A Guide for Early Stage Founders
13 Questions (and Answers) to Find Exceptional Co-founders
Co-founder dating is tough. Here are the questions you should use to assess and probe mutual fit.
As a startup founder, having the right co-founder can have an astronomical impact on whether your startup succeeds or fails.
Since the founding team is the biggest determinant of your startup’s success — it makes sense to conduct significant due diligence before committing to a years-long partnership.
So how did I determine who I wanted to work with? The first step I took in my 30+ co-founder interviews was to fill out an asynchronous questionnaire to assess mutual fit and probe compatibility.
Here are the exact questions I used, along with my own personal answers to serve as a reference:
Note: You can create your own questions by referencing First Round’s 50 Questions to Explore with a Co-founder, taking pertinent snippets from different sources on the internet, or mixing and matching all of the above (which is what I did).
How you operate
1. What are your biggest strengths and weaknesses? How do you try to compensate for them?
Biggest strengths:
- Repeat founder. I have battle scars, mistakes, and tribal knowledge I can channel to move 2x faster vs. my first time around
- Esoteric industry experience across multiple vectors: Over the past 7 years of founding startups, I built up an amazing network of investors, founders, advisors, and customers, who can collectively help me solve any problem. I built and scaled zero-to-one products across B2B Marketplaces, B2B SaaS, and Product-Led Growth — picking up a diverse set of skills I can apply anywhere
- Dangerous enough generalist: I’m competent enough to deliver value across sales, product, engineering, and design to move the needle forward with limited resources. I’ve built and led teams of 10+
Biggest weaknesses:
- Sometimes I’m blinded by the excitement to build and have the tendency to take action without a deeper level of due diligence. I’m cognizant of this flaw and it’s something I’m looking to improve (i.e. setting aside for strategic thinking time)
- Could be better at fostering culture. I don’t tend to celebrate wins or smell the roses as much as I should. I can be tough on my team (and myself) to deliver results — forgetting that results often take time. Trying to get better though!
2. How would your co-workers describe what it’s like to work with you?
- Fast-paced and results-oriented. But also funny, relaxed, and easy to talk to/relate to.
- Leads by example and is always looking to give and receive feedback.
3. How do you cope with stress? Depression? Are there any red flags I can help watch out for?
- In the past: not well. I did a poor job of dealing with stress — where I led an unbalanced lifestyle and treated work problems as existential ones. Now, making a better effort to fully disconnect from time to time, celebrate wins, and enjoy the journey of growth and learning.
- Red flags: micromanaging — trust needs to be the basis of a successful co-founder relationship.
4. In an ideal world, how many hours/week are you willing to work? What sounds good? What sounds like hell?
- I’m willing to work a lot (i.e. 70-hour weeks), but belive output trumps input — we shouldn’t be competing to see who worked more or less. We should be intrinsically motivated to maximize value for our company (while staying sane).
- What sounds bad: fully remote, async, task-oriented work.
- What sounds good: in-person or structured hybrid setting, core working hours, days set aside for deep, focused work and days set aside for strategic discussions
Roles, Structure, Funding
5. What would you want your role to be before we reach product/market fit?
- Pre-PMF: This should be determined by who’s the best person for the role, depending on problem space, experience, and desire.
- Personally, I enjoy roles where I have the latitude to wear multiple hats and spearhead strategic initiatives across the organization.
6. How much money should we raise? (i.e. “zero” or “as much as we can”)… when do you think is the right time or cadence to bring in outside investment?
- As much as we need. The market is tough right now, and I’d rather not introduce unnecessary dilution unless it’s strategically valuable. Funding is a means to an end — revenue and profitability is the ultimate validator to whether you’re building a great business.
- But we should keep in mind that raising can open up strategic corp dev opportunities, increase the hiring pool, and positively impact our own motivations.
7. What does an ideal company exit look like to you?
<Redacted>
Motivations
8. Why do you want to start a company — and why right now?
- Entrepreneurship is the most profound opportunity to learn, grow, and maximize impact. You get to build something from nothing, work alongside some amazing gritty people, and have a real impact on real customers.
- Why now: I think there are a lot of opportunity spaces that are untapped and I have high conviction that I could be the one to solve them.
9. What is your personal runway? What is the minimum salary you need to survive or be comfortable?
<Redacted>
10. 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?
- Goodwill doc: create an agreement at the start to stipulate what happens when dissatisfactions aren’t addressed over time.
- Bi-weekly check-in: provide tangible feedback and give kudos on what you think the other party can do better.
- Radical candor: sharing honest feedback early and often. Resentment needs to be nipped at the start — once it festers and builds, it’s really hard to reverse it.
11. How would you think about bringing on a third (or N+1) cofounder? If yes, when would be the right time?
- If the person can bring massive value — 100%. A good indicator for this question is: “Could this person build a billion-dollar company with or without me?” If yes, I would try to get them on board, fast.
- Plus, I’d rather have a small piece of a massive pie rather than a big piece of a small pie.
12. What type of progress would you need to see to fully commit? Do you have a target timeline for when you need to observe this?
Depends on the problem space but generally:
- Strong conviction in the team (good personality fit, skillset match, interest alignment, founder-market fit)
- Conviction from co-founders on problem space;
- Economics: TAM, pain points/willingness to pay, theoretical CAC/ACV;
- Convergence on a singular set of problems via customer discovery;
- Early signs of PMF (design partners, paying customers, usage rates, novel technological breakthrough, organic referrals);
- Progress on MVP + go-to-market;
13. Reference Checks: are there two people you’ve worked with that can speak on your potential as a founder?
<Redacted>
During this reference call, ask questions aimed at reaffirming the answers listed in your co-founder’s questionnaire.
For instance, I would ask references questions like:
1. Would you (re)hire or co-found a company with this person? Why or why not?
2. If you had to rate their competency in {critical skill} out of 10, what would it be? Why?
3. How would you describe what it’s like to work with {name}?
4. What is the most impressive thing {name} has built?
If you found this article to be helpful, connect with me through my personal blog or Linkedin to receive helpful tips pertaining to the early-stage founder journey.
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