Good Questions to Ask an Entrepreneur
For a first proper conversation with someone who runs their own business, at an event, an introduction or a coffee you asked for. Every question here is one a founder can answer comfortably in front of strangers, so there is nothing about pay, cash reserves or regrets. Once you know each other well enough for that, the past the pitch set goes considerably harder.
The questions
Open any question for the note
What were you doing before this, and what made you leave it?
Why ask it
An easy opener that sets up everything else, because the push out of a previous job explains a lot about how much risk they were willing to carry. Founders who were pushed rather than pulled tell a different story from the one in their profile.
What problem were you trying to solve, and how did you know it was real?
Why ask it
The second half is the test. Look for evidence gathered before building: conversations, a spreadsheet someone was already paying to avoid, a process they had done manually for a customer. "Everyone I spoke to loved the idea" is not evidence.
How did you get your first ten customers?
Why ask it
This is the most transferable answer a founder can give, and it is almost always unscalable: personal contacts, a forum, cold calls, one conference. Anyone describing a marketing channel here has skipped from ten to ten thousand.
How did you fund the first year, and what did it cost you?
Why ask it
Ask about the cost as well as the source. Savings cost time, loans cost sleep, investment costs control, and a founder who describes only the amount raised has left out the part that shaped their decisions since.
What does a normal week look like now?
Why ask it
Expect the answer to be mostly meetings, hiring and other people's problems rather than the work they started the company to do. The gap between that and the founder mythology is the single most useful thing to hear.
What did you spend money on early that you would not spend again?
Why ask it
Specific and easy to answer honestly: an office, a rebrand before there was a product, an agency, custom software that a spreadsheet could have handled for another year. Cheaper to hear than to learn.
What part of the business surprised you most in the first year?
Why ask it
A friendly version of asking what went wrong, and one most founders answer with a story. It gives them the choice of how much to say.
How do you decide what to work on when everything looks urgent?
Why ask it
Look for a mechanism rather than an attitude: a weekly review, one metric, a rule about not starting anything new mid-month. Founders without one tend to describe their week as reactive when asked the previous question.
Who was your first hire, and what did you misjudge about hiring?
Why ask it
First hires are frequently wrong in a predictable direction: too senior, too junior, a friend, a generalist when a specialist was needed. The correction they describe is a rule you can borrow.
How do you decide whether to hire someone or wait another quarter?
Why ask it
Reveals how they think about cash against capacity. Answers that involve a trigger, such as a defined workload or a revenue threshold, are more informative than answers about finding great people whenever you can.
What was the first thing you did that made the business feel real?
Why ask it
Registering a name, a first invoice, a first employee. It is a warm question and it dates the beginning properly.
What part of the business are you most pleased with right now?
Why ask it
Asking what is going well is not an obvious opener but it produces detail, because founders rarely get asked. Follow up on why that part works.
How do you tell a slow start from a bad idea?
Why ask it
The hardest judgement in early business and one where honest founders admit they got it wrong at least once. Listen for a leading indicator they watch rather than a statement about persistence.
What did you have to stop doing yourself, and how did handing it over go?
Why ask it
Usually badly the first time, and the story of that is more useful than any principle about delegation. Ask what broke while it was being handed over.
What part of the job did nobody warn you about?
Why ask it
Answers tend to be administrative or emotional rather than strategic: employment law, chasing invoices, being the person everyone brings bad news to. This is the texture of the job that no case study covers.
What advice did you take that turned out to be wrong for you?
Why ask it
Invites disagreement with received wisdom, which is where experienced founders are most worth listening to. Common targets are raising early, hiring ahead of demand, and growing before the product held together.
What do you enjoy least about running your own business?
Why ask it
Softer than asking about bad weeks, and it still gets an honest answer about admin, isolation or chasing invoices. Most founders answer this one readily.
What would you want more of if the day had another two hours?
Why ask it
A gentle way to find the constraint without asking what is broken. The answer usually names the real bottleneck anyway.
If you started again tomorrow, what would you do in a different order?
Why ask it
Better than asking what they would change, because sequencing is where most of the avoidable damage happens: hiring before revenue, building before selling, raising before knowing what to spend it on.
What would you tell someone thinking of leaving a salaried job to do this?
Why ask it
Best asked last, once the practical answers are on the table, because it will be grounded in what they have just described rather than in the encouraging line they give at events. Ask what they would tell that person to do first.
Getting a founder's real answers
Practical guidance for the conversation itself
Getting the conversation at all
- Ask for a specific, short slot and name the topic. "Twenty minutes on how you found your first customers" gets accepted far more often than a request to pick their brain.
- Say what you have already done. Founders answer questions from someone who has started something, however small, differently from questions asked out of general curiosity.
- Do not ask them to be your mentor in a first conversation. Ask one question, act on the answer, and come back with the result.
- Come with three questions, not twelve, and send them in advance if the meeting is scheduled.
Pushing past the pitch
- Ask for the first instance, not the current process. How they got customer number three is useful; how their sales team is structured now is not, unless you have a sales team.
- Ask what it cost. Every decision a founder describes had a price in cash, time, equity or relationships, and the price is the part usually left out.
- When an answer sounds like a case study, ask what happened in the month before it worked. That is where the real sequence lives.
- Ask about the thing that is hard right now rather than the thing they overcame. Present-tense problems get much more honest answers.
What not to ask
- "What is your revenue?" as an opener. Ask what part of the business makes money instead, and let them choose how specific to be.
- Pitching your own idea unsolicited, or asking them to sign a confidentiality agreement before you describe it.
- "Can you introduce me to your investors?" in a first conversation. Introductions are their credibility, not their business card.
- Anything that assumes the work is glamorous, or that treats the company as though it were already the outcome.
- Asking for a job in a conversation you requested as a chance to learn.
What to do with the answers
- 1Write the notes up within an hour, separating what they did from what they concluded. The actions transfer between businesses far better than the lessons do.
- 2Pick two things to act on this month and ignore the rest. A list of twenty insights produces nothing.
- 3Discount anything that only worked because of a condition you do not have: a market at a particular moment, an existing audience, a co-founder who could work unpaid for a year.
- 4Send a short note a few weeks later saying what you tried and what happened. It is the thing most likely to turn one conversation into a continuing one.