Ten questions I would ask a potential cofounder – part 2 of 2
A helpful guide for anyone who is in the process of finding a good fit for their next venture
In case you missed it, part 1 of 2 is available here.
As mentioned, I’ve spent a long time compiling this list of questions. Too many people fast forward through the cofounder dating process. They jump straight into building a company, only to discover cracks in the foundation months later. Finding the right cofounder is the one stage of starting a company where measuring twice to cut once always pays dividends.
In part one, the questions focused on the company and investors. This week, the second set of questions focus more on a potential cofounder and what they bring to the table.
Once again, there really aren’t any wrong answers. Particularly for these questions, each answer needs to be considered in relation to your own answer. How well do your perspectives mesh with each potential cofounder’s? Are they the right counterbalance for what you bring to the table?
6: What do you envision to be the scope of your role? How do you anticipate this changing as the company grows?
“Cofounder” can mean many different things, as can “CEO,” “CTO,” “COO,” etc. Does this entail being an individual contributor (IC) or being a team lead? Does this involve being part of the executive team? As the company gets larger, do you think you’d take on a smaller role and hire other leaders to run some or all of the functional groups under your purview?
7: What sorts of decisions do you want to own? Where do you want to have partial involvement or no involvement at all?
This will deepen the conversation around scope and role. Do the sorts of decisions that each of you want to own overlap or complement one another? Are you both interested in being involved on the decisions where dual input matters? Are there any decisions where one of you is looking for independence but the other wants to be involved? Eventually, as you grow your team and the business expands to have other leaders, this will be an important discussion to come back to. However, being well aligned going into the early days of a startup is critical for ensuring you can move quickly and efficiently and avoid conflict.
8: What are your unique strengths as a leader and as an individual contributor?
This is a chance not only to pressure test how self-aware your potential cofounder is but also to better understand if their strengths match the role that they want to hold. If they talk about wanting to be an IC but don’t have the strongest analytical or technical skills, then this could be a cause for concern. If they talk about wanting to be a people leader but don’t have an interest in thinking about things such as compensation structure and career ladders, that could also be a flag.
9: What are your unique weaknesses? What’s your plan for addressing these?
This is an opportunity to understand a potential cofounder’s growth mindset. In addition, it’s a moment to step back and look at both of your skillsets together. Ideally, your weaknesses are going to be complementary, such that you can support each other to deliver better outcomes together. It’s unrealistic to expect a plan to address every single weakness – instead, focus on understanding if the weaknesses that each of you bring to the table would create any particular challenges for the roles you’d respectively like to hold.
10: What are you willing to sacrifice personally for this company? What are you not willing to sacrifice?
You never know how things will go with a startup. Talk through scenarios such as if funding runs out and it’s a tough market to fundraise. Are you willing to take no salary? A lower salary? Or in a less dire situation, for example: If the budget for team bonding has run out, are you willing to pitch in your own dollars to do a morale event? If the office needs to be cleaned, are you willing to spend your own time and energy on cleaning it up? In a best case scenario, if the company is a huge success, what personal sacrifices are you willing to make in order to put the company first?
Cofounding a company together is deeply personal and you need to understand just how personal each of you is willing to get. In an ideal scenario, you both have similar answers and willingness – whether it’s a little or a lot doesn’t matter. This is a domain where alignment and similarity of response makes the biggest difference.
Is there anything else you’d add to this list? Drop it into the comments ⬇️