Questions to Ask Successful Entrepreneurs
The best questions to ask successful entrepreneurs are the specific ones: where the first customer came from, how long it took before the business paid a salary, how much of it came down to luck. Here are 60 questions for a coffee, a panel, a mentoring session or a class assignment that asks you to interview a founder, in six groups: starting out, money, risk and setbacks, people, running the business, and lessons and advice. The staples are all here, from how they came up with the idea to what they would tell someone just starting, and each has a note on getting past the practised answer, what a good reply sounds like or what to ask next.
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The questions
Each question, and why to ask it
Starting out
How did you come up with the idea for your business?
Why ask it
The standard opener, and worth asking because the honest answer is seldom a flash of inspiration. It tends to be a job they held, a problem that kept annoying them or a customer who asked for something. Follow up with how far the business has moved from that first idea.
What made you start your own business instead of staying in a job?
Why ask it
Listen for whether they were pulled toward something or pushed out of something: a layoff, a bad boss, a ceiling on pay. Both are respectable, and the pushed version tends to get trimmed when the story is told on a stage. Notice which of their reasons are also yours.
Where did the first paying customer come from?
Why ask it
Expect a person and not a marketing channel: a former colleague, a neighbour, someone who owed them a favour. That is a useful correction if you have been picturing a launch day. Find out what was actually sold, since a first sale can be a service or a promise and not the product the company is known for now.
How did you fund the business in its first year?
Why ask it
Savings, a loan, a partner's income, a client who paid up front and outside investors each put different limits on a company. Ask what the money went on and what the arrangement cost them in control or in sleep. Terms for loans and investment vary by country and lender, so take the figures as their story and not as a guide to yours.
How did you know it was time to leave your job and do this full time?
Why ask it
Some set a threshold, such as a month of revenue matching the old pay or a year of living costs saved, and some had the choice made for them. A threshold is a rule you can adapt to your own bills. The follow-up is how long they ran the two side by side before choosing.
What did your life look like in the twelve months before you started?
Why ask it
Origin stories usually begin at the founding, which skips the part you can learn from. That year holds the savings, the job that paid for it, the contacts and the frustration that supplied the idea. It also puts a realistic timeline on what looks, from this distance, like a single decision.
Did you write a business plan, and how much of it survived?
Why ask it
A good-humoured way to find out how they planned. You may hear that the document was written for a bank or a landlord and was out of date within months. If the list of costs held up and the sales forecast did not, that tells you which half of your own plan to trust.
Who told you not to do it?
Why ask it
There is usually a name, and often it belongs to someone whose opinion mattered to them. What was the objection, and did it turn out to be right? The honest answer is sometimes partly yes, which is why this gets further than a question about doubters in general.
What did the first year actually look like, month to month?
Why ask it
Founders tend to describe the early years in summary, and the summary skips the long flat stretch. Going through it in order brings out how many months passed without revenue and what they lived on in the meantime.
When did you first believe the business would survive, and what had changed?
Why ask it
You are after a turning point with a date on it: a contract signed, a hire, a change in price. If nothing in particular changed, the growth may owe more to timing than to a decision, and that is worth knowing before you copy the method.
What did you have going for you at the start that not everyone has?
Why ask it
Savings, a partner's income, a degree that opened doors, a family business, contacts from an earlier job. Knowing where they started is what makes their advice usable, because you can adjust for the difference. Say it plainly and without an edge, so it lands as curiosity and not as an accusation.
Money
How long was it before the business paid you a normal salary?
Why ask it
A number worth having, and one that rarely gets volunteered. It sets a realistic length for the lean period and leads into how they covered rent and food in the meantime, which is the worry underneath most hesitation about starting anything.
How did you work out what to charge?
Why ask it
Many owners say they started too low, and the story of the first price rise tends to be short and instructive. Ask who they compared themselves with and whether any customers left when the price went up. If they still charge the opening price, ask what is stopping them.
What early expense would you skip if you were doing it over?
Why ask it
The answers are concrete and a little funny: the office taken too soon, the rebrand, the conference stand, the developer hired before there was work for them. Listen for what sat behind the purchase. Often it was a wish to look like a real company before there was anything to sell.
What did you do when you nearly ran out of money?
Why ask it
Plenty of businesses have a month like this, and the detail is the education: who they called, what they cut, which bills they delayed, whether they told the team. If they say it never happened, check whether that counts the stretch before any money was coming in at all.
What did you do with the first real profit?
Why ask it
Put back in, paid out or parked as a cushion: the choice shows what they were afraid of at the time. A founder who built a reserve first may have a cash scare behind them. It is also a polite way to learn when profit actually arrived.
Which numbers do you look at every week?
Why ask it
The short list shows what the business runs on: cash in the bank, repeat orders, enquiries, how long a job takes. If you get a dozen, ask which one they would keep if they could keep only one. A good second question is which number they stopped watching, and why it turned out not to matter.
What did nobody warn you about on the paperwork side, like tax, contracts or insurance?
Why ask it
Expect a story about a bill that arrived at the wrong moment or a handshake deal that should have been on paper. The rules differ by country, state and type of company, so treat the answer as a list of things to raise with an accountant or lawyer where you live, not as the rules themselves.
Risk and setbacks
What did you get wrong about the market at the start?
Why ask it
An easy one for someone who has done well, because the error is safely behind them. It may have been about the customer, the price or how fast people would switch, and each points to different homework for you. If they say they had it right from day one, try asking what surprised them instead.
What is the biggest challenge you have faced in the business?
Why ask it
Broad on purpose, because what they choose is the information. A difficult partner, a legal dispute, a product that flopped and a lost customer are very different kinds of hard. Once they have picked, narrow it at once: what did the worst week of that look like?
Which failure taught you the most?
Why ask it
People who have done well tend to keep one polished failure for interviews, the kind that ends in a lesson and a win. Thank them for it, then ask for one that still stings. The second answer is often smaller, more recent and more useful.
How did you get used to hearing no?
Why ask it
Selling, raising money and hiring all come with a steady run of refusals, and nobody starts out comfortable with it. Some keep count, some make a game of it, and some never adjusted and hired a salesperson instead. Whichever it was, you learn what the early months of asking really felt like.
Which decision took you longest, and what finally settled it?
Why ask it
What settled it is the interesting half: a customer's reaction, a number crossing a line, a deadline, one person's advice. That shows how they decide when the facts run out, and it is easier to borrow than a principle. See whether they think they would decide faster now.
How do you decide whether a risk is worth taking?
Why ask it
From the outside entrepreneurs can look like gamblers, and many will tell you they are the opposite. Ask about one real bet and how they limited what they could lose: a trial run, a cap on spending, a way back. If the answer is that they trust their gut, ask about a time the gut was wrong.
How did you know when to change direction and when to keep going?
Why ask it
There is no clean rule, so ask for the case. What evidence made them drop a product, a market or a plan, and how long had they been ignoring it? Stubbornness and persistence look the same until afterwards, and an honest founder will say so.
Was there a point when you nearly gave up, and what kept you going?
Why ask it
Leave a pause after this one. The reason they stayed is often unheroic: a lease, staff who depended on the wages, nothing else to go back to. That can be more reassuring to hear than a speech about passion.
How do you handle the stress when things are going badly?
Why ask it
You want what they actually do in a bad week, not what they would recommend: a run, a call to one particular person, a rule about no email after nine. Some will say they handled it poorly for years. If they mention a doctor or a counsellor, take that as trust and do not dig.
People
What did you learn from your first hire?
Why ask it
First-hire stories tend to be candid, because the mistakes were small enough to admit and large enough to remember. Ask what they would do differently, and whether the person is still there. How they talk about someone who left tells you as much as the lesson itself.
What do you look for in a new hire these days?
Why ask it
Set beside the first-hire story, this shows how their judgement has moved. Push for something you could observe in an interview, such as how a candidate describes a job that went badly. "Attitude" and "fit" are labels, so ask what they look like on an ordinary Tuesday.
Which part of the business did you hold on to for too long?
Why ask it
Sales, the product, hiring, the books: there tends to be one. Naming it gets further than a question about delegation in the abstract. The reason they held on, often a belief that nobody else would do it properly, is the part to stay with.
Did you start alone or with a partner, and would you choose the same again?
Why ask it
Solo founders talk about loneliness and partners talk about disagreement, and both are being honest. If there was a partner, ask how they split the work and whether any of it was written down. If the partnership ended, one question about it is enough.
Who were your mentors, and how did you find them?
Why ask it
It is seldom a formal arrangement. You are more likely to hear about a former boss, a customer or an older owner in the same trade who took a call once a month. The finding is the practical half, so ask what they first asked that person for.
How did you build a network when you did not know anyone?
Why ask it
Worth asking if you are starting without contacts, since people who now know everyone can forget they once knew nobody. The routes are usually plain ones: a trade association, one generous customer, turning up to the same event for a year. If they began with a full address book, that is an advantage to note and adjust for.
Who tells you when you are wrong, and how do you take it?
Why ask it
A name is what you want: a cofounder, a board member, a long-serving employee, a spouse. Then ask for the last time that person changed their mind about something. If the answer stays general, about welcoming challenge, leave it there and draw your own conclusion.
Running it
What does a typical day look like for you now, and is it what you expected?
Why ask it
The work tends to shift from making the thing to hiring, selling and managing the people who make it. Hearing what a day holds at their stage is a realistic preview, and it can be the part people find they do not want. A good follow-up is which task they would hand to someone else tomorrow.
What time does your day start, and what is the first hour for?
Why ask it
Everyone wants the morning routine, and the alarm time is the least useful part of it. What matters is what they protect before the day gets taken over: thinking time, exercise, the school run, an hour without email. Borrow the principle and ignore the clock.
What habit kept things moving through the slow months?
Why ask it
A lot of running a business is unremarkable months, and the habits that carry those seldom make it into the story. Answers tend to be small: a weekly number reviewed, ten calls a day, a Friday walk, one customer conversation a week. That is what the word discipline looks like in practice.
What keeps you motivated now that the business is established?
Why ask it
The reason someone starts and the reason they carry on are often different. Early fuel such as money or proving someone wrong may have run out, so listen for what replaced it: the team, the craft, a rival, a customer they like serving. If motivation simply comes and goes, ask what they do on the days it is missing.
After the first few customers, what has worked best for finding more?
Why ask it
Early customers tend to come through people the founder already knows, and the next hundred need something repeatable. Ask what they tried that failed before the thing that worked, and how long they gave each attempt. A channel that suited their trade five years ago may be crowded now, so check whether they would still begin there.
What do customers get from you that they could not get from a competitor?
Why ask it
The practised answer is quality or service. A better one names something narrow: a faster turnaround, a niche nobody else bothers with, a person who picks up the phone. How they found out is worth hearing too, since that kind of thing is usually learned from a customer and not in a strategy meeting.
What opportunity did you turn down, and how did you decide?
Why ask it
A business is shaped by its refusals as much as by its launches: the big customer who would have bent the product out of shape, the investor, the partnership. Ask for one they turned down and one they regret accepting. The reasoning is more use to you than any framework.
What do people misunderstand about your business?
Why ask it
You often get the unglamorous economics here: the margins, the seasonality, the fact that most of the revenue comes from a product nobody talks about. It is also a question owners tend to enjoy, which helps if the conversation has gone stiff.
What books, podcasts or people do you learn from these days?
Why ask it
You may get a title or two, and it is worth writing them down. Then turn to the people, since owners at this stage often learn more from peers a few years ahead, from their own customers and from the occasional paid adviser. End on the last thing they learned that changed how they run a normal week.
How do you stop the business taking over the rest of your life?
Why ask it
Ask for the rule, not the philosophy: no phone at dinner, one full day off, holidays booked a year ahead. Plenty will admit they have no rule and wish they did. Either reply is more honest than a sentence about balance.
What has the business cost you personally?
Why ask it
Not one for a panel, or for a room with their staff in it. Late in a one-to-one it is the counterweight to every account of success, and the answer can be heavy: a marriage that did not last, a decade of missed school plays, their health. Say it once and let them decide how far to go.
What is not going well right now?
Why ask it
Unexpected in a conversation framed around success, and it changes the register. You get a live problem and not a settled story, and this is often where the exchange becomes mutual. Skip it on a panel, where nobody can afford to answer it straight.
What are your plans for the business over the next five years?
Why ask it
Some will describe growth, some a sale, some a smaller company that needs them less. None of those is a wrong answer, and each changes how to read the rest of what they told you. A founder preparing to sell gives different advice from one who means to pass the business on to family.
What would have to happen for you to walk away from this?
Why ask it
For some owners the business is who they are, and for others it is an asset with a price and conditions. This shows which. The conditions they name, an offer, their health, a child who does or does not want to take over, tend to be what is on their mind this year.
Lessons and advice
How do you define success now, and has that changed?
Why ask it
The definition they started with was probably a number: a turnover figure, a headcount, the day they could quit the job. Ask what replaced it once the number was reached, and whether reaching it felt the way they expected. That second answer is a fair preview of your own targets moving.
How much of your success would you put down to luck or timing?
Why ask it
Asked plainly, this tends to get a thoughtful answer, because people who have done well can usually point to the coincidence that helped: good timing, one introduction, a competitor's mistake. Follow it with what they did to be in a position to use it. Someone who cannot name any luck at all is worth hearing a little more sceptically.
What are you most proud of in the business?
Why ask it
It is often not the thing in their biography. People name an employee who went on to start a firm of their own, a customer kept for twenty years, a bad year survived without laying anyone off. What they pick tells you what the business is for, in their own mind.
What do you wish someone had told you in your first year?
Why ask it
The practised answer is a tidy lesson. Push for the thing they would not have believed even if told: how long everything takes, how much of managing is repetition, how little customers cared about the feature they were proudest of. Then ask who could have told them, and whether they would have listened.
If you were starting in this field today, what would you do differently?
Why ask it
This moves them from reminiscing to the market as it is now, which they are well placed to read. Sometimes the answer is that the route they took has closed: the cheap advertising, the empty niche, the lender who said yes. That is more use to you than a formula that no longer works.
What is the best piece of business advice you were ever given?
Why ask it
Pin down how old the company was when they heard it. A line that saved them in year two, such as raise your prices or stop taking custom work, may be wrong for someone in month two. If they cannot say where it came from, it may be a slogan and not something they acted on.
Which piece of common business advice did you ignore, and were you right to?
Why ask it
Experienced people get interesting when they disagree with the usual wisdom, and this gives them permission. The second half keeps it honest, since sometimes the ignored advice was correct and cost them a year. Either way it is a reminder to hold their own advice to the same test.
Which skill has mattered most, and did you have it when you started?
Why ask it
Expect selling, managing people or reading a set of accounts at least as often as anything technical. The second half is the encouraging part if they say they learned it late and badly. Ask how they would pick it up faster now.
What advice would you give someone who is just starting out?
Why ask it
They have answered this more often than any other question, so the first reply will be the practised one. Take it, then ask whether they followed it themselves when they began. The gap between the advice and what they actually did is worth more than the advice.
If you were in my position, what would you do in the next month?
Why ask it
It only works once they know your position, so give it in two sentences first. A month is short enough to force a concrete step: ten calls, a price test, one conversation you have been avoiding. Write the answer down in their words, and if you act on it you have a reason to get back in touch.
What should people in my position ask you that they never do?
Why ask it
This hands them the last few minutes, and people who field the same handful of questions at every event tend to have an answer ready. What comes back is often about the dull middle years of building something. Give them a moment to think before you fill the silence.
Who else should I talk to, and may I say you sent me?
Why ask it
The most practical way to end a meeting of this kind. One name offered freely is worth more than an introduction you had to push for, and the second half means you leave knowing whether you can use theirs.
Making a short conversation count
Practical guidance for the conversation itself
Before you meet
- Read or listen to one interview they have already given, then cross off every question it answered. Asking what they have said publicly ten times is how a conversation becomes a recital.
- Decide what you want from the conversation: one decision tested, one introduction, one specific piece of advice. Vague admiration produces vague answers.
- Pick five questions and rank them. You may only get through three, so put first the one you most want answered.
- Take one or two questions from each group instead of five from one. Twenty minutes spent only on money or only on mistakes starts to feel like an audit, and you leave without the rest of the picture.
- Write down your own situation in two sentences so you can give context quickly when asked. Advice improves sharply once they know what you are actually doing.
During the conversation
Use the familiar question as a door
The questions everybody asks, about the idea, the biggest challenge and the advice for beginners, make good openers because they are easy to answer. The first reply will be one they have given before. What you came for is in the second question, the one that asks for the date, the number or the name.
Ask for the instance, not the principle
"How do you think about hiring?" produces a philosophy. "Tell me about the last person you hired who did not work out" produces an account with decisions in it. Convert every general question into a specific one before you ask it.
Ask for numbers and dates
How long, how much, how many. People who run a business tend to know these, and they anchor a story that would otherwise float. A refusal is fine and tells you where the boundary is.
Follow the flinch
When someone hesitates or moves past something quickly, there is often more there. One gentle follow-up is usually welcome and two is an interrogation. If the subject is their family or their health, let it go.
Say the uncomfortable question plainly
Questions about luck, advantage and personal cost work when asked simply and without apology. Long preambles signal that you expect the question to offend, which makes it offensive.
If it is a panel or an assignment
On a panel you get one question, so choose one the room could not answer from the speaker's website, and keep it to a single sentence. For a class or college interview, say at the start how long it will take and what the write-up is for, and ask before you record.
Common pitfalls
Asking for the secret
Questions about the key to success invite the answer they give on stage. There is rarely one cause, and asking as though there were gets you the least specific version of their thinking.
Pitching instead of asking
If you spend the time describing your own idea, you get politeness rather than information. Ask for their experience; if they want to hear your plan, they will ask.
Treating survivorship as method
One person's route is a single data point, shaped by timing you cannot reproduce. Ask what they think was replicable and what was circumstantial, and take their answer to that seriously.
Asking for a favour before you have earned it
A request for funding, a job or a list of introductions in a first conversation tends to cool it. If you want something concrete, ask for the smallest version: one name, or one opinion on one decision.
Afterwards
Write it down within the hour
Record the numbers, the dates and the exact phrasing of anything that struck you. Paraphrased advice loses the specificity that made it useful, and that is the part you will want in six months.
Send one short note
Two or three sentences naming the one thing you are going to do differently. It is more memorable than gratitude in general terms and it makes a second conversation possible.
Report back once, later
If you act on something they said, tell them what happened a few months on. Few people do, and it gives them a reason to take your next call.