The book Founder Fallout is a hundred questions long. The reason it is a hundred is that the answers you get from the first thirty questions are almost never the true ones. You start seeing the real person somewhere around question forty. By question seventy, both of you have said something you didn't know you thought.
If you don't have time for a hundred questions, and most first-time entrepreneurs don't think they do, here are the ten I would use. Sit across from your potential co-founder and answer each one out loud. You go first, they go second. If either of you shortens an answer or laughs it off, ask it again, in different words, until you get a real answer.
Question one. What is the largest check you have ever lost, and what did you tell your spouse about it
You are looking for two things. The number, and the marriage. If they have never lost real money, that is not disqualifying, but you are the one who is going to teach them what that feels like, and they are going to blame you for the tuition when it comes. If they have lost real money and their answer about telling their spouse is unclear or defensive, that is your first big data point. You are about to be in a foxhole with somebody who does not know how to tell the truth at home.
Question two. What percentage of your total income depends on this business going well
Fifty percent is a serious partner. A hundred percent is a partner who is going to make short-term decisions because they have to feed their family this month. If the percentage is a hundred, that is fine, but you need to know it going in, and the business needs to be able to pay them enough to keep the decisions honest. Don't sign with somebody who cannot afford to lose the fight, and then get surprised when they never fight for the right answer.
Question three. What time do you actually start work, and how late do you go
Not the aspirational answer. The actual answer. If your partner starts at ten and you start at five, you have already lost five hours of overlap every day, and neither of you is going to change. That's a scheduling difference, not a moral one, and it determines whether you get to do work together or only ever hand things off. Both are legitimate, but you need to know which one you signed up for.
Question four. How do you behave in a crisis you did not cause
You are looking for a specific story. Not a philosophy. A time somebody else broke something they were supposed to be responsible for, and your partner had to clean it up. If they cannot think of a story, they have never been responsible for enough. If they tell you a story and the villain of the story is somebody who was actually just doing their best, your partner has a habit of narrating themselves as the only competent adult in the room. That will not change once you sign.
Question five. What will you do when you disagree with me and you are the one who is wrong
The wording is deliberate. Not what do you do when we disagree. What do you do when you are the wrong one. If they cannot picture themselves being the wrong one, you have your answer. You are signing with somebody who is going to double down on every mistake, and you are going to spend the next decade trying to help them see something they refuse to see. Don't sign that partnership.
Question six. What would you fire me for
Most partners have never let themselves think about this out loud. Once they do, the list is usually short and specific. If their list is vague, they have not thought hard enough. If their list is long, they have already been drafting the memo in their head for a while. If their list is exactly what your list would be if the question were reversed, you might have a real partner.
Question seven. What do you personally owe, to whom, and when is it due
You are entering a business partnership. Their creditors are about to become your problem in every way that matters. This is the question that surprises people most, because the honest answer includes an ex-spouse, a family loan nobody talks about, and a business obligation from a previous venture. All of those are fine. You just need to know them before you sign, not after they show up in a subpoena.
Question eight. What would make you want out of this partnership in year three
Not year one. Year three. Year one is easy because both of you are excited. Year three is when the honeymoon is over and the compounding either works or does not. If they cannot answer this question, they have not imagined the boring middle of a business, and they are going to disappear right when you need them.
Question nine. How do you behave when you are tired, and how do the people at home know you are tired
Every founder is tired eventually. The question is what you look like at that point, and whether the people you live with recognize it in time to catch you. If your partner has never noticed themselves being tired, they are going to make their worst decisions on the days they are the most tired, and they will not know they made them until the damage is done. If they have a system at home, that is a very good sign. A partner who can be caught by the people who love them is a partner you can trust with company decisions on hard weeks.
Question ten. If we sold this business in year seven, what would you do with your life the year after
You are testing whether they have a life independent of the company. If the answer is nothing specific, or a vague trip, or another company just like this one, they are going to fight the sale when it comes because their identity has fused to the business. If the answer is specific and personal, unrelated to business, that is a partner who will not sabotage a good exit because they cannot picture themselves the day after.
A few questions I almost added
The other ninety questions in the book cover a lot of ground the ten above cannot, and there were three I nearly promoted into the shortlist. The first was, how do you feel about firing a friend. That answer tells you whether your partner is going to protect a bad hire because of loyalty, or whether they can separate the person from the role. The second was, how much do you actually trust yourself under pressure. Founders who say the honest answer to this get better as partners over time. Founders who cannot answer it never get better, because they never realize where they are the weak link. The third was, what does your calendar look like when you are avoiding hard work. Every founder has an avoidance pattern. Knowing your partner's pattern in advance lets you build a company that is more resilient than the two of you would be individually.
None of these three made the shortlist because they take longer to answer well. If you have a full evening with your co-founder and you get through the ten fast, add these three. They are worth the extra hour.
How to run the conversation
Don't do this over email. Don't do this at a networking event. Do this at a table with time to spare, ideally in the evening, with something to drink and no phones on the table. Answer each one yourself first, then let them answer. Don't let anybody skip. If a question makes you both uncomfortable, that is the question that had the most to teach you. Stay in it.
If both of you can get through these ten questions honestly and still want to work together, you have earned a real conversation about equity. If either of you cannot get through them, you have just saved yourselves a decade of pain. That is what these questions are for.
The other ninety questions live in Founder Fallout. It is out now, direct on this site for twenty-four dollars and ninety-nine cents, and on Amazon in paperback and Kindle. If you are about to sign a partnership, read it together first.