Entrepreneur Questions to Ask
Twenty questions about method, for when you are building something yourself and want to know how another founder actually operates rather than how they got started. They cover testing an idea before building it, deciding what not to do, running a week, reading the numbers and choosing who to take advice from. For the founding story and the early years, the standard questions to ask an entrepreneur set covers that ground.
The questions
Open any question for the note
How do you decide an idea is worth your next three months?
Why ask it
This is the filter that shapes everything else they do. Ask for the last idea that failed the test as well as one that passed.
What do you do in the first week of looking at a new idea?
Why ask it
The first week is where method shows: calls, a landing page, a spreadsheet, a prototype, or nothing at all. It is directly copyable.
How did you test the idea before you built anything?
Why ask it
Look for whether money or a commitment changed hands before the product existed. Answers about positive conversations and encouraging feedback mean the idea was never really tested, only admired.
Who were your first ten customers, and how did you find them?
Why ask it
Almost always a network, a niche forum, or cold outreach at unglamorous volume. Founders who cannot recall the first ten by name usually had a longer pre-revenue period than the story suggests.
How do you price something you have never sold before?
Why ask it
Pricing method is rarely taught and every founder has invented one. Ask what evidence would make them change the number.
What did you believe at the start that turned out to be wrong?
Why ask it
Ask for the belief, not the lesson. Answers like assuming customers would care about the same feature they cared about are specific; answers about learning to persevere are a way of not answering.
How did you decide between raising money and funding it yourself?
Why ask it
The reasoning reveals what they were optimising for: speed, control, or a market with a land-grab dynamic. Founders who took investment because it was available rather than needed will usually admit it if you ask what the money was for.
What changed about your job after you took outside money?
Why ask it
Board meetings, reporting cadence, and the pressure to grow into a number rather than toward a customer. If the answer is nothing changed, either the round was small or the honest version is still coming.
What is your rule for killing something that is not working?
Why ask it
Without a rule, most projects run on far too long. The founders who have one can usually name the last thing it stopped.
Which failure changed how you actually work day to day?
Why ask it
The point is the change in process, not the failure. Ask what they now do differently on a Monday because of it.
How do you decide whether to hire, contract out, or leave a job undone?
Why ask it
This is the recurring resourcing decision in any small business. The answer tells you how they think about fixed cost and their own time.
What do you screen for in people now that you did not know to look for then?
Why ask it
Answers get very concrete after a few bad hires: tolerance for ambiguity, willingness to write things down, how someone behaves when the brief changes. Generic answers about culture fit mean the lesson has not landed yet.
What part of the job did you expect to hand off and still have not?
Why ask it
Usually sales, hiring, or the specific thing they are proud of doing well. Whatever it is, it is the current bottleneck in the company, and they know it.
How do you decide what not to do?
Why ask it
Founders with a real filter can name it in a sentence, often a customer segment or a revenue type they refuse. Founders without one describe being busy, which answers a different question.
What does your week actually look like, hour by hour?
Why ask it
Asking for the real timetable rather than the ideal one exposes where the hours go. Compare it with what they said their priorities were.
What number do you look at first in the morning?
Why ask it
Cash, pipeline, active users, churn, or nothing at all. The choice tells you what stage the company really is at and whether the founder is running it on instrumentation or on instinct.
Which competitor do you actually pay attention to, and why that one?
Why ask it
The named competitor is often not the obvious one, and the reason usually reveals the real basis of competition, whether that is distribution, price, or a single feature. Dismissing all competitors is a warning sign in itself.
What do customers ask for that you have decided not to build?
Why ask it
This is where product strategy actually lives. A founder who can explain a refusal, with the reasoning and the cost of it, has a strategy; one who lists everything on the roadmap does not.
How do you decide whose advice to take?
Why ask it
Founders receive far more advice than they can use. The filter they apply is more useful to you than any single piece of advice they repeat.
What advice do you give that people never take?
Why ask it
A better closing question than asking for advice directly, because it produces the thing they believe most and have watched be ignored. Expect something inconvenient, usually about charging money sooner or firing faster.
Getting a Real Conversation
Practical guidance for the conversation itself
How to ask so you get specifics
Ask for events, not philosophies
How do you approach hiring produces a paragraph anyone could have written. Who was your last hire and how did that go produces the story that contains the actual approach.
Ask what changed, not what they learned
Lessons are cheap to narrate. Behaviour changes are not, so following any failure story with what you do differently now separates the two.
Ask for numbers and accept ranges
First sale, headcount at the time, months of runway. Founders will often give a range rather than a figure, and a range is still far more useful than an adjective.
Do the homework and say so briefly
Knowing the product, the funding history and one recent announcement lets you skip the questions available on their website, which is what buys you the last ten minutes.
What goes wrong in these conversations
Treating one founder's path as the pattern
You are talking to someone who survived, and the people who took the same decisions and failed are not available for interview. Ask what they think was luck, and take the answer seriously.
Pitching your own idea in the first meeting
Asking a founder to evaluate your idea before you have earned the time turns a useful conversation into a short polite one. Ask how they tested theirs and apply the method yourself.
Asking for figures they cannot share
Revenue, margins, customer names and cap table details are often under obligation. Asking for the shape of the answer, whether revenue doubled or crept, gets you most of the information without the awkwardness.
Running out of time before the useful questions
Origin stories expand to fill whatever space you give them. If you have thirty minutes, spend ten on how they started and twenty on what they would do differently.
A workable structure for thirty minutes
- 1Two minutes: say who you are and what you are trying to decide, so they can aim their answers.
- 2Eight minutes: how they started and how they tested the idea before building.
- 3Ten minutes: the hard middle, near-failures, first hires, what they stopped doing.
- 4Five minutes: what their week looks like now and what number they watch.
- 5Three minutes: the advice people never take, then ask who else you should be talking to.
- 6Afterwards: send one specific thing you did as a result, which is what makes a second conversation possible.