportunity?
- How would you define its ultimate success for YOU? (revenue, exit, personal pride, etc)
- What is your biggest concern?
- How would you define its ultimate failure for YOU? (financial loss, broken relationships, etc.)
- How do you see this opportunity working in your overall career and personal path?
- If this venture fails and we don’t achieve the vision and outcome we worked so hard for, what would be important for you to retain personally? (Pay severance, reputation, relationships, etc.)
- What is the expected time commitment (now, in 6 months, 2 years, etc.)?
- What are your personal and professional goals for the next five to ten years?
- How do you envision your role in the company evolving over time? Get a sense of personal commitments that the person has so as to better manage your time and their time (i.e. are you married? With/without kids?)
- If you’re not able to go full-time now, under what circumstances would you be able to start working on something full-time?
- Will this be the primary activity for each of us?
- What are some of the core beliefs/principles we’re agreeing on regarding the venture itself?
- What do you think is the biggest opportunity here?
- If we got rid of XYZ, this company would NOT work. What is XYZ?
- Things may totally evolve as we both know. Business models may shift, customer targets may change, and our whole business focus could be different. Are there certain types of models or aspects of the venture that you fundamentally would not do? Why?
- What do you think our biggest risk is with this venture?
- If we had to make a total pivot into a completely different industry, model, product, etc. to survive, what would be your reaction? (Pick a crazy different industry to test this out.)
Company Structure and Legalities
- Who do we think the first 5 hires will be?
- Where do we want the business to be located?
- Will any of us be investing cash in the company? If so, how is this treated? (e.g. debt? convertible debt? Does it buy a different class of shares?)
- How do you feel about investing your personal finances into the business?
- What are our personal cash needs in the short term?
- Are we both going unpaid and when would this change?
- What level of financial commitment are you comfortable with?
- Do we want to raise outside money?
- If so, how much – now, in 6 months, 2 years, over the life of the company?
- Who is going to be CEO (and why)? Are we both comfortable with this?
- What’s the equity split and why? Are we both comfortable with the reasoning behind this decision?
- How do or how did we decide what roles/titles we would hold? Are there any concerns with how we are executing on that?
- Is one person more of the front-facing person to the public or to investors? In situations where you had to have just one “face” of the company, who would that be?
- How are we splitting equity? Is this formalized through a legal document? (It should be!)
- What if one of us put our own funds into the company and that gave that person more equity overall, is that okay? Or do we want to intentionally maintain the equity split we agree on. How will that play out in the future with our different roles? What are potential issues that could arise when those opportunities happen?
- What if one of us leaves? What will happen to their equity? Is there a vesting period?
- Are we allowed to take on anything outside of the company?
- How will we determine compensation for each other as founders? Is it similar to the equity split or our role?
- What if we only had enough funds to pay one person. How would we decide that?
- What if we didn’t have enough funds to pay salary for everyone for a while, how long would you or your family be able to survive? Would you need to get another job?
- What is your vision for the company’s exit strategy?
- How do you feel about potential acquisition offers?
- Would we sell this for $5mm? $100mm? Are we waiting for the billion dollar exit?
- How much equity are we allocating for future employees?
- How will decisions get made?
- Can you outvote me?
- Can either of us fire the other?
- If one of us gets fired, what do we leave with?
- Have you ever been fired, gone to jail, or done anything that would materially impact your time with the company?
- Do you sit on any boards of companies and do you have any conflict of interest with our project?
- Is there a ‘no compete’ clause that is active at this time?
- What if an investor wanted to invest (or a vendor/partner would only work with us), but expressed that you weren’t the right person? How would we handle that assuming that the company really needed the money?
- What are some 3 or 4 deal breakers in terms of working together? (Ex: super negative and attacking language, going behind the other person’s back, etc.)
- What if we fundamentally disagreed on a key decision. How would we resolve it? Let’s think ahead about the process we would follow.
- Is there someone we want to put in place to be our trusted person who could help us process this disagreement?
- What if one of us caught the other doing something unethical? How would we handle it? Are there any examples from that past where this happened?
- What do you consider ‘unethical’?
- How have you been burned by another partner before? Based on that, what are some sensitive aspects that you want to be super intentional about?
- What areas/decisions would you like to have the final say?
- How are we going to handle decision-making with 3 partners? Do we each get our own area? Who makes the final call?
Your Partnership with Each Other
- What are your strengths and weaknesses as a leader and co-founder?
- What specific skills do you bring to the table?
- How do your strengths complement my weaknesses, and vice versa?
- Are there skills we both need to develop for the benefit of the company?
- What is missing between us in terms of skill set or expertise that you think we need to succeed?
- What areas do you see yourself definitely wanting to be point-person on for the first 12-18 months?
- What are the areas you know you’re not particularly good at?
- What do you think I am best at?
- What do you think I need support for?
- How will you help me succeed?
- Why do you think we’ll be good together?
- What makes you most excited to work with me?
- What is the ‘super power’ quality that you most value in me? Is that aligned with my own self-assessment?
- What concerns do you have about working with me? Are there weaknesses I should be aware of?
- What is the ‘pet peeve’ you have (or potentially could have) with me?
- Do the superpowers in the other person make me feel insecure? If so, why and how can we proactively manage this?
- What’s the one thing I would NOT want to change in the way we’ve worked together?
- What’s the one thing you DO want to change in the way we’ve worked together?
- What faith or core principles do you live by? What does that look like on a day-to-day basis right now?
- Share your faith journey with each other.
- Where have you struggled the most in your faith?
- What are some of the key pivotal moments that may be relevant to this venture, our partnership, and/or what you’re currently learning?
- Can we commit to keeping each other accountable? How frequent do we want to set aside time for this?
- What practices do we want to commit to doing together for our partnership and venture?
- How can we best support each other in our faith journey as we hustle in this venture? (Required rest, keeping each other accountable, etc.)
- What types of conversations do we keep private between us? (Personal financial situation, personal struggles, etc.)
- How do we make sure that we honor that privacy? Do we ask each other permission before sharing anything that are in specific buckets?
- How do we talk about the other person in public? (even if we disagree with each other)
- How do we want to present ourselves in public?
- Who does most of the talking? Are there areas that we each will own? How do we prevent talking over each other?
- What would be our key communication rules for our partnership? (ex: never speak for the other person, never criticize/correct the other while in a pitch meeting, always be transparent with key conversations when the other person was not present, etc.)
- Can we commit to an ongoing check-in to openly and honestly discuss our partnership on a weekly/monthly basis? The purpose is to discuss things before they become big problems.
Personal Work Style, Habits, Ethics, Preferences
- What motivates you (e.g. a technical challenge, an overall problem, helping the world, etc.)
- What is your work style—do you thrive in structured or flexible environments?
- How do you handle stress and tight deadlines?
- Are there any ethical considerations that matter deeply to you?
- If you had to come up with 3 words to describe the culture you want to create, what would they be (e.g. open, hard-working, eccentric)? Pro-tip: if you’re really serious and far along go visit few office spaces together to get a sense of what each of you likes work environments wise and why.
- What are some of the products you love and why? Pro tip: this will help you get a sense for they appreciate and even aspire to – design, product, tech, biz strategy, etc.
- What values do we want to instill in our employees?
- If you could pick 2 things to change and two things to bring with you from your previous companies, what would they be and why?
- Have you worked and/or managed diverse teams and if so, how?
- How do you think we should give feedback to each other (and the team)?
- What do people say is your “super power” or consistent contribution on the team?
- What is something you’re currently working on in terms of improvement?
- How would you characterize your work style?
- How do you best process? (externally through discussions, quiet time alone, etc.)
- Is your work flow generally uninterrupted or are you okay with starting and stopping things at moment’s notice?
- What work environment do you work best in?
- Describe yourself as a leader. Describe yourself as a manager of people.
- How do OTHERS describe you as a manager/leader?
- How do you deal with conflict? Compromise?
- How comfortable are you with taking calculated risks?
- Can you share an experience where you took a significant entrepreneurial risk?
- How do you handle conflicts or disagreements?
- Are you open to constructive criticism, and how do you deliver feedback?
- Have you experienced a significant disagreement with a previous business partner, and how was it resolved?
- How do you feel in high pressured and stressful situations? How do you like to process and handle those moments? Do you need time before you respond or do you like to dig in together?
- How do you see yourself balancing work and personal life?
- What would be your reaction or approach if you felt burnt out? Has that happened to you before?
- What are some of your life rules: the ones that structure your work/life + the ones that define your limits?
- How do you envision the day to day work at this startup?
- How does your family feel about you doing a startup?
- What would happen if your family turns against this? Has that ever happened where your loved ones are discouraging to what you do? How did you react?
- What are some key pressures in your life that would put pressure on the startup?
- What is your one thing that you ‘know’ has been the major issue in past partnerships?
- Describe your best/worst partner.
- How are you most encouraged by someone both in professional and personal settings? Is it the same or different?
- What is your ‘love language’ in the work space? In other words, what is your form of appreciation? Words of encouragement, public recognition, acts of service, gifts, etc.
- How do you handle conflict or something you deeply disagree with?
- How do you ‘fight’ or argue?
- What makes you most proud?
- What makes you feel most ashamed?
- What would cause you to quit without question? Do you have some strong beliefs or philosophies that mean a lot to you?
- What would cause you to fire someone without question?
- Do you feel responsible for the well-being of each other’s family? What should we worry about and what do we need to let go of? Is there a part of our plan that we are unwilling to change (e.g. the product being built, the market being addressed or some other aspect of the company)?
- How do you prefer to communicate—via email, phone calls, or in-person meetings?
- What tools or platforms do you find most effective for collaboration?
- Have you ever failed at anything?
- Have you been involved in a startup or entrepreneurial venture before?
- What were the successes and failures of your previous entrepreneurial experiences?
- Have you ever failed at anything?
- If so, how did you handle it and what did you learn? If not >> big red flag!
- How comfortable are you with pivoting the business model if necessary?
- Can you share an experience where adaptability played a crucial role in a past venture?
- What do you do with your free time? (e.g. how do you unwind? How do you deal with stress and big challenges?
- What do you think I’d be most surprised to find out about you?
- Are there personal or professional boundaries you want to establish from the outset?
- How do you manage work-life balance, and what expectations do you have regarding this?