50 Questions to Ask an Entrepreneur
A single ordered interview rather than a list to dip into. The fifty questions run in the order you would actually ask them, from easy opening ground through the first year, money, customers, hiring and the personal cost, to the closing questions worth saving for the end, which is roughly an hour of recorded conversation. If you want a bank to select from by theme, use the 100 questions to ask an entrepreneur reference, and if you have twenty minutes over coffee, the standard set is a better fit.
The questions
Open any question for the note
Tell me what the business does, as if I were a customer rather than an investor.
Why ask it
Opening on the customer version keeps the first answer in plain words and tells you which audience the founder is most used to talking to. If the reply still comes out as a funding pitch, that is worth noticing before you go further.
How long has it been running, and what stages would you divide it into?
Why ask it
This gives you the shape of the story early, so you can time the rest of the session. The names a founder gives each stage also show which period they consider the real turning point.
What were you doing in the year before you started?
Why ask it
The year before explains the resources, contacts and frustrations they began with. It is also an easy question to answer, which is what you want while the recorder is still settling.
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.
What did you tell people you were doing at the time?
Why ask it
How they described themselves before it worked shows how confident they actually were. The gap between that and the current description is often the most human part of the interview.
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 the first person to pay you, and what did they buy?
Why ask it
Naming one customer forces specifics rather than a description of a market. Ask what the approach sounded like, since that is the part another person could repeat.
How long was it between starting and the first money arriving?
Why ask it
The length of that gap sets the difficulty of everything else in the first year. It also lets you ask what they lived on while it lasted.
How did you cover your own living costs that year?
Why ask it
Savings, a partner's salary, contract work and family support all lead to different stories about risk. It is a fair question in a long interview and it grounds the rest of the money section.
What did you assume about your customers that turned out to be wrong?
Why ask it
Every founder has one. The correction usually explains a pivot better than the pivot story does.
How do you find out what customers want, other than asking them?
Why ask it
Watching cancellations, support tickets and the workarounds people build tells you more than a survey. The answer shows how close the founder still is to users.
Which complaint changed the product?
Why ask it
One specific complaint tends to be behind most of the good decisions. It also shows how the company handles being told it is wrong.
What do customers use it for that you did not design it for?
Why ask it
Unplanned uses are where the next version usually comes from. If the founder cannot name one, they may not be watching closely enough.
What is the most common reason someone says no?
Why ask it
Sales objections describe the market more honestly than a market size figure does. Ask whether the reason has changed over time.
Who is this not for, and do you tell them so?
Why ask it
A founder who can turn away a poor fit usually understands the product. A founder who says it suits everyone is normally still guessing.
How did you set the first price, and what happened when you raised it?
Why ask it
First prices are almost always a guess, and the first increase is where founders learn what the product is worth. The story of that increase is the useful half.
What does a sale actually leave you once everything is counted?
Why ask it
Delivery, support, payment fees and refunds sit between revenue and what is left. The answer separates founders who track this from founders who quote a headline number.
How many months could you run with no new sales?
Why ask it
This is the single number that decides how a business behaves under pressure. It tends to explain hiring and pricing decisions you asked about earlier.
What was the worst thing you spent money on?
Why ask it
Spending regrets are easier to admit than strategic ones, and they are specific. Ask what they would spend it on now instead.
Did you take outside money, and what changed the week after?
Why ask it
The week after a raise is when the job quietly changes: new reporting, new expectations, faster hiring. Founders who chose not to raise usually have an equally clear answer about what that cost.
When did you start paying yourself, and how did you pick the number?
Why ask it
The date and the method say a lot about how the business was run early on. Halfway through a long session is the right time to ask, once some trust exists.
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 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 did you build that nobody wanted?
Why ask it
Wasted work is a normal part of the story and a good test of candour. The interesting part is how long it took them to accept it.
Which decision did you delay, and what did the delay cost?
Why ask it
Delay costs are usually larger than the wrong decision would have been. This one produces advice other people can act on.
Who did you hire first, and what did you misjudge about the process?
Why ask it
First hires are made under pressure and with no process. The misjudgement is where the useful detail sits.
What do you screen for now that you did not know to look for?
Why ask it
The answer shows what actually went wrong with earlier hires without naming anyone. It also tells you what the company is like to work in.
What is the hardest conversation you have had with someone who worked for you?
Why ask it
Redundancies, demotions and a friend who did not work out are all common. How they describe it shows whether they took responsibility or outsourced it.
What happens here when someone is good at the work and difficult to be around?
Why ask it
Every company faces this and the answer reveals the real standard rather than the stated one. Ask for a case rather than a policy.
What do you want people to say about this place after they leave?
Why ask it
Asking about leavers rather than staff gets a more honest description of the culture. It also sets up the question of whether that is currently true.
Who has been hardest to replace?
Why ask it
The person hardest to replace tells you where the knowledge sits. It often points at a risk the founder has not addressed.
How do you decide what to work on in a given week?
Why ask it
Method matters more than the list. Look for whether anything gets dropped, or whether everything stays on the list forever.
How do you make a call when the information runs out?
Why ask it
Founders decide with gaps constantly. The rule they use, whatever it is, is more portable than any single decision.
How do you tell a slow start from a bad idea?
Why ask it
This is the question most founders are still working on. Expect an honest answer about a time they got it wrong in both directions.
What have you said no to that you still think about?
Why ask it
The refused opportunity is usually remembered in detail. It shows what the founder values when the two options were close.
What number do you look at first in the morning?
Why ask it
One number, chosen daily, describes what the founder believes the business runs on. Ask whether it was a different number two years ago.
What is the bottleneck right now?
Why ask it
This drags the interview into the present after a long stretch of history. It also gives you something concrete to follow up on later.
Who do you actually watch in your market, and what do they do better?
Why ask it
Founders who name a specific competitor and a specific strength are paying attention. Vague dismissal usually means they are not.
What do you understand about your buyers that your competitors seem not to?
Why ask it
This invites a claim they then have to support. The supporting detail is where the real market knowledge shows.
What could end this business?
Why ask it
Asked directly, most founders answer honestly: a platform change, one large customer, a key person, a rate. The list they give is their actual risk register.
What does a bad week look like now, and how often do they come round?
Why ask it
Comparing a bad week now with a bad week early on measures how far the business has come. It also opens the personal section gently.
What have you given up that you did not expect to give up?
Why ask it
The unexpected losses are often small and specific: a sport, a friendship, a habit. They tell the cost story better than long hours do.
Who can you speak to honestly about the business?
Why ask it
Founders who cannot name anyone are usually carrying more than they say. The answer often explains their decision-making style too.
When did you last take a full week off?
Why ask it
The date, and what happened while they were away, tests how much of the company still runs through one person. Ask what broke, if anything.
How do you tell being tired from being finished with it?
Why ask it
This gives the founder room to be honest late in a session without asking them to confess anything. Many have thought about it more than they admit.
What do you know now that would have made the first two years shorter?
Why ask it
A closing question that produces the most quotable answer of the session. It also summarises everything earlier in their own words.
What would you do in a different order if you started again tomorrow?
Why ask it
Order is usually where founders would change things rather than the decisions themselves. It is more useful than a general list of regrets.
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.
How will you know when it is time to hand this over?
Why ask it
Succession is rarely discussed and the answer shows whether they think of the business as separate from themselves. Expect a pause.
What have I not asked that you expected me to?
Why ask it
The standard closing question, and it works. Whatever they raise is the thing they most wanted on the record.
Interviewing a founder well
Practical guidance for the conversation itself
Do the homework that changes your questions
Read what they have already said
Founders repeat their origin story on podcasts, in funding announcements, and on their own about page. Read two or three of those first so you can skip the version they have rehearsed and ask about the part everyone leaves out.
Know what stage they are at
Pre-revenue, first ten customers, and forty employees are three different jobs. Hiring and delegation questions land badly on a solo founder; validation questions feel remedial to someone eight years in. Check headcount and any funding news before you write your list.
Decide what you want out of it
An interview for an audience needs stories and specifics. A mentoring conversation needs your own situation on the table so their advice can be aimed. Due diligence needs numbers and dates. Trying to do all three in one sitting produces a shallow version of each.
Getting past the pitch
Founders are practiced at answering in narrative, and the narrative smooths over the interesting parts. A few habits pull the conversation back to specifics:
- Ask for a date or a moment. "When did that stop working?" gets a real answer where "how do you handle growth?" gets a philosophy.
- Ask about the decision, not the outcome. Successful outcomes get explained backward as if they were planned.
- Follow a general answer with "what did that look like last month?" once. Doing it every time feels like cross-examination.
- Let a pause run. Founders often add the honest qualifier three seconds after they finish the polished sentence.
- Ask what they would need to see to change their mind. It surfaces the assumption the whole plan rests on.
Where these conversations go wrong
Asking for the secret
Questions shaped like "what is the key to success" invite the founder to generalize from one company, which is the least reliable thing they can tell you. Ask what happened instead, and draw your own conclusions.
Treating survival as strategy
A founder who is still in business will explain their choices as deliberate. Much of it was timing, a lucky first customer, or a competitor who stumbled. It is fair to ask directly which parts they think were luck; most will answer honestly.
Asking numbers they cannot share
Revenue, burn, and valuation are often under investor or customer confidentiality. Ask for direction and scale, whether they are growing, whether it is doubling or inching, rather than exact figures, and you will get an answer instead of a deflection.
Skipping the boring operations
Pricing changes, collections, hiring a bookkeeper, and switching suppliers are where most of the actual learning sits. Founders rarely volunteer this material because no one asks for it, which is exactly why it is worth asking for.
Adjusting for the setting
Recorded interview
Open with something concrete and easy, like the Tuesday question, so the first minute is not a monologue. Save the near-shutdown question for the second half, once they have decided you are asking in good faith.
Mentoring or coffee
Bring one real problem of your own. Founders give much better answers to "here is my situation, what would you do" than to open-ended questions about their journey, and it respects the fact that they came to help.
School or research project
Send two or three questions ahead of time and say how long you need. Ask permission before recording. Follow up afterward with what you ended up writing, which is the main reason founders agree to a second interview.
Considering joining them
The delegation, firing, and succession questions matter more than the vision. They tell you what working there is actually like, and whether the role you are being offered has real authority attached to it.