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Tips for finding and vetting a cofounder

An approach to figure out if you're a good fit for working together

Mar 22

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The best way to figure out if you want to work with someone is to work with them. This sounds incredibly obvious but practically nobody does it. Instead, they resort to complicated artificial case studies or gimmicky interviews that’ll magically “reveal” if you’re a compatible match. Those approaches seem pretty voodoo and ineffective to me.

So what’s the alternative?

I’ll walk you through an extremely practical approach to vetting whether or not you want to work with someone. This applies to co-founder searches (and also to teammates in general but it’s more focused on the former). I’ll also cover some strategies you can use to find someone to work with.

By the way, if you are looking for a co-founder, you should check out Friends of Next Play. When you join, you get invited to our Slack, where you’ll meet other people who are thinking of starting/joining companies.
You can join Friends of Next Play here.

How to vet a co-founder or early teammate

When I say figuring out how to work with someone by working with them, I mean it extremely literally.

I think this is the stage where people go wrong. They don’t actually work with someone. Rather, they treat the process more like a long interview. They don’t actually try to make it work. They do not give any real authentic trust to the other person. And then they are surprised when it does not work out. Or when the person is acting a bit weirdly. Duh! It’s because the whole situation feels inauthentic and fake.

My advice: Get in a room together. It can be digital but physical is better. Go spend a few days days working together on something REAL. That’s an important aspect. It’s not a made up case study. It’s not some logic puzzle you invented or read on Twitter.

It’s a real problem you actually want to solve.

If you already have a business idea in mind, it’s an actual problem from that business. It’s finding customers. Or building a part of the product. Or building out a financial model.

If you don’t yet have an idea, then it’s a practical thing that’ll help you get there faster: “Together, we are going to build this site to interview these customers to see if there are any interesting projects to build.” Or maybe it’s an actual essay you want to write together. Or even a trip you want to plan.

Whatever you do together, just make it as real as possible. Together, you focus on doing the short term thing. The real thing. While you are working, of course you may talk about longer term ideas and philosophies and values. Those things naturally come out. You’ll figure out if things are weird. If you like sitting next to each other. If you like getting lunch together. If you are generative or destructive with one another. You’ll learn a lot.

This is what I would describe as a good version of a work-trial. Because it’s a literal trial of working together.

I see bad versions all the time. Where someone comes in for a work-trial but it’s really like a weird type of interview that’s destined for failure. You want to avoid weird power dynamics that stifle productivity. That distort your findings.

This whole thing is not necessarily a long-term commitment. You are seeing how well you work together. If, at the end of the period (be it a few days or a month), things are not obviously great, then you should probably end the engagement.

Obviously great means both sides are very happy. To figure that out, you should be sure to give each other space. You don’t want to pressure or love-bomb (metaphorically) the other person into working with you. People can be easily influenced and caught up by momentum. Beware of this - you likely want to figure out if they are genuinely interested in working together over the longer term.

If you are worried about IP or confidentiality, that can be a bit tricky. One option is not to worry about it but that can also backfire. I’d say slicing off a piece of the project is a good way to manage this but you do run a risk. If you’re worried about someone stealing something you see as important, then try to run more background checks on someone before working with them.

Now maybe you’re like sure this makes sense once you are down to a few people who you could potentially work with, but how do you vet people further upstream?

Vetting people you have not actually worked yourself with is hard. Hard because you’re then relying on other signals to communicate potentially complicated nuanced situations.

Every tactic has its faults but here are some that I’d recommend at least exploring, in order of what I think is most likely-to-be-useful:

References: Talk to people the person has actually worked with before. The hard part about this is needing to vet the person you’re referencing. Are they good? Do they have a good bar? I would just take everything they say with a grain of salt. Instead, I’d look for the extremities in their language: this person is outstanding at X. This person is really bad for Y reason. I would not make a decision based on one reference but it can be useful information to help you make a decision. I would be nervous about working with someone who refused to provide a reference or was not able to provide many references. I like this essay by Graham Duncan on this topic.
Outputs: What has the person actually built or done themselves? Beware of people taking credit for things they were not personally responsible for. Ask them the details - the people who actually built the things can remember the details. People who were just in the room or on the project but not really contributing are going to be a lot fuzzier. You may be able to find this online but what you are looking for is proof of work.
Revealing questions: Some people have a hard time talking about themselves. Instead, ask questions about what people admire? Who do they look up to? Asking these types of questions is a good way to figure out what they find important. More thoughts on this here.
Compatibility: I cannot emphasize this enough. If you are going to be working with this person for years or potentially decades to come, figure out if you like each other. You don’t have to be best friends but you will probably spend a lot of time together. Figure out if that’s a good or a bad thing. Will that get in the way at all? One different thing I’ve seen people do that’s sometimes useful is to hangout as a group with each others’ families or significant others. You don’t have to do this but it could be a way to see what each other are like.
Understand their overall journey: I am skeptical of working with someone just because they have a bunch of fancy logos. Ask them why they chose each job. How did they get each job. I like to figure out where people have struggled. Struggle isn’t bad. And sometimes people hide it because they see it as a weakness. I think it’s more of a strength. How do people handle rejection and failure?

Hopefully the above are useful steps you can take to vet a co-founder. If you need more thoughts around finding a co-founder, you can check this out: