What to ask a founder when you meet one
A founder in the room is a rare chance to ask what no case study contains. Better questions, grouped by topic, and a few habits that get a real answer instead of a polished one.
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Most people who get to meet a founder ask one of two questions: 'What is your advice for us?' or 'How did you become successful?' Both invite a prepared answer, and the founder gives it, politely, as they have given it before. You leave with a good mood and very little you can use.
A founder can tell you what happened in one business, in one place, over some years. That is valuable, but only if you ask for it in a form they can give. This guide groups questions by topic and adds a few habits that tend to bring out the honest version.
What you should come away with
- Ask what the founder did and saw, not what you should do
- Questions beginning 'how' and 'what was' draw out stories; 'should I' questions draw out opinions
- Ask about the unfinished parts of the business, not only the finished ones
- One founder's path is one example, so ask more than one person
- Do not ask for money, a job or a favour in the first conversation
- Follow up on what they said before moving to your next prepared question
Start with what a founder can honestly tell you. They can tell you how they started, what they tried, what went wrong, whom they hired, how they handled money and what they would change. They cannot tell you whether your idea will work, because they do not know your customer, your city or your savings. They cannot speak for every business either, because they have only seen their own corner of the market. Ask for experience and you will get something true. Ask for a verdict and you will get a guess.
Do a little homework first. Find out what the business does. If a question can be answered by a search, do not spend their time on it.
Now the questions. Here are six groups that usually work.
About the beginning. How did you start: what were you doing before, and what made you start then? Who was the first person to pay you, and how did you find them? What did you not know when you began that you now consider basic? How long before the business paid you anything?
About money. How did you pay for the first year, including your own living costs? What was the tightest month, and how did you get through it? Which customers pay late, and what do you do about it? What do you now track every week that you ignored at the start? You are not asking for private figures. You are asking how the founder thinks about money, and most are willing to say.
About selling. How do customers find you today, and was it the same at the start? What did you say in your earliest sales conversations that you would not say now? What is the most common reason people say no? How do you decide a price?
About people. Who was your first hire, and why that person? Which hire did not work, and what did you learn about hiring from it? What can you do now that you could not do when you were alone, and what do you miss?
About mistakes. What would you do differently if you started again? Which decision cost you the most, and how did you find out it was wrong? Was there a time you nearly stopped? What did you believe about the business at the start that turned out to be false? Ask kindly and listen without judging. Many founders say more than they planned to, when the question is sincere.
About what is unfinished. What are you still trying to work out? What is not working at the moment? What are you worried about? Most talks cover only what has been solved. A founder who describes a current problem, even briefly, is showing you what running a business is actually like: a series of open questions, handled one at a time.
A few habits help. Ask one question at a time and let the founder finish. If their answer opens something, follow it: 'What made that month the hardest?' is often a better second question than anything you prepared. If you are in a group, ask the question you really want answered, not the safest one.
Be careful about two things. First, avoid asking a founder for their income, their investors' terms or other private details. If they want to share, they will, and a number from one business tells you little about yours. Second, do not ask for money, a job, a referral or a partnership in the first conversation. A founder who is asked for a favour by a stranger feels used, even if they are too polite to say so. Ask for understanding first. If a relationship develops, a request may follow later and will be easier to hear.
Ask more than one person. A single founder's story is a single example, and it is shaped by the trade, the year and the city. Two or three founders from different kinds of business will disagree with each other, and the disagreement is where most of the learning is. If all of them say the same thing, treat it as a pattern worth taking seriously. If they differ, the difference tells you that the right answer depends on the business, and that you need to think about yours.
After the conversation, write down what you heard while you still remember it: three things that surprised you, one thing you will try and one question you did not get to ask. Then, within a day or two, send a short thank you, through the organiser or whatever channel you used. Say what you found useful and, later, what you did with it. 'I tried asking for a deposit the way you described' is more valuable to a founder than any compliment, because it tells them their time made a difference.