Questions to Ask an Entrepreneur During an Interview
Questions to ask an entrepreneur during an interview, whether it is for a class assignment, a podcast, a company profile or a student newspaper. The 60 questions run in the order an interview usually does: how it started, how the business works, the hard times, the people and the routine, what they have learned and what comes next. The standard ones are all here (why they started, the biggest challenge, the advice they would give), and each has a note on how to get a story and specifics in place of the pitch they have given ten times already.
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The questions
Each question, and why to ask it
Starting out
What does the business do, in a sentence someone outside your industry would follow?
Why ask it
Start here even if you already know: it gives you a plain sentence to open the piece with, in their words and not the website's. If it comes out as jargon, ask what a customer would say they bought.
Why did you decide to start your own business instead of working for someone else?
Why ask it
Every audience expects this one answered, so ask it early. Wanting to be their own boss is the reply you will hear first. The event that made them finally act on it is your story.
Where did the idea for the business come from?
Why ask it
Ideas rarely arrive in the single flash the retelling suggests. Listen for the first version, a different product or a different customer, and ask what made them change it, which is often a better scene than the idea itself.
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 layoff, a problem they kept hitting, a client who asked for something nobody sold. It also dates the story properly for your audience.
How much money did it take to get started, and where did it come from?
Why ask it
Savings, a family loan, a bank, an investor or a credit card each make a different story about risk. Agree before you publish whether the figure is on the record. Should they prefer not to name one, ask what the money had to cover.
Did you write a business plan before you started, and how much of it held up?
Why ask it
A standard for class assignments, and the replies vary: a bank insisted on one, they did a page of sums, or there was nothing on paper at all. Whichever it is, ask for one thing in the plan, or in their head, that the first year proved wrong.
Do you remember your first sale: who bought, and what did they pay?
Why ask it
A named first customer and a real price turn an origin story into something concrete. If the buyer was a friend or a relative, ask about the first stranger who paid, which is often the sale they count as the real one.
How did people find out about you when the business was brand new?
Why ask it
Early marketing is nearly always unglamorous: flyers, a market stall, a hundred messages to strangers, a favor from a friend with a following. Ask which of those efforts they would not bother with again.
Who backed the idea early, and who tried to talk you out of it?
Why ask it
Two sets of names come out of this, and both are people you could contact for a second voice. The doubter is often a parent or a former boss, and what the founder says about that person now tends to be quotable.
Was anyone in your family self-employed when you were growing up?
Why ask it
A parent with a shop, a farm or a trade can make self-employment seem ordinary, and a family of employees can make it look like a break with what was expected. Ask which it was for them and what the family says about the business now.
How did you choose the name?
Why ask it
A small question that loosens people up. There is nearly always a story behind it: a rejected shortlist, a web address that was taken, a name they would now change. Keep it in reserve for a moment when the interview has gone stiff.
Was there a day when you knew it was going to work?
Why ask it
Some can name it to the date: an order from a stranger, the first month the account stayed in the black, an employee's first payday. A founder who says that day has not come yet is giving you a more honest piece, so do not hurry past it.
The business
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.
How long did it take for the business to turn a profit?
Why ask it
Get it in months or years, then check what they mean by profit: for some owners the milestone that counted was the first month they could pay themselves. If it is not there yet, ask what has to change, and whether that answer is on the record.
Who is your typical customer, and is that who you expected it to be?
Why ask it
Ask them to describe one real person or company, not a segment. The gap between the customer they planned for and the one who turned up often explains the changes the business has made since.
How do new customers find you these days?
Why ask it
Word of mouth is the reply you will hear first, and it is too vague to print. Ask where the last three customers came from, and you get a referral, a search result or a sign on a van, plus a sense of whether they keep track.
What do customers get from you that they could not get from someone else?
Why ask it
This is the what-sets-you-apart question, pointed at the customer so that the reply has to be about something a buyer would notice. If you hear quality and service, ask when a customer last told them why they chose them.
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 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.
How is the business different now from its first year?
Why ask it
Products get dropped, prices go up, the customer changes, the founder stops doing the work and starts managing it. Ask which change they resisted longest, since a reluctant change makes a better story than a planned one.
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.
Which figures do you check every week?
Why ask it
The weekly numbers show what the business is really run on: cash in the bank, bookings, cancellations, the length of the waiting list. If nothing gets checked weekly, ask what tells them something is wrong.
What will you not compromise on, even when it costs you a sale?
Why ask it
Values only show once they have cost something, so ask for the order they turned away or the corner they refused to cut. If no example comes, treat the principle as an aim and do not print it as a fact about the company.
What is the strangest thing a customer has ever asked for?
Why ask it
A light one for the middle of a long interview: it usually brings a laugh and a story, and it shows sideways where the business draws its line and how they talk about customers once they relax.
Hard times
What has been the biggest challenge of running the business so far?
Why ask it
Broad on purpose: what they pick tells you whether the hard part has been money, people or their own stamina. Whatever they name, ask for one occasion when it came to a head, because the general version will not carry a paragraph.
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 is the biggest mistake you have made in the business?
Why ask it
Expect it to be about a person or about money, since those are the two that hurt. The follow-up worth having is how long it took them to see it as a mistake, because that gap is where readers recognize themselves.
What have you tried that failed completely?
Why ask it
Different from a mistake: this is a product, a second location or a partnership that simply did not work. Ask what happened to the stock, the lease or the people afterwards, since the clean-up is usually missing from the public version.
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.
Have you ever come close to giving up?
Why ask it
Ask it as a yes or no and let them choose how much to add. If it is a yes, the detail to get is what was different on the morning they decided to carry on: a payment that arrived, a conversation, plain stubbornness.
What do you do on the days you doubt the whole thing?
Why ask it
Fear and doubt come up in most founder interviews, and asking what they do keeps the reply practical. You might hear about a walk, a call to one particular person, or opening the order book to look at real numbers.
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 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 organized.
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 criticism of the business do you think is fair?
Why ask it
A bad review, a complaint, a former employee's view: every business has one that stings because it is partly true. A founder who can name it, and say what they did about it, earns more trust from a reader than any amount of praise.
People and routine
What does a normal working day look like for you, from the time you get up?
Why ask it
Routine questions are a staple because audiences like to compare their own day, so get real times and tasks. If what you hear sounds like the ideal day, ask how many days last week went that way.
How many people work in the business, and how has your own job changed as it grew?
Why ask it
Headcount is a fact your audience needs, so get the number and whether it counts part-timers and family. The second half brings out the move from doing the work to managing it, and some owners will admit they miss the earlier job. If they work alone, ask what they would hand over first.
What do you look for when you are hiring?
Why ask it
Lists of qualities are easy to give, so ask about the last person they took on and what tipped the decision. For a one-person business, ask instead which jobs they pay someone else to do and how they picked that person.
What decision do people in the business still argue about?
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.
When there is a big decision to make, who else is in the room?
Why ask it
The reply maps where the power in the company really sits: a co-founder, a spouse, an accountant, an investor. Sometimes it is nobody at all. When that is the case, find out whether it is by choice.
If I asked your staff what you are like to work for, what would they say?
Why ask it
People are franker here than when asked about their leadership style, and the reply often comes with a wince. If you can speak to an employee as well, their description next to the founder's own makes a strong pairing in the piece.
How do you keep the business from taking over the rest of your life?
Why ask it
Many founders will admit that they do not, and that admission is more use to you than a tidy rule about switching the phone off. Ask when the last full day off was and what they did with it.
Who do you go to for advice, and what is the best thing they ever told you?
Why ask it
A mentor, a parent, a group of other owners or an accountant all count. One exact sentence of advice, along with the situation it was given in, beats a paragraph about how much mentors matter.
What did you have to learn from scratch to run this?
Why ask it
Bookkeeping, selling, managing people, a piece of software, reading a contract: nobody arrives knowing all of it. How they picked it up, whether a course, a costly error or a patient friend, is practical detail a student audience can copy.
Lessons
What do you enjoy most about running your own business?
Why ask it
After a run of difficult questions this gives them somewhere pleasant to go. The reply is often neither freedom nor money. Listen for a small, particular pleasure, a regular customer or opening up in the morning, since that is what will sound true in print.
What are you proudest of so far?
Why ask it
Leave it open and notice what kind of thing they pick: a sales figure, a product, or a person. An employee who stayed ten years or a customer who came back says more about what the business is for than a line from the About page, and it gives you someone else to interview.
What does success mean to you now, and is that what it meant at the start?
Why ask it
Definitions tend to move from a revenue figure to something like time, staff who stay, or simply still being open. Ask whether they would say they have got there; the hesitation before the reply is worth describing.
What qualities do you think a person needs to do this?
Why ask it
On its own this produces a list of virtues, so turn it back on them: which of those did they have at the start, and which did the business force on them? What they say about themselves is the part to quote.
How has running a business changed you?
Why ask it
Give them a moment with this one. Good replies are specific and not always flattering: more patient with staff, quicker to say no, worse at switching off. If you only hear the flattering half, ask what the people at home would add.
If you could have the first year again, what would you do differently?
Why ask it
Asked loosely, this gets the reply that every mistake was a lesson. Tying it to the first year makes them choose: a lease signed too early, a price set too low, a partner taken on in a hurry. Find out what it cost them, in money or in months.
What advice do you hear repeated in your industry that you think is wrong?
Why ask it
It invites a real opinion, which a piece made of agreeable answers badly needs. Get the rule they follow in its place and one time it paid off, or the disagreement stays an attitude.
What advice would you give someone who wants to start a business?
Why ask it
Nearly every founder interview includes it, and the first reply is usually general. Ask what they would tell that person to do this week, with no money, and the advice turns into something your audience can act on.
Is there a book, a podcast or a person you would point a beginner to?
Why ask it
Take down the exact title or name and check the spelling before you leave. A recommendation with a reason attached is worth far more to your audience than a bare list, so get the one idea they took from it.
Knowing what it has taken, would you do it all again?
Why ask it
Nearly all of them say yes, so the interest is in how fast it comes and what conditions are attached: a long pause, or a yes followed by a but, is something you can describe in the piece as well as quote.
Looking ahead
What is next for the business over the coming year?
Why ask it
A year is close enough that the plans are real: a hire, a new product, a second site, a price change. Check before publishing whether anything they mention is still confidential, because founders sometimes announce things in interviews by accident.
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.
Where do you see the business in five years?
Why ask it
The standard closing question. Bigger is not the only reply: some owners want the same size with less of their own time in it, and some are building toward a sale. Write down what they say has to go right, since that is the part you can check back on later.
How long do you want to keep running the business yourself?
Why ask it
The five-year question is about the business. This one is about them, and it comes up far less often. Some will say until they drop and some have a date in mind. If they name a date, ask who knows about it besides you.
Would you ever sell the business, and what would have to be true?
Why ask it
Owners of small firms do not get asked this much, and some have thought about it more than they let on. Treat any figure or named buyer as off the record unless they tell you otherwise, and note whether the question lands as an insult or a relief.
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
Choosing from the list
- Nobody gets through all of these in one sitting. Half an hour rarely has room for more than ten or so once follow-ups are counted, so choose before you arrive and mark the three you will not leave without asking.
- For a class assignment, take two or three from each group so the write-up covers the start, how the business works, a setback and their advice. Read your brief first: some teachers set questions that must be included.
- For a podcast or video, favor the ones that ask for a scene: the first sale, the hardest week, the person who said no. A story holds a listener in a way that a question about strategy does not.
- For a written profile, lean on the business and the hard times, and collect the facts a reader needs along the way: the founding year, the headcount, what they sell and to whom.
- Open with the easy factual ones and hold the costly ones (what they gave up, what they are worst at, whether they nearly quit) for the second half, once they have decided you are listening.
Before you record
- If they have given interviews before, read or listen to the last two or three. 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.
- Ask before you press record and get the yes on the recording itself. Rules on recording a conversation differ from place to place, so check the ones that apply to you. 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 the whole list. 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
Count to three after an answer before you speak. People often fill a pause themselves, and what they add is frequently the part they had not planned to say.
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 the easiest claims to overstate and among the easiest to look up.
- Note where a story is theirs alone. If nobody else can confirm it, present it as their account rather than as fact.
- If your publication or your teacher allows it, read quotes and figures back to them for accuracy. Checking a fact is not the same as letting them rewrite the piece, so say which of the two you are offering.
- 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. An owner can only say yes to a request they can size up.
- Twenty minutes and six questions you actually care about beats an hour of a printed list.
- Ask about the ordinary running of the business as well as the founding story: who the customers are, where the money comes from, what a week involves. Check your marking criteria, since the assignment may ask for exactly that.
- Quote them accurately and send them the finished piece. It takes two minutes and it makes the next student's request easier.