100 Questions to Ask an Entrepreneur
The full reference, meant for picking from rather than working through. One hundred questions grouped by theme, from easy openers through money, pricing, customers, hiring and the personal cost, so you can assemble a set that fits whatever conversation you are actually having. For a session you can run start to finish in about an hour, the 50 questions to ask an entrepreneur set is ordered as a single interview.
The questions
Open any question for the note
What does the company actually do, in the words you would use with a stranger at a bus stop?
Why ask it
Founders default to the investor version, which is fluent and tells you nothing. The plain version shows whether they know who the customer is, and any hesitation here is usually a positioning problem inside the company too.
What were you doing in the year before you started?
Why ask it
The year before tells you what the business is a reaction to: a boss, a redundancy, a problem at a previous job, a bit of luck. It also sets the reader up to understand the risk they took.
Whose problem were you trying to solve, and did you have it yourself?
Why ask it
Founders who had the problem talk about it in the first person and with irritation. Founders who spotted it as an opportunity describe a market, and that difference explains a lot of what happens later.
What was the first version of the product, and how bad was it?
Why ask it
Almost everyone starts with something embarrassing, and saying so is the fastest way to establish that this is a real conversation. Ask what it could not do, because that is where you learn what was optional.
How did you get your very first paying customer?
Why ask it
The first sale is almost never repeatable, which is exactly why it is worth hearing. A friend, an ex-colleague, a cold call at a conference: it tells you whose trust they started with.
How much money did you start with, and where did it come from?
Why ask it
Savings, a redundancy payment, a parent, a credit card, or a partner's salary each change the story completely. Founders often skip this, and skipping it is how survival gets mistaken for genius.
Did you keep another job while building this, and for how long?
Why ask it
The overlap period is the practical detail aspiring founders most want and most rarely get. It also tells you how long the business took to pay a wage, which is a better milestone than a launch date.
How did you land on the name?
Why ask it
A light question that reliably produces a story, and a useful one to place early while people are settling in. What was rejected often reveals what the company thought it was going to be.
Did you have a cofounder, and how did you decide who owned what?
Why ask it
Equity conversations are remembered in detail because they are uncomfortable. Whether it was split evenly, negotiated, or never discussed properly predicts most cofounder trouble that follows.
Who told you not to do it, and what was their argument?
Why ask it
The strongest objection is often the one that later turned out to be half right. Ask what part of the warning proved accurate, and you get a much better answer than a story about doubters being wrong.
What did the first ten customers have in common?
Why ask it
This is where a real market either appears or does not. Founders who cannot describe a pattern usually spent the next two years selling to anyone who would listen.
What did you believe in the first six months that turned out to be wrong?
Why ask it
Every founder has one of these and most enjoy telling it, because it is safely in the past. The value is in what evidence changed their mind and how long they resisted it.
What was the closest you came to running out of money?
Why ask it
Ask for the month and the balance. A specific near-death story is where you find out who they borrowed from, what they stopped paying, and what they were willing to do to survive.
What did you cut when cash was tight, and what did you refuse to cut?
Why ask it
The refusal is the interesting half. Whatever a founder protects when there is no money left is what they genuinely believe the business is, whatever the strategy documents say.
Which month was the worst, and what happened in it?
Why ask it
Anchoring to one month gets you a scene rather than a summary. It also tends to surface the events founders leave out of the public story, such as a lost customer or a cofounder leaving.
What did you get wrong about how long things would take?
Why ask it
Almost every founder underestimates by a factor they can still quote. The useful part is which activity was slowest: hiring, sales cycles, regulatory approval, or building the thing itself.
What was the first thing you built that nobody wanted?
Why ask it
A concrete failure question that is easy to answer because the product, not the person, is the subject. Ask how long they kept selling it after they knew.
When did you first pay yourself, and how did you set the number?
Why ask it
Founder pay is a taboo that hides real information about the company's health and about their personal risk. It is also the single most practical figure for anyone considering the same path.
What did you personally put at risk?
Why ask it
A house, a pension, a personal guarantee, or nothing at all. This is the difference between an entrepreneur with a safety net and one without, and it changes how their advice should be read.
Was there a moment you decided to quit, and what happened next?
Why ask it
Most founders have had at least one day where they had made the decision. What pulled them back, an email, a payment, a conversation, is usually the most human material in the interview.
Who helped you at a point where they did not have to, and have you told them?
Why ask it
This gets a name and a specific favour rather than a general nod to supporters. It also tends to be the question that changes the tone of the whole conversation.
What did you learn about your own limits in the first two years?
Why ask it
Founders answer this with either a capacity they discovered or a breakdown they downplayed. Either is honest information about what the work costs.
What did you have to unlearn from your previous job?
Why ask it
Habits from a large company, from consulting, or from academia all break in a small business in different ways. This question flatters and informs at the same time, which makes it a reliable one.
What advice did you follow that turned out to be wrong for your business?
Why ask it
Bad advice usually came from someone credible, which is what made it dangerous. Ask why it did not fit, and you learn what is genuinely specific about their market.
How do you find out what customers want, beyond asking them directly?
Why ask it
Anyone can say they talk to customers. What separates founders is the mechanism: support tickets read personally, sales calls recorded, churn interviews, or watching people use the product.
What is the most common reason people say no?
Why ask it
The top objection is memorised in any company that sells, so a vague answer suggests the founder is not close to sales any more. The specific answer tells you the market's real hesitation.
Which customer complaint changed the product?
Why ask it
This is a much better question than asking about feedback, because it forces one traceable outcome. If nothing comes to mind, the feedback loop is decoration.
What do customers use it for that you never intended?
Why ask it
Unintended uses are often where the next business is. Founders usually know one and rarely get asked, so this question tends to produce genuinely fresh material.
How did you set your first price, and what happened the first time you raised it?
Why ask it
Pricing stories are concrete and nearly always undersold at the start. Watch for how much revenue they left on the table for how long, and what finally forced the change.
Which feature took the most work for the least return?
Why ask it
Sunk-cost stories are specific and useful, and they usually reveal who inside the company pushed for it. Ask what they would have built instead with the same three months.
How do you decide what not to build?
Why ask it
Any founder can list priorities. The test is whether they can describe an actual process: a rule, a person who says no, a threshold of customer requests before anything gets made.
What is the honest reason customers leave?
Why ask it
The stated reason in a cancellation form is rarely the real one. Founders who have gone and asked leavers directly can tell you, and those who have not will answer with price.
Who is your product wrong for, and do you tell them so?
Why ask it
A founder who cannot name a poor-fit customer is either very early or losing money on support. Turning business away is one of the clearest signs a company understands its own economics.
What have you learned about how buyers in your market actually decide?
Why ask it
Who signs, who blocks, and what triggers a purchase is hard-won knowledge and usually contradicts the founder's original assumption. This is often the most reusable answer in the whole interview.
Which channel brings customers who stay, and which brings ones who leave quickly?
Why ask it
Splitting by retention rather than volume separates real marketing knowledge from dashboard talk. The bad channel is often one they are still spending on.
What was the first marketing that actually worked?
Why ask it
Ask for the first thing rather than the current stack, because early wins are cheap and repeatable and current strategy is usually a budget. Expect something unglamorous like a forum post or a single event.
What is the smallest change you made that had the largest effect on revenue?
Why ask it
Founders remember these precisely because they felt like cheating: a headline rewritten, a form field removed, one follow-up email added. It is usually the most immediately borrowable answer in the interview.
What do you understand about your market that competitors seem not to?
Why ask it
This invites a boast, and the answer is worth having anyway, because you learn what they think their edge is. Follow it with a request for evidence and see whether it holds.
Did you raise outside money, and what did you give up?
Why ask it
The answer is never only equity: board seats, reporting, a growth rate they now have to hit. Founders will often describe the terms freely once you ask what changed rather than how much they raised.
What did an investor ask that you could not answer?
Why ask it
Fundraising exposes gaps in a founder's own understanding of the business. The question they fumbled is usually the metric they then went and learned properly.
If you did not raise money, what did that cost you?
Why ask it
Bootstrapped founders tend to be evangelical, so asking about the cost rather than the benefit produces the balanced version: slower hiring, a lost market window, years of thin pay.
How do you know week to week whether the business is healthy?
Why ask it
You are looking for two or three numbers, not a dashboard tour. Founders who cannot name them either delegate finance entirely or are avoiding it.
What number do you look at first in the morning?
Why ask it
The habitual number reveals what they are actually managing: cash, bookings, signups, or a vanity figure. It also makes a good, quotable answer.
What are your margins, and how have they moved since the early days?
Why ask it
Direction matters more than the figure. Margins that fell as the company grew usually mean the sales model or the support burden changed shape and nobody adjusted pricing.
How long could the business survive with no new sales?
Why ask it
Founders know this number precisely, and hearing it puts everything else in proportion. Ask what they did the last time it got uncomfortably short.
What was your worst spending decision?
Why ask it
Expect an office, a rebrand, a conference stand, or a piece of software nobody used. The pattern in these stories is nearly always spending in anticipation of growth that had not arrived.
How do you decide whether to hire someone or wait?
Why ask it
This is where discipline shows. Look for a trigger, such as a workload they can measure or revenue per head, rather than a feeling that everyone is stretched.
What have you learned about getting customers to pay on time?
Why ask it
Late payment is an unglamorous topic that founders have strong, practical views about. The answers, deposits, stage payments, stopping work, are immediately useful to anyone running a small business.
How do you think about debt?
Why ask it
Attitudes to borrowing are usually inherited rather than reasoned, and founders will often say so if you ask where the view came from. It also predicts how they will behave in the next downturn.
What does your accountant or finance person tell you that you resist?
Why ask it
This surfaces a live disagreement rather than a settled lesson. It is also one of the few questions that reliably gets a founder to describe their own bias.
Have you ever had to delay payroll, and how did you handle it?
Why ask it
A hard question, so ask it late. How they told the team, or whether they told the team, is a more accurate account of their leadership than any answer about culture.
What would you do differently about pricing if you started again?
Why ask it
Nearly every founder says they would charge more, so push for the mechanism: charge whom, for what, and how they would have known. That is where the transferable lesson lives.
Who was your first hire, and what did you get wrong in that process?
Why ask it
First hires are made on instinct and remembered vividly. Whether they hired a friend, a specialist, or someone to do the work they disliked tells you what they thought the bottleneck was.
What is one interview question you always ask, and what are you listening for?
Why ask it
This gives you something concrete and quotable, and it shows whether their hiring is a system or a vibe. Ask for an answer that made them say no.
Who has been the hardest person to replace?
Why ask it
The answer is often not the most senior person but the one who held undocumented knowledge. It quietly reveals how dependent the company is on individuals.
What did you learn from firing someone?
Why ask it
Most founders wait too long and can tell you exactly what it cost the team. Ask how long they knew before they acted, and the answer is usually months.
How do you tell someone their work is not good enough?
Why ask it
The words people actually use are far more interesting than a philosophy of feedback. Founders who cannot describe the conversation probably avoid having it.
What do you do when a good person wants to leave?
Why ask it
Whether they counter-offer, ask what would change their mind, or let them go cleanly says a lot about how they see staff. Ask about the last time it happened rather than the policy.
What do you delegate now that you swore you never would?
Why ask it
This charts the founder's own development in a way that a question about growth cannot. The last thing they let go of is usually sales, product detail, or the company's public voice.
What still lands on your desk that should not?
Why ask it
Most founders can name one immediately and already know it is a problem. It is frequently the same thing that is holding the company at its current size.
How do you decide what to pay people, and how open are you about it?
Why ask it
Pay transparency splits founders sharply, and the reasoning is revealing either way. Ask what happened the last time someone found out what a colleague earned.
What do you want people to say about working here after they leave?
Why ask it
This gets past culture slogans, because leavers are honest and founders know it. The gap between the hoped-for answer and what leavers actually say is the real culture question.
What behavior would you not tolerate whatever the results?
Why ask it
A founder who cannot name one has not been tested yet or has already made the compromise. The specific answer is usually traceable to somebody they once employed.
How has your management changed since the company passed ten people?
Why ask it
Ten and then thirty are the two points where founders stop being able to hold everything in their head. Ask what broke first, because it is nearly always communication or hiring standards.
What do you do about a high performer who upsets everyone around them?
Why ask it
This question forces a real trade-off rather than a value statement. The story of the last one, and whether they kept them, tells you what the company actually rewards.
What is the most useful thing an employee has told you to your face?
Why ask it
This asks a founder to credit somebody who criticised them, which not everyone can do. If nothing comes to mind, that is information about how safe it feels to speak up there.
Which decision took you longest, and what finally settled it?
Why ask it
The deciding factor is the interesting part: a deadline, a person leaving, running out of money, or somebody else making the choice for them. Founders rarely decide the way strategy books describe.
What did you say no to that you still think about?
Why ask it
The path not taken is easier to discuss honestly than a mistake, and it usually reveals what they are still ambivalent about. Ask whether the offer could come back.
What has a competitor done that you wish you had done?
Why ask it
This is a generous question that gets specific answers, and it tells you who they actually watch. Vague dismissal of all competitors usually means they are not watching anybody.
How do you tell the difference between a bad month and a real signal?
Why ask it
This is the central judgment of running a business and most founders have a rule of thumb. Ask about the last time they got it wrong in each direction.
What have you copied from another company, and did it fit?
Why ask it
Imported practices, from performance reviews to sales methods, often break in a smaller company. The story of a borrowed system that failed is more instructive than one that worked.
What are you betting on about the next three years?
Why ask it
You want the assumption underneath the plan rather than the plan. A founder who cannot state a bet is running the company on momentum.
What could kill this business?
Why ask it
Most founders answer honestly if you ask plainly, and the answer is rarely a competitor. Regulation, one large customer, a platform they depend on, or their own health come up more often.
If you had to shut down one part of the business, which would it be?
Why ask it
Forcing a choice surfaces the part they already suspect is not working. It is also the question that most often produces news.
If a year's revenue arrived tomorrow with no strings, what would you do with it?
Why ask it
A hypothetical that reveals real priorities: hiring, paying down debt, buying time, or paying themselves. The answer often contradicts the strategy they described earlier.
What has been on your list for a year without getting done?
Why ask it
The perpetually postponed item is usually either unimportant or the most important thing in the company. Asking which of those it is makes for an uncomfortable and useful moment.
If you had to double the business without hiring anyone, how would you do it?
Why ask it
The constraint forces them past the standard answer of more salespeople. Pricing, retention, and automation are where the thinking goes, and it exposes what they already know is inefficient.
What would make you sell?
Why ask it
Even founders who say never have a number or a condition, often about their family or their health. Asked calmly, this is one of the most revealing questions available.
What does an ordinary Tuesday look like, hour by hour?
Why ask it
Specificity is the whole point. Founders describe their week in aspirational terms until you make them account for the hours, and then the meetings and the interruptions appear.
What is the first thing you do when you start work?
Why ask it
A small, concrete habit that makes a good detail and reveals what they consider urgent. Founders who begin with other people's messages tend to run the whole day reactively.
What have you given up that you did not expect to give up?
Why ask it
The unexpected losses, a sport, a friendship group, a language, an instrument, are more honest than the standard sacrifice narrative and more memorable to read.
How has this affected the people who live with you?
Why ask it
Founders answer this more openly than expected if you ask about others rather than themselves. It is also the part of the story that is almost always missing from public accounts.
What do you do when you cannot sleep because of work?
Why ask it
A specific, physical question that gets past resilience talk. Whether they get up and work, wake a cofounder, or lie there is a fair proxy for how they carry pressure.
Who can you speak to honestly about the business?
Why ask it
Founders often name one person, and sometimes nobody. If the answer is a spouse alone, that is worth exploring, because it is a heavy load to place on one relationship.
When did you last take a full week off, and what happened while you were gone?
Why ask it
This tests whether the company can run without them, which is the real measure of what they have built. What broke in that week is usually where the next hire belongs.
How do you tell burnout apart from being tired?
Why ask it
Anyone who has been through it has a marker: losing interest in the parts they used to enjoy, or dreading a specific meeting. Their answer is practical help for the reader.
What do you spend money on now that you would not have before?
Why ask it
Small, concrete, and revealing about what they came to value: cleaning, flights, time, help at home. It also shows what running a business taught them about their own hours.
Which part of the job do you dislike and still do yourself?
Why ask it
This locates the gap between what they enjoy and what only they can do. It is frequently finance, recruitment, or firing people, and it explains where the company is slow.
What do you say at a party when someone asks what you do?
Why ask it
The social answer is shorter and more honest than the professional one, and it shows how they think about their own status. It is also a reliable source of a good closing line.
What would you be doing if this had not worked?
Why ask it
Founders have usually thought about this in detail during a bad month. The alternative life tells you what they think they are good at when the company is stripped away.
What did success turn out to feel like?
Why ask it
The gap between the imagined version and the actual one is where the honest answers live. Expect anticlimax, and expect it to be the part readers remember.
What do you know now that would have saved you two years?
Why ask it
Putting a time cost on the lesson forces them past general wisdom to one specific thing. If the answer is about people rather than product, ask what they would have done differently in hiring.
What advice do people give founders that you think is wrong?
Why ask it
Contrarian questions get lively answers and reveal what they have tested themselves. Follow up by asking for whom the standard advice does work, so the answer stays useful.
Which of your early decisions has held up best?
Why ask it
Founders talk far more readily about mistakes than about durable choices, so this often needs a moment. A name, a pricing model, or a decision not to raise money are common answers.
What are you still bad at?
Why ask it
Asking about the present tense rather than the past prevents a tidy redemption story. A founder who claims nothing here is not being useful to you.
Who deserves credit for this that never gets any?
Why ask it
This reliably produces a name that has appeared nowhere else, often a first employee, a spouse, or an early customer. It is a generous question and it tends to open people up.
What do you want the company to be when you are no longer running it?
Why ask it
Succession is a subject founders avoid publicly and have thought about privately. The answer separates people building a business from people building a job for themselves.
How will you know when it is time to stop?
Why ask it
A quieter version of asking what would make them sell, and it usually gets a more personal answer about age, health, or the point at which the work stops teaching them anything.
What question do interviewers always ask that you are tired of?
Why ask it
Useful for you and flattering to them, and it usually tells you which parts of the public story they no longer believe. It also warns you off the ground everyone else covers.
What should I have asked you?
Why ask it
Ask this last, always. Founders use it to raise the thing they came to say, and the final two minutes of an interview are often where the best material arrives.
Interviewing a Founder
Practical guidance for the conversation itself
Before the Interview
Learn the business model, not just the story
Know roughly how they make money, what they charge, and who they compete with. Founders answer generic questions generically, and the conversation only becomes interesting once they can tell you are past the basics.
Read the most recent thing they said in public
A talk, a post, or a funding announcement gives you the version they are currently telling. Your best questions are usually the gaps in that version rather than the subjects it covers.
Decide whether you want the story or the mechanics
Origin stories are polished and easy to get. Numbers, pricing, and hiring mistakes take longer to reach and are what most audiences actually want, so put those early while attention is high.
Ask for a length and finish inside it
Request the time you need, then end a few minutes early. Founders remember who ran over, and finishing early is the most reliable way to be given a second conversation.
Getting Past the Pitch
- If they will not give absolute numbers, ask for ratios or ranges. Many founders will say margin is about a third even when they will not name revenue.
- When an answer sounds rehearsed, ask what happened in a specific month rather than in general. Dates break scripts.
- Ask about a failure immediately after they describe a success. The contrast gets answered when a standalone question about failure gets deflected.
- Follow the money and the people. Cash and hiring are where real decisions show up, and they are harder to narrate heroically than product decisions.
- Do not let hindsight pass as strategy. Ask what they believed at the time and what they would have bet on then.
- Let a silence run after an uncomfortable answer. Founders are practiced talkers and will usually fill it with something better than your next question.
- Keep the last two minutes for an open handover. What should I have asked is where interviews tend to produce their best material.
If You Are Thinking of Starting Something Yourself
- Ask about the first two years, not the current business. Advice from their present stage rarely transfers to a company with no customers.
- Ask what they would do again and what they got away with. Survivors often describe luck as judgment, and the difference matters a great deal to you.
- Ask what the business cost them personally and take the answer at face value rather than as modesty.
- Ask for the names of two people who tried something similar and stopped, then go and speak to them. It is the most useful follow-up available and almost nobody does it.
- Ask what they would charge for an hour of their time now. It calibrates the advice you are getting for nothing.