Fun Questions to Ask an Entrepreneur

Press Print this list for twelve fun questions for an entrepreneur, each with a line to write on.

Fun Questions to Ask an Entrepreneur

EntrepreneurAsked byDate

  1. Write the name of the person and the business at the top, with the date.
  2. Ask each question aloud and write the answer down as it is said.
  3. Skip any question. Nobody has to answer every line.
  4. Tick the answers you plan to quote, and read them back before you use them.
  1. What is the oddest item on your desk, and how did it get there?
  2. What did you name your first van, printer or computer?
  3. Which catchphrase of yours could be printed on a mug?
  4. Which machine at work seems to know when you are in a hurry?
  5. If your business were an animal, which would it be?
  6. What was the worst name on the list before you chose the real one?
  7. What would your auto-reply say if it told the whole truth?
  8. What would your company's theme tune sound like?
  9. Which chore do you do when you should be doing the paperwork?
  10. What is the best thing you have found in a delivery that you did not order?
  11. Which motto would you never print on the sign?
  12. How have people mangled the name of your business?

Next step Networking conversation starters

How it works

These fun questions to ask an entrepreneur open light: the honest job title, the name of the first van, the office snack. Five more groups cover the idea, the first customer, mistakes, a normal week and the start.

Read the full guide

Open light, then ask how it began

The page opens on twelve of the Just for fun questions; press Pick 12 new questions for the other twelve. The box under the button switches to another group, such as The idea or A normal week, and each of those shows its twelve questions together. Then press Print this list: each question prints with a line to write on.

Interesting questions to ask entrepreneurs

The first customer asks for stories with a person in them: who walked in, how they found the place, what they complained about. The example answers are invented, and they print on a last page you can leave out.

Questions and answers

What are deep questions to ask entrepreneurs?

The ones in Mistakes and what they taught: which mistake still shapes your decisions, what almost made you stop, which rule you made after a hard lesson. Ask one, then wait.

Is there a questions to ask an entrepreneur PDF?

Press Print this list and choose Save as PDF in your browser's print window. The sheet holds the questions you picked, each with a line to write on.

Do the questions ask about money?

No. Nothing asks what anyone earns, owes or is worth. The questions are about the idea, customers, mistakes and the working week, and the page gives no business, legal or career advice.

Who can I interview with this sheet?

Anyone who started something: a shop owner, a market stall holder, a family member with a small business, a founder visiting a class. No company or product is named in any question.

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All 84 questions

Just for fun 24

  • How do you mark the end of a good week? A walk around the block with an ice pop.
  • How does your family explain what you do when a neighbor asks? "Something with boxes."
  • How have people mangled the name of your business? The Sock Hospital. We sell shoelaces.
  • If the business had its own holiday, how would you mark it? Free shoelaces and a very small parade.
  • If your business were an animal, which would it be? A beaver. Busy, damp and always building.
  • What did you name your first van, printer or computer? The van is Gerald.
  • What did you use as a desk before you owned a desk? An ironing board. The height adjusts.
  • What is the best thing you have found in a delivery that you did not order? One mitten, and a note that said sorry.
  • What is the oddest item on your desk, and how did it get there? A trophy from a pie contest I never entered.
  • What is the oddest spot you have answered the business phone from? Halfway up a climbing wall.
  • What was the worst name on the list before you chose the real one? Bob's Things. I am not even called Bob.
  • What would the business's mascot be, and what would it wear? A pigeon in a hard hat.
  • What would you sell in a second shop that was nothing like the first? Kites.
  • What would your auto-reply say if it told the whole truth? Gone fishing. Really fishing.
  • What would your company's theme tune sound like? A kazoo marching band.
  • Which catchphrase of yours could be printed on a mug? "Nearly." As in, nearly done.
  • Which chore do you do when you should be doing the paperwork? Sweeping. The floor has never been cleaner.
  • Which job title would you give yourself if titles had to be honest? Chief Box Carrier.
  • Which machine at work seems to know when you are in a hurry? The label printer. It jams on purpose.
  • Which magic power would you spend on your inbox? Reading it by touching the screen once.
  • Which meeting could have been a paper airplane? The one about the font.
  • Which motto would you never print on the sign? "We will get to it."
  • Which plant at work has lasted the longest, and how? A cactus. It thrives on being ignored.
  • Which snack powers the business? Salted peanuts from the big jar.

The idea 12

  • How did the idea change between the first sketch and opening day? It began as an app and ended up as a van.
  • How did you choose the name of the business? From a list of forty, read aloud to my dog.
  • How did you know the idea was worth leaving something else for? Strangers kept asking when it would open.
  • What did you believe at the start that you no longer believe? That a good product explains itself.
  • What did you build first to test the idea? A paper sign-up sheet taped to a cafe wall.
  • What did you see other businesses doing that you wanted to do differently? Nobody answered the phone.
  • What is the smallest version of your business that could still run? Me, a folding table and a sign.
  • What problem were you trying to fix when the idea first came? I could never find a plumber on a Sunday.
  • Where were you when you first wrote the idea down? On a bus, on the back of a receipt.
  • Which idea did you drop before this one? A shop for left-handed tools.
  • Which part of the idea did you have to let go? Home delivery. It tripled the work.
  • Who heard the idea before anyone else, and how did they react? My sister. She said, "Who would want that?"

The first customer 12

  • How did the tenth customer arrive, and was that easier than the first? The first nine told people.
  • How did your first customer find you? A hand-painted sign on the sidewalk.
  • How do you find out what customers really think? I work the counter on Saturdays and listen.
  • What did you do on the day of your first sale? Took a photo of the receipt and went back to work.
  • What did your first customer complain about? The door was hard to open. They were right.
  • What do customers ask for that you do not offer? Gift wrapping, every December.
  • What do regular customers know that new ones do not? That the back shelf has the good stuff.
  • What do you do when a customer is unhappy? Call them myself the same day.
  • What surprised you about who your customers turned out to be? I planned for students and got grandparents.
  • Which customer taught you the most? The one who returned everything, with notes.
  • Which thank-you note or kind review did you keep? A postcard, still taped beside the register.
  • Who was your first customer who was not a friend or a relative? A man who walked in to ask for directions.

Mistakes and what they taught 12

  • How do you own up to an error in front of your staff? First thing Monday, with what I am changing.
  • What almost made you stop, and what kept you going? A winter with an empty shop. Then one regular came back.
  • What did a bad week teach you that a good week never could? Which jobs only I knew how to do.
  • What did you learn from someone who had done it before you? The baker next door showed me how she closes up at night.
  • What did you put off that belonged on day one? Writing down how things are done.
  • What do you do differently now because something once went wrong? I count the stock myself on Fridays.
  • What was your first big mistake, and how did you find out? I ordered a thousand boxes in the wrong size.
  • When did you say yes and wish you had said no? A huge order that ate every hour for a month.
  • Which early task got far more hours than it deserved? The logo. Nobody noticed.
  • Which mistake do you still think about when you make a decision? Saying yes to a deadline I could not meet.
  • Which mistake turned out to be lucky? A misprinted label that customers loved.
  • Which rule did you make for yourself after a hard lesson? I read every label twice before it goes to print.

A normal week 12

  • How do you decide what not to do this week? If it can wait a month, it waits.
  • How much of your week is the work you love, and how much is everything else? One day of making, four of email.
  • What do you do on the slowest day of the week? Fix whatever broke on the busiest one.
  • What is the first thing you look at on a Monday? The orders that came in over the weekend.
  • What piles up on your workbench as the week goes on? Sticky notes and one cold cup of tea.
  • What tells you on Friday that the week was worth it? An empty shelf where the new thing was.
  • Where do your clearest ideas about the business turn up? In the van between deliveries.
  • Which decision lands on you every single week? What to reorder and what to let run out.
  • Which morning is closed to meetings, and what happens in it? Tuesday. Phone off, door shut, real work.
  • Which notebook, board or tool runs your week? A paper planner with a rubber band around it.
  • Which small task do you refuse to delegate? Packing boxes. It helps me think.
  • Who do you talk to most between Monday and Friday? My supplier. We speak before breakfast.

Starting out 12

  • What did the business push out of your life at the beginning? Weekends, and my vegetable garden.
  • What did you forget to buy before you opened? A second set of keys.
  • What did your family think when you told them? They asked whether it came with free samples.
  • What small moment made the business feel real? A phone call asking for our opening hours.
  • What was the first thing you bought for the business? A secondhand label printer.
  • What was the weather, the crowd and your mood on opening morning? Rain, eleven visitors, and my mother at the door.
  • What was your job right before you opened? Driving a delivery route and taking notes.
  • What would you keep exactly the same if you began again? The kitchen table, and the secondhand label printer.
  • Where was your first workspace? The end of my kitchen table.
  • Which skill did you have to pick up fast? Spreadsheets, from videos at midnight.
  • Who turned up to help before you thought to ask? My neighbor, who lent a ladder and stayed all day.
  • Who was the first person you hired, and why them? A student who asked better questions than I did.
How this list was compiled

Written for this site on 2026-10-03 by the Game Night Generator editors: 84 questions to ask an entrepreneur, in 6 groups, each with one invented example answer that describes nobody. Own work; these are our suggestions, nothing was copied from another site and no fact is stated. No company, product or real person is named. Nothing asks what anyone earns, owes or is worth, and the page gives no business, money, legal or career advice. Licence: own work