5 Questions You Should Ask Your Potential Cofounder

Originally published on Forbes and Entrepreneurial Orgasms. 

You have to trust your co-founder from day one. Without that trust, it’s as much a mistake as signing a marriage license with a significant other you don’t trust (really, marriage is really just another business deal, except the final signature involves nudity). A vague feeling of goodwill is a nice starting point, but details help. Here are the questions I find best as a way to determine trust. And it goes both ways — you should be able to answer these as well. There’s no absolute, single right answer for any of these. There are however, some pretty big warning signs to look for, so I’ve added the worst case scenario answers.

Five questions you should ask your potential cofounder:

1.What are the 3 (yes, 3) biggest failures and mistakes you’ve made in your life?

Everyone makes mistakes and how they describe them is what you are looking for. Asking for three epic fails is key. The first one will come easily, second one may require some thought, usually it’s the third one where you’ll see how much honesty, transparency and soul searching they are offering. You want to know that when, inevitably, your partner makes an error that they are capable of taking responsibility, learn from the experience, and are willing to repair the problem as much as possible. Knowing what they try to avoid repeating gives a sense of where they see their weaknesses and, paradoxically, where they are least likely to make a mistake because that’s what they are most vigilant about. By seeing what your potential co-founder will respond should help you judge the key moments that have shaped them into who they are today. 

The wrong answer: "I don’t make mistakes, I’m just unlucky."

This is wrong because you want to know that they have the capacity to learn from their mistakes. Or their explanation providing that the root cause was someone else’s fault is another common deflection. It’s important to remember that everyone in life makes mistakes; we’re human. Those mistakes will be in our professional careers and in our personal lives. So right off the bat if the person responds they have not had big learning experiences then it is a huge red flag that should warn you against letting them be a babysitter let alone found a business with them.

2. What have you created that lived after you? Is being acknowledged for building something important to you?

A business is about building something, ideally something that lasts. An (honest) answer to this question can give you an idea of abstract, lifetime goals that can help improve your partnership. Or, if they haven’t thought about it, this can be a great chance to work together on what you want your shared legacy to be.

Additionally, it is important to understand in your potential partner if they are interested/ have been interested in the past in creating a product or service that is bigger than the sum of its parts. That, if necessary, they are able to outsource themselves in order to let their creation grow. This is important because it takes humility to do this and an appreciation for a larger vision.

The wrong answer: "I created everything in my last startup and all the successes are because of me."

Pay attention: Do they use the words I or we, do they take all the credit or do they give credit to the team. The second part of the question is to understand the reason why they stepped away and their mindset about being credited for their part in the creation. Fame and ego are easy to fall into when you build a successful company and it’s important to know where your potential partner stands on this, especially if they say that they influenced the creation, or if they say that they built the creation themselves.

3. What role do you feel best suited for in a company? What do you think the accompanying title should be?

I’ve written before about the perfect system for figuring out roles and titles, but broadly speaking, you want an answer that encompasses the roles you are less to do on your own or that you are less skilled at, so that all the bases are covered. At the same time, some flexibility and overlap so that you can help each other out as necessary is a good idea.

The wrong answer: "I’ll be the CEO and I can do everything." 

By understanding what title your potential co-founder would want to take, you’ll have insight into how they view themselves and feel about who they are in the company if you move forward together. By saying that you can do everything, you’re setting yourself up to be partnering with an extreme micro-manager who will not see value in you. This is a relationship destined for failure.

4. What is your financial status?

The importance of this question is to understand the financial situation of your potential co-founder and how quickly you may need to raise capital or be able to bootstrap. Are you both not taking salaries, is someone getting paid but not the other, and how are each of you going to be compensated as partners. As an example, if one partner takes $3,000 a month while the other partner does not, is this a loan from the company to be paid back at a later date, if they can’t pay it back by time X, do they need to sell their equity to compensate?

The wrong answer: "I haven't saved any money, I spent it all on these flashy clothes that I’m wearing to impress you." 

This is obviously a very worrying situation because you’re going to be pooling resources to some degree and that means you need a more complete idea of what you can each contribute comfortably, with commensurate discussions of salaries and so on. Every dollar that doesn’t go towards the business has meaning and needs to be accounted for, one way or another.

5. What do you do for fun?

No sane duo spends every waking moment working. It may sound like the best way to get a business off the ground, but it’s just a recipe for burnout. So, when you and your co-founder take a break, what goes on? Do you have similar interests? Are you both married or in a relationship or single? Do they just fill every waking moment with work and need to figure out how to balance their time? You don’t have to be best friends with your business partner, but getting to know them better in general is absolutely essential, and what they do when you’re not actively working on the business is a great way to figure out how your personalities match, or not.

The wrong answer: "My nickname is The Party Animal."

You want your potential partner to be interested in the success of your company and have the ability to compartmentalize and prioritize work over partying.