Business Questions to Ask an Entrepreneur
Twenty-one questions for a conversation with a founder, whether it is a coffee, a podcast, a class visit or a call before you invest. They ask for specifics: the first six months, where the money came from, how the first customers were found, what hiring taught them, and what they would do differently now.
The questions
Open any question for the note
What were you doing before this, and what pushed you out of it?
Why ask it
Openers about origin stories usually get a polished version, so listen for the push rather than the pull. Founders who left because of a specific frustration tend to give concrete answers, while a story about always being entrepreneurial is a sign you are getting the keynote.
What did the first six months actually look like, day to day?
Why ask it
This gets past the strategy and into the work: cold emails, a spare room, a job kept on the side. The detail is what an aspiring founder can use, and vagueness here often means someone else did the early grind.
How did you fund the beginning, and what did that cost you?
Why ask it
Ask for the mechanism, savings, a loan, a friend, a first customer paying upfront, and then for the cost, in equity, in hours, or in personal risk. Answers that skip the cost tend to make starting up sound cheaper than it was for them.
Who were your first ten customers, and how did you find them?
Why ask it
The best single question on this list, because the answer is checkable and impossible to fake convincingly. Most early customers come from someone the founder already knew, and hearing that honestly is more useful than any theory about go-to-market.
What did you believe about the market that turned out to be wrong?
Why ask it
This asks for a specific error, which is harder to answer than a general lesson and therefore more revealing. A founder who cannot name one either has not been running long or is not listening to their customers.
Which mistake in the first year cost you the most?
Why ask it
Attaching a cost to the mistake stops the answer becoming a humblebrag about moving too fast. Ask what the cost was in money or months, and whether anything in the business changed as a result, since that is the part people skip.
Before there was revenue, what told you it was working?
Why ask it
Founders who can name a real early signal, a customer chasing them for the product, someone paying before it was finished, understand their own business. Answers about belief and passion mean the evidence came later, or has not arrived.
What are you personally spending your days on now?
Why ask it
Compare it to what they say the priority is, because the calendar is the honest version. A founder still doing sales calls three years in is telling you something about their team, and a founder doing nothing but meetings is telling you something else.
What was the first role you hired for, and did it work out?
Why ask it
First hires are usually made in a panic and often replaced, and hearing which one they got wrong teaches more than an answer about culture. Ask what they would look for now, since the criteria change more than the job description does.
What have you learned about letting someone go?
Why ask it
The management question most people leave out, and the one that shows whether they lead or just recruit. Listen for whether they talk about acting sooner, and whether they take any responsibility for the hire in the first place.
How do you decide what not to do?
Why ask it
Most founders can list opportunities. Far fewer can describe a request they turned down and why, so ask for a specific customer or a specific market they walked away from. A no with a reason behind it is the mark of someone with an actual strategy.
Have you changed direction, and what convinced you?
Why ask it
The convincing evidence is the substance here, not the pivot. Watch for whether the change came from data, from a customer, or from a bad month and a nervous board, since those produce different quality of decisions.
Where does the money actually come from in your business?
Why ask it
Ask which product, which customer segment, and which part carries the margin. Founders often discover their revenue is more concentrated than their pitch suggests, and anyone who cannot break it down is running on gross numbers alone.
Which number do you look at first in the morning?
Why ask it
This exposes what they genuinely manage by, as opposed to the metrics on the slide. A founder who checks cash, or one specific weekly figure, is usually closer to the business than one who names a dashboard.
What has growth broken that used to work fine?
Why ask it
Every stage kills a process that suited the last one, hiring by instinct, doing support personally, one shared inbox. Naming what broke shows they have been through a real transition rather than describing scale in the abstract.
How do you handle the conversation with investors when a quarter goes badly?
Why ask it
You learn about candor and about their board in one answer. Founders who describe telling people early tend to have calmer investors, while a story about managing the message says a great deal about the relationship.
What has this cost you outside work?
Why ask it
Ask it plainly and let them decide how much to say. The answers to be skeptical of are the ones claiming no cost at all, and the more honest ones, about health, friends, or a partner who carried more than their share, are what most audiences never hear.
Which decision still bothers you?
Why ask it
Late enough in a conversation, this gets the unresolved thing rather than the tidy lesson. Regret without a moral attached is a sign you are getting a real answer, and it is usually about a person rather than a strategy.
What is your company genuinely bad at?
Why ask it
A useful test of self-awareness, and the answer is often more informative than any list of strengths. Watch for the humblebrag disguised as a weakness, caring too much, moving too fast, which tells you the honest version is not on offer today.
If you started again tomorrow, what would you do differently?
Why ask it
Better than asking what advice they have, because it forces them to be concrete about their own case. If the answer is nothing, ask about the first year again, since almost nobody who has done it twice would repeat the first attempt exactly.
What advice do you give that people usually ignore?
Why ask it
A sharper closer than asking for advice generally, since it surfaces the unglamorous counsel about charging more, firing faster, or talking to customers before building. The fact that people ignore it is often why it is worth hearing.
Interviewing a founder well
Practical guidance for the conversation itself
Before the conversation
Read what they have already said
Founders repeat their story constantly. Spend twenty minutes on their site, a podcast appearance, or their last funding announcement, then skip everything you already know. Asking what the company does wastes the best part of your time.
Decide what you want out of it
A conversation aimed at starting your own thing should dwell on the first year. One aimed at working for them should focus on hiring and decisions. One aimed at investing should focus on customers, revenue concentration and cash. Mixing all three gets you a shallow version of each.
Bring three questions, not twenty
Half an hour holds three real questions with follow-ups. Choose the ones only this person can answer, and let the rest go.
During the conversation
- 1Ask for a specific instance whenever you get a general principle. The phrase to use is: when did that last happen?
- 2Follow every claim of growth with a question about the denominator, from what to what, and over what period.
- 3When an answer sounds rehearsed, ask about the same event from a different angle: what it cost, who disagreed, what nearly happened instead.
- 4Let a pause sit after a hard question. Founders often correct their own polished answer if nobody fills the gap.
- 5Take the numbers down as they are said, and read them back at the end so you are not reconstructing them later.
What goes wrong
Treating one founder's route as the rule
You are hearing from someone whose company survived. The same choices were made by others who did not, so ask what they think was luck, and take the pattern advice lightly.
Asking for the secret
Questions about the key to success get platitudes, because there is no single answer to give. Specific questions about specific months get specific answers.
Pitching instead of asking
If you spend the meeting describing your own idea, you learn nothing and use up the goodwill. Ask your questions, then offer your idea only if there is time left and they invite it.
Ignoring what is confidential
Revenue, salaries, cap tables and customer names may not be theirs to share, especially with investors involved. Ask, accept a no gracefully, and ask for a range or a shape instead.
Adjusting for the setting
Coffee or a favor
You have twenty minutes and no claim on more. Ask two questions, take notes, send a short thank you saying what you did with the advice. That last part is what earns a second conversation.
Recorded interview or panel
Your audience needs the context, so let the founder set the scene briefly, then go straight to the specific questions. Save the personal cost question for late, once they trust the room.
Students in the room
Ask about the first six months and the first ten customers, since that is the part of the story that transfers. Skip the strategy questions, which produce answers nobody can act on yet.
Diligence before investing
Stay with revenue concentration, customer acquisition, churn and cash runway, and expect to verify each answer elsewhere. Ask who else you may speak to, and treat reluctance as information.