Best Questions to Ask an Entrepreneur
For the twenty minutes you get with a founder who has told their story many times before. These are the questions that have no rehearsed answer, aimed at the month the money ran short, the hires and failures they do not put in the talk, and what they would do differently. If you are meeting for the first time and want something easier to answer, the good questions set is gentler ground.
The questions
Open any question for the note
What is in the version of this story you tell on stage that you would leave out here?
Why ask it
Founders know their own polished version better than anyone and most enjoy being let out of it. Whatever they leave out is usually where the interesting material starts.
Who was your first paying customer, and how did you find them?
Why ask it
Almost always someone they already knew, which is worth hearing because it contradicts the idea that businesses begin with marketing. If they cannot remember the first customer, they may be a founder who joined after the early period, which changes what else to ask.
What did you charge at the beginning, and how did you pick the number?
Why ask it
Nearly every founder underpriced at the start and can tell you what it cost them. The story of how the price changed, and how the first customer reacted, is the most transferable piece of advice in most of these conversations.
How did you pay your rent in the first year?
Why ask it
Savings, a partner's income, contract work on the side: each answer changes what their risk actually was. It also quietly corrects stories that skip the funding of the founder themselves.
What's the closest you came to shutting it down?
Why ask it
Every business that lasted has a near-death moment, and this is the question that gets it. Watch whether they can name the month. Founders who describe the near-miss in detail tend to be the ones telling you the truth about the rest of it too.
Was there a point where you couldn't cover payroll or a bill, and what did you do?
Why ask it
The specifics are what matter: whose invoice they delayed, which credit line they used, whether they told the team. It also reveals how they treat people when the money is short, which is the most reliable read on a founder's character you will get.
What did you build that nobody wanted, and how long did you keep pushing it?
Why ask it
The wasted build is common, but the length of time they defended it is the part rarely admitted. That number says more about their judgement than the mistake does.
Which customer did you turn away, and what did it cost you?
Why ask it
Saying no to revenue is the hardest discipline in a young business. If they cannot think of an example, they probably said yes to everything, which explains a lot about how the company has ended up shaped.
Who was your first hire, and would you make that hire again?
Why ask it
The second half turns a fact into a judgment. Founders often admit the first hire was a friend, or filled the founder's own strongest skill rather than their weakest, and both mistakes are common enough to be worth hearing described.
What's the hardest conversation you've had with someone who worked for you?
Why ask it
Firing someone, missing a promotion promise, or telling a team the money is running out. How they narrate it, whether they take responsibility or describe it as unavoidable, tells you more than any question about leadership style.
How did you and your co-founder divide things up, and how did that hold up?
Why ask it
Splits made in week one rarely survive year three, and the friction usually appears where responsibilities overlapped rather than where they were separate. If there was no co-founder, ask who they went to when they were stuck, which uncovers the same thing.
What were you still doing yourself a year after you should have stopped?
Why ask it
This asks for a specific failure of delegation with a timescale attached. Most founders have one they are still slightly embarrassed about.
What decision did you put off, and what did the delay cost?
Why ask it
Delay is the most common and least discussed founder mistake, and it is usually about a person rather than a strategy. Asking for the cost turns the answer from a reflection into something concrete you can learn from.
How do you decide whether to spend money now or wait?
Why ask it
You want the actual test they use, not a philosophy: does it pay back within a quarter, does it reduce a risk, would they regret it if revenue halved. Founders who cannot describe a test are usually deciding by mood, and their spending shows it.
How did you fund it, and would you fund it that way again?
Why ask it
Bootstrapping, a loan, friends and family, or investors all shape what a company is allowed to become. The second half often produces the most honest sentence of the conversation, especially from founders who raised money early and lost some control of the pace.
What does a bad week look like now, and how often do they come round?
Why ask it
A founder three years in has a different bad week from one in month six. The frequency is the honest measure of whether the business has settled.
What has this cost you outside work?
Why ask it
Ask it plainly and leave the silence. Most founders will name a relationship, their health, or years they did not spend somewhere else. It is the question they are least often asked and often the one they most want to answer honestly.
What do you know now that would have made the first two years shorter?
Why ask it
More useful than asking what they would do differently, because it forces a specific piece of knowledge rather than a wish. Answers tend to be unglamorous: charge more, hire slower, talk to customers before building anything.
What do you tell people who ask you for advice that you know they will ignore?
Why ask it
This gets past the general encouragement founders usually give. The advice nobody takes tends to be the advice that cost them the most to learn.
If you sold it or closed it tomorrow, what would you miss?
Why ask it
The closing question. Answers about the people or about solving problems all day describe someone who would start again; answers about status or the idea of being a founder describe someone who might be ready to stop and does not yet know it.
How to use these questions
Practical guidance for the conversation itself
Getting past the version they usually tell
Ask for a month, not a phase
Founders have a rehearsed narrative in three acts. Anchoring a question to a specific period, the month before they started, the week they nearly ran out, breaks the script and produces detail they have not smoothed over yet.
Ask what it cost, every time
Any decision they describe becomes useful the moment you ask what it cost: in money, in time, in someone leaving. Without that, you get a set of principles that sound good and cannot be acted on.
Do your homework so you don't waste the slot
Read their website, their last few interviews and whatever they have published. If you know the funding history and the product line, you can spend the whole conversation on the parts nobody has asked about.
Let the silence sit
The best answers on this page come after a pause, particularly the questions about cost, near-failure and hard conversations. Filling the gap with a follow-up is the most common way to lose the answer you were about to get.
Choosing questions for the setting
Coffee or a favour of their time
You have twenty to thirty minutes and they are doing you a kindness. Pick three questions relevant to a decision you are actually facing, say what the decision is, and stop on time. Founders answer far more openly when a question is tied to something specific in front of you.
Podcast or recorded interview
Open with the first customer and the first price, since those are concrete and get the guest talking. Save the near-death and the personal cost questions for the second half, once they have relaxed into it, and be prepared to cut anything they later regret.
Panel or public stage
Avoid anything that requires them to disclose numbers, name a customer or discuss a co-founder dispute in front of an audience. The delay question, the pricing question and what would have made the first two years shorter all work well in public.
A small business owner rather than a startup founder
Skip the funding and scaling framing entirely. Ask about the first customer, pricing, the bad month, hiring, and what they still do themselves. Those are the questions that describe running a shop, a studio or a practice, and they get better answers than anything borrowed from startup language.
What tends to go wrong
Pitching instead of asking
Describing your own idea and waiting for approval is the most common way these conversations get wasted. If you want feedback on something specific, ask for it directly and briefly, at the end, after you have listened.
Asking for money or an introduction on first contact
Both are reasonable requests eventually and both end a first conversation early. If you want an introduction later, earn it by being useful and by following up on what they suggested.
Asking about revenue in the wrong setting
Many founders will discuss numbers privately and none want to in front of a room. If the number matters to your question, ask about direction and shape instead: growing, flat, seasonal, dependent on one client.
Treating survival as proof of method
A founder who succeeded once can tell you what happened to them, not what will happen to you. Ask what they think was luck, which most honest founders will answer generously, and weigh the rest of the advice accordingly.
Follow-ups worth keeping ready
- "How long did it take you to see that?" separates hindsight from judgment at the time.
- "Who told you, and did you believe them?" often uncovers the advisor or the customer who changed their mind.
- "What would you have needed to know to decide sooner?" is the practical version of any regret.
- "How much of that was luck?" tends to get a more honest answer than expected.
- "What did that do to your cash?" turns a story about strategy into a story about the business.