What Interview Questions should I ask a Startup Cofounder?

Howdy, Upstarts!

This question is incredibly important for building startups because it is so easy to find people to work with who appear excited about your startup at the moment, but who can’t seem to stay focused on delivering your product.

Uncommitted startup cofounders will slow you down and will destroy your Cap Table, so finding people who fit just right, those Goldilocks Teammates, is an important challenge for every startup to overcome.

Talent wins games, but teamwork and intelligence win championships.

As the ancient proverb says:

“If you want to go fast, then go alone; but, if you want to go far, then go together”.

When I was a young student in university, cock-sure, sarcastic, and impatient, I hated group project assignments.

You know the ones!

Our teachers always insisted on teaching the value of teamwork and so they would assign our classes group projects, forcing into small squads of students. Inevitably, most of my teammates spent their nights chugging Pabst blue ribbon or slaying the Covenant, while the handful of us concerned with making the Dean's List would slave away until the early morning to carry the weight of our indolent associates. Those projects always had an unequal distribution of labor, which is the case whenever a project is more important to some than it is to others.

I hated it!

But, I'm not bitter...

And to add insult to injury, every professor would use this old sophism: without a team, you will never be able to accomplish my goals in life. In the real world, you work in teams!

To reach my long term goals, I need to tolerate and moderate the speed of these, shall we say, less-capable team members. I hated this answer, but I respected my mentors enough to give them the benefit of the doubt and to consider their wisdom.

And I can honestly say that this is great advice when I worked at large, sluggish corporations, companies whose coffers could afford slower development timelines; however, my fellow startup founders, when you are assembling your startup's founding team, you cannot afford this dichotomy.

If you want to build a startup, then you are going to need to cover a lot of ground in a short amount of time, and so you need to find Co-founders who are both willing and able to help you do that.

Let’s Pick Teams!

This is a great question because it cuts to the heart of this matter.

Finding co-founders who are good fits for your startup is critically important to the success of your startup because your Founding Team will become your core asset for the early stages of your startup and the Founding Team evolves into the engine at the heart of your startup. Thus, both the short and long term success of your startup is determined by the Founding Team that you assemble.

The Co-Founders that you need will be Co-Founders who can help you move as fast and as far as possible.

The best startup cofounders are ones with whom you have an existing relationship. These are people that you already know. You know how they handle responsibility. You know how they operate under pressure. You know they prefer whiskey over gin.

But, these existing relationships are rare among startup founding teams. So without an existing relationship with your cofounders, you will need to rely on good, old-fashioned Candidate Interviews, which usually provide you with a much shorter observation time.

How do you detect a good cofounder?

One of my earliest jobs was designing and building radars. Radars are like bats, but with radio waves. Instead of detecting moths by bouncing sound waves off of them, radars detect airplanes by bouncing radio waves off of them.

Although there is a lot of imaginary mathematics and arcane modeling that goes into building radars, building a radar boils down to two core principles: first, the chance of seeing an airplane is proportional to the number of radio waves that a radar bounces off of it, so shooting more radio waves means better chances of spotting the airplane; second, the amount of radio waves that a radar can use to blast airplanes is proportional to the power you supply the radar with, so more power means more radio waves.

Logically, this means that you have two general strategies when you build your radar: first, you can either have a radar with a heck of a lot of power that can blast those airplanes with a heck of a lot of radio waves over a short time; second, you can have a less powerful radar that shoots the airplane with fewer radio waves over a longer time. As I said, this is a sinful over-simplification of the subject, but the root principle is incredibly valuable.

So how do radars apply to startup interviews?

Well, we can say that to understand any person you have two options: first, by getting to know someone slowly over months or years; or second, by getting to know someone quickly by bombarding them with interview questions that are calculated to reveal their personality traits. So an interview is just like a radar. You can use fewer interview questions (like weak radars that blast fewer radio waves) over a long time, or you can use a lot of interview questions and tests (like powerful radars that blast a bunch of radio waves) over a short time.

You should treat a startup Interview like a radar, bombarding airplanes with radio waves. But instead of radio waves, you should use interview questions. (I suppose that you could light up your interview candidates with radio waves, but it might impact their health insurance premiums.)

What questions can you ask, in a short time, that will identify the candidates that will help your startup to go as far as possible and as fast as possible?

To determine if a potential cofounder is well-suited for my startup, I use a loosely structured interview process that consists of three phases. Each phase of the startup interview process has the goal of answering a specific question.

Each phase of the interview should be an organic conversation, with enough back and forth to keep it interesting, much like a date. I allow my potential cofounder enough space to answer questions, recite anecdotes, provide examples, or to workshop thoughts and ideas; and, I don’t prevent our conversations from rambling or losing focus. After all, the point of the conversation is to be a conversation and not to be a meeting.

The first phase of my startup interview process is focused on identifying and understanding whether or not my potential cofounder can add Significant Value to our startup. So during the first phase of the interview, I am trying to answer the question:

Does my Potential Co-Founder have the experience, expertise, and connections to do this job?

This first part of the interview is the closest to a job interview because it boils down to listing their technical skills, career achievements, and personal history. With enough structure, this first part can be accomplished before an in-person conversation, by reviewing a resume or answering a survey. So this is the part of the interview that is the simplest and can most easily be automated. Just make sure that the person on the paper matches the technical requirements of the cofounder position: a Chief Technical Officer should be able to find bugs in your Web App, or a Chief Marketing Officer should be able to set up a Google Ads Campaign.

When I have satisfied myself that my potential startup cofounder can bring value to our startup and to greatly increase the probability that our startup will succeed, I move on to the second phase.

The second phase of my startup interview process is focused on identifying and understanding my potential startup cofounder´s Core Values. So during the second phase of the interview, I am trying to answer the question:

Would my Potential Co-Founder and I be close friends if we had met outside of this venture?

This phase is closer to a first-date then the other phases. It focuses the least on hard, technical skills, but rather it focuses on soft skills such as adaptability and emotional intelligence. I tend to ask questions about a potential startup cofounder´s communication styles, role-models, or past social challenges. Throughout this whole conversation, my goal is to understand what my potential cofounder values and how he embodies those values.

Are they honest? Are they a direct communicator? Do they challenge opinions openly, or do they prefer a more commiserate communication style? Do they lead a conversation, or do they follow? Do we share similar interests? Does the conversation flow organically or does it feel like a business meeting?

Each of these questions gives me a sense of the kind of person that the candidate is.

When I have satisfied myself that I could be friends with my potential cofounder, I move on to the last phase.

The last phase of my startup interview process is focused on identifying and understanding my potential startup cofounder´s passion and ambition when it comes to working on this particular startup. So during the third phase of the interview, I am trying to answer the question:

Would my Cofounder be willing to devote his talent and energy to executing our Venture?

This phase is focused entirely on articulating the level of commitment of the potential startup cofounder. When you and your cofounders work together, the weight and the responsibility of the startup must be distributed evenly. Although each of you should have a distinct set of responsibilities, each of you should have the same magnitude of those responsibilities; and, that each of you can step-up to the same extent to handle those responsibilities.

Although I have not found a hard-and-fast litmus test for this phase, the goal of this interview should focus on understanding the current responsibilities, goals, and energy of my potential startup cofounder.

What is the current availability of my potential startup cofounder? How much excitement does my potential startup cofounder show when we talk about our startup?

When I have satisfied myself that my potential startup cofounder shares my passion and commitment to our startup, then I am confident that this person would make a good cofounder.

That only leaves the negotiation!

Once that decision has been made then our conversation becomes a matter of negotiation. (Negotiating with a cofounder is, of course, an entirely different challenge.)

This general structure has worked well for me and for the teams that I have mentored, and I think it can provide a good insight on what key topics should be touched upon during your conversations with you potential cofounders, as well as to provide you guidance on how to structure your approach to these conversations.