Questions to Ask an Entrepreneur Interview
For a recorded or written interview with a founder, whether for a podcast, a school assignment, a company profile or a student newspaper: twenty questions that produce stories and specifics rather than the pitch they have given ten times already.
The questions
Open any question for the note
Describe what the company does in a sentence someone outside your industry would follow.
Why ask it
It gives you a usable opening quote and shows how clearly they think. Founders who cannot do it without jargon usually cannot do it with customers either, which is worth noting for later questions.
What were you doing the year before you started?
Why ask it
The year before is more revealing than the founding moment: a job they hated, a redundancy, a problem they kept hitting, a client who asked for something nobody sold. It also dates the story properly for your audience.
Who bought the first one, and what did they pay?
Why ask it
A named first customer and a real price turn an origin story into something concrete. If they cannot remember, that is interesting too, and usually means the first sale was to someone they knew.
Where does the money actually come from now?
Why ask it
Interviews often skate over the business model. Ask which product or customer type brings in most of the revenue, because the answer is frequently not the thing the company is known for.
What was the hardest week, and what happened during it?
Why ask it
A week is short enough to force detail and long enough to contain a story. You are looking for the specific events, a missed payroll, a lost client, a co-founder leaving, not a reflection on resilience.
What did you believe about your market that turned out to be wrong?
Why ask it
This gets an admission of error without asking about failure directly, which most founders have a rehearsed answer for. The correction usually came from a customer, so follow up on who told them.
What decision is still argued about internally?
Why ask it
Live disagreements are more interesting than settled ones and are the part rarely aired in public. If they say nothing is argued about, ask who disagrees with them most and what about.
Which competitor do you respect, and what do they do better than you?
Why ask it
The answer separates confidence from bluster, and the specificity of the praise is the tell. A dismissive answer about having no real competitors is worth pressing rather than printing.
What part of running this are you worst at?
Why ask it
Asked plainly, it usually gets an honest answer, and it produces the most human quote in the piece. Follow up with who covers that gap now, which tells you how the company is actually organised.
Who told you no, and what did you do next?
Why ask it
Rejections by investors, retailers, distributors and first hires are all part of the record, and the next move is the substance. It also gives you names and dates you can check afterwards.
How do you decide what not to do?
Why ask it
Strategy is visible in refusals more than in plans. Ask for an example of something attractive they turned down, because the general answer will be a slogan.
What do you know now that would have saved you a year?
Why ask it
The framing gets a usable, quotable answer without asking for advice, which produces platitudes. Ask what specifically cost the year, since that is the part readers can act on.
How many people work here, and what changed about your job when the team got past ten?
Why ask it
Headcount is a fact your audience needs, and the second half surfaces the shift from doing the work to managing it. Founders are often candid that they miss the earlier job.
What do you look at every week?
Why ask it
The weekly numbers show what the company is really run on: cash, bookings, churn, utilisation, waiting lists. If nothing is looked at weekly, ask what tells them something is wrong.
What would have to happen for this business to be in trouble in two years?
Why ask it
Better than asking about risks, because it asks them to describe a chain of events. Careful answers name a supplier, a platform, a regulation or one large customer, which is the honest shape of most risk.
What is the least glamorous part of your week?
Why ask it
It punctures the founder profile genre and usually produces the detail readers remember: invoices, a warehouse, complaints, a long drive. Ask for what they did yesterday if the answer is abstract.
What advice do you hear repeated in your industry that you think is wrong?
Why ask it
It invites a real opinion and gives your piece something more than agreement. Ask what they do instead, so the disagreement lands somewhere concrete.
What did you give up to do this?
Why ask it
Kept short and then followed by silence, this gets past the cost being described as a worthwhile trade. Be ready to hand control back: they may want part of it off the record, and honouring that gets you the rest.
What do you want to be doing in five years, and is it this?
Why ask it
The second clause is the question. Founders who have been asked about their five year plan a hundred times have not usually been asked whether they still want the job.
What have I not asked that I should have?
Why ask it
It hands them the last word and often produces the story they came in wanting to tell. Leave two minutes for it rather than asking it while packing up.
Running the Interview
Practical guidance for the conversation itself
Before you record
- Listen to or read their last two or three interviews. Repeating a question they have answered word for word wastes your best minutes and tells them you did not prepare.
- Agree the shape in advance: how long, what the piece is for, where it will run, and anything genuinely off limits. Agreeing one topic to avoid is normal and buys you frankness elsewhere.
- Say clearly that you are recording, and get that on the recording. If you may quote numbers about funding or revenue, ask then whether those are on the record.
- Send two or three questions in advance rather than all twenty. Enough to prepare, not enough to script.
- Bring a spare recorder or record on a second device. Losing the audio of a good interview cannot be repaired.
- Find out who else you could ask about the same events, an early employee, a first customer, in case you need a second source.
While you are talking
One question at a time
Stacked questions get answered in the easiest part and the rest is dropped. Ask the short version and wait.
Ask for the scene, not the lesson
Where were you, who was in the room, what did you say. Founders default to the moral of the story because that is what they are used to being asked for.
Let silence do the work
Three seconds of nothing after an answer is the most productive tool in an interview. Most interviewers fill it and lose the second half of the answer.
When they retreat to talking points, ask for the date
What month was that, who told you, what did the email say. Specifics break a rehearsed narrative more effectively than a challenge does.
Ask the awkward question late and plainly
Once there is some trust in the room, ask it in one sentence without softening it. Long preambles signal that you expect to be refused.
After the interview
- Check the checkable claims: founding dates, funding rounds, award wins, being the first to do something, employee counts. Firsts and superlatives are where founder accounts most often drift.
- Note where a story is theirs alone. If nobody else can confirm it, present it as their account rather than as fact.
- Send corrections of fact and quotes for accuracy if that is your standard, but do not hand over editorial control over the framing.
- Keep the recording and your notes after publication. If a claim is disputed later, the tape is what settles it.
- Send the link when it runs, and say what you cut and why if a lot came out. It costs nothing and it is why people say yes the next time.
If this is a school or college assignment
- Say in your first email that it is coursework, how long you need, and when you need it by. Most founders say yes to students and appreciate the honesty.
- Twenty minutes and six questions you actually care about beats an hour of a printed list.
- Ask about the boring middle of the business rather than the founding story. It is where the marks are and where the interesting material sits.
- Quote them accurately and send them the finished piece. It takes two minutes and it makes the next student's request easier.