Questions to Ask an Entrepreneur
The general set, for a coffee, a networking conversation or a short mentoring call with someone who runs their own business. 60 questions that cover the whole arc at a moderate depth and get past the elevator pitch to how the work actually goes and what they have learned the expensive way. They open with the business as it runs today, then take the parts in turn: starting out, customers, pricing and cash, hiring and growth, and the personal cost, so you can pick the stretch that fits the conversation.
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The questions
Each question, and why to ask it
How do you describe what you do when someone asks at a wedding?
Why ask it
It gets you the plain version rather than the pitch, and it is an easier opening than asking about the business model. How much they simplify also tells you who their customers are.
What does a Monday actually look like for you?
Why ask it
Founders are asked about vision constantly and about their calendar almost never. The answer is usually admin, quotes, chasing payment and one thing they meant to do last week.
What were you doing before this, and what did it teach you that still applies?
Why ask it
Previous jobs supply the skill the business is quietly built on, whether that is selling, a trade, a network or knowing how a specific industry buys. It also shows whether the leap was as sudden as it sounds.
Where does your work come from now: referrals, repeat customers, advertising, cold outreach?
Why ask it
This is the answer most worth having, and most businesses are more dependent on referrals than they realise. Ask what would happen if that one source went quiet for three months.
What kind of work do you turn down?
Why ask it
Refusals show what they have learned about which customers cost more than they pay. A founder who turns nothing down is usually still in the phase of taking anything, which is its own useful data point.
What is the bottleneck right now?
Why ask it
It is a present-tense question, so you get the real state of things rather than the version on the website. Common honest answers are their own time, one supplier, cash timing, or a hire they cannot afford yet.
What was the last thing you changed your mind about in the business?
Why ask it
It shows whether they are still adjusting to evidence, and the specific reversal is usually interesting: a price, a market, a product they loved, a person. A blank answer often means a business running on habit.
How do you decide something when you cannot get enough information?
Why ask it
Everyone running a business does this weekly. Look for a practical method, a small test, a reversible version, a deadline they set for themselves, rather than a statement about trusting instinct.
What is the most expensive lesson you have paid for?
Why ask it
Money makes the answer concrete: a bad hire, an unpaid invoice, a contract signed without reading, stock nobody wanted. Ask what they do differently now, since that is the transferable part.
How do you tell the difference between a bad idea and an early one?
Why ask it
It is the hardest judgment in the job and worth asking anyone who has made it a few times. The good answers involve a signal they wait for rather than a feeling.
How do you pay yourself, and how did you land on that number?
Why ask it
Many owners take too little for too long, and hearing how they set it is more instructive than any figure about revenue. Ask when they last changed it.
Who do you call when something goes badly wrong?
Why ask it
The answer tells you what support actually exists: an accountant, a former boss, a peer group, a spouse who has heard it all. If the answer is nobody, that is often the real story of the last year.
What do you do in a month when cash is tight?
Why ask it
Practical and rarely asked. Answers include chasing invoices, delaying their own pay, a line of credit, a difficult conversation with a supplier, and each one is a technique you may need.
What part of the business would fall over if you took a month off?
Why ask it
It locates everything that lives only in their head. Owners who can answer immediately have usually tried it and found out the hard way.
What do people misunderstand about running your own thing?
Why ask it
It gives them room to correct the version they hear at parties, and the answers tend to be about freedom being smaller than expected and admin being larger. Ask what they thought before they started.
How has this changed how you spend the time you are not working?
Why ask it
It gets to cost without asking about sacrifice, which invites a rehearsed answer. Notice whether they can describe an evening or a weekend that was genuinely theirs.
Who have you learned the most from, and what did they actually do?
Why ask it
The second half matters, because most mentoring that works is specific: someone made an introduction, reviewed a contract, sat in on a call. It also shows you what useful help looks like when you go looking for it.
How do you decide to stop something you have already put a lot into?
Why ask it
Knowing when to close a product, a shop or a partnership is a skill people only learn by doing it. Ask for the last thing they stopped and how long they waited too long.
What would you be doing if you had never started this?
Why ask it
A gentle question that gets at whether the choice still feels like the right one. The answer is often more wistful than the public story allows for.
Is there anything I could help you with?
Why ask it
Almost nobody asks this and it changes the character of the meeting. Small offers are the realistic ones: an introduction, a review, a customer name, sharing something they are hiring for.
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 sign this could be a business rather than a project?
Why ask it
Founders can usually name the moment: a stranger paying, a repeat order, a waiting list. It separates the idea from the point where evidence arrived.
How did you test the idea before you built anything?
Why ask it
Look for whether money or a commitment changed hands before the product existed. Answers about positive conversations and encouraging feedback mean the idea was never really tested, only admired.
What did the first version look like, and how much of it was done by hand?
Why ask it
Early versions are usually a form, a spreadsheet and someone doing the work manually behind it. Getting this on the record stops the later product looking inevitable.
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.
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.
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.
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 did you believe at the start that turned out to be wrong?
Why ask it
Ask for the belief, not the lesson. Answers like assuming customers would care about the same feature they cared about are specific; answers about learning to persevere are a way of not answering.
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.
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.
Which piece of standard startup advice turned out to be wrong for you?
Why ask it
Gets you past the received wisdom that gets repeated on every podcast. Their disagreement is usually rooted in something concrete about their market, so ask why it did not apply rather than accepting the headline.
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.
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.
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.
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.
What does a sale leave you once delivery, fees and support are counted?
Why ask it
This separates revenue from what the business actually keeps. Founders who can answer immediately usually run tighter operations.
What does it cost you to win one customer, and how did you work that out?
Why ask it
Many small businesses have never calculated this. Either answer is informative: the number, or how they operate without it.
How many months could you run with no new sales?
Why ask it
Cash cover decides how a business behaves under pressure, more than turnover does. It also explains hiring and pricing choices.
What number do you look at first in the morning?
Why ask it
Cash, pipeline, active users, churn, or nothing at all. The choice tells you what stage the company really is at and whether the founder is running it on instrumentation or on instinct.
Who was your first hire, and what did you misjudge about hiring?
Why ask it
First hires are frequently wrong in a predictable direction: too senior, too junior, a friend, a generalist when a specialist was needed. The correction they describe is a rule you can borrow.
How do you decide whether to hire, contract out, or leave a job undone?
Why ask it
This is the recurring resourcing decision in any small business. The answer tells you how they think about fixed cost and their own time.
What do you screen for in people now that you did not know to look for then?
Why ask it
Answers get very concrete after a few bad hires: tolerance for ambiguity, willingness to write things down, how someone behaves when the brief changes. Generic answers about culture fit mean the lesson has not landed yet.
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.
What did you have to stop doing yourself, and how did handing it over go?
Why ask it
Handing over work is where most founders describe the hardest stretch of their own development. Ask how long they held on past the point they should have.
What broke first when the business grew?
Why ask it
Something always breaks: support, onboarding, cash collection, the founder. The first break shows what the company was quietly relying on.
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.
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.
How do you decide what to work on when everything looks urgent?
Why ask it
Look for a mechanism rather than an attitude: a weekly review, one metric, a rule about not starting anything new mid-month. Founders without one tend to describe their week as reactive when asked the previous question.
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.
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 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.
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.
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.
If you started again tomorrow, what would you do in a different order?
Why ask it
Better than asking what they would change, because sequencing is where most of the avoidable damage happens: hiring before revenue, building before selling, raising before knowing what to spend it on.
What part of your path should someone not copy?
Why ask it
Founders enjoy this one and it counters the tidy version of the story. It is also the most generous thing they can offer a listener.
Making a Short Conversation Count
Practical guidance for the conversation itself
Getting the meeting and keeping it useful
- Ask for something specific and small: twenty minutes on one topic, by phone, at a time that suits them. Open-ended requests to pick someone's brain are the ones that get ignored.
- Say why them. One line about what you read, bought or noticed does more than three paragraphs about yourself.
- Put your actual question in the request. It lets them answer usefully rather than arriving to a general conversation.
- Turn up with two questions, not twenty. Depth on two beats a survey of everything.
- Watch the clock and offer to stop on time. The person who ends the call at twenty minutes is the person who gets a second call.
- Do not use it as a pitch. If you want to sell them something, that is a different meeting and it should be asked for as one.
Follow-up questions that open an answer up
- What happened next. The consequence is nearly always more useful than the decision.
- How did you find that out. It gets you the method rather than the conclusion.
- What would you do with my constraints. It stops advice that assumes their contacts and their capital.
- Can you give me an example from this year. Recent examples are truer than career-defining ones.
- What did that cost. Time, money, a relationship, a customer. It gives scale to the story.
What not to expect from them
They cannot tell you whether your idea will work
Nobody can, and asking pushes them into either flattery or a discouraging guess. Ask what they would test first and how they would test it cheaply.
Introductions are earned, not requested at the first meeting
Their contacts are their reputation. Do the thing they suggested, tell them the outcome, and the introduction often follows without being asked for.
Free consulting has a limit
Reviewing your plan, sitting on your calls, or making your spreadsheet work is paid work. Ask what they charge if that is what you want.
Their answers describe their market and their moment
Costs, competition, platforms and rules change. Treat what they say as one data point and get a second conversation with someone in a different position.
Afterwards
- Send a short thank you the same day, naming the one thing you are going to act on.
- Do that thing, then report back within a month with what happened, including if it did not work. This is the entire difference between a contact and a relationship.
- Keep your notes in one place with the date. Advice from three founders reads differently side by side, and the contradictions are informative.
- Pass something back when you can: a customer, a candidate, an article about their sector, a genuine referral.
- Do not forward their private numbers or stories to anyone. Word travels in small industries faster than anything you would gain.