Interview questions that get founders talking

Before the questions

The questions below are less important than how you ask them. Four rules hold for every one of them.

• One at a time. A list of twenty questions in a document gets twenty one-line answers. A single question in a message gets a paragraph.
• Ask for the event, not the theme. "Tell me about leadership" produces a definition. "Tell me about a time you had to let someone go" produces a story.
• Follow up once or twice, then move on. The first answer is usually the summary. The follow-up is where the detail lives. A third follow-up feels like an interrogation.
• Let them answer from their phone. A founder will reply to a WhatsApp message in a taxi. They will not open a form in a taxi.

The follow-ups given here are the ones we ask most often. If an answer already contains the detail, skip them.

Stories

A story is a thing that happened, with a before and an after. Most founders have dozens and have told none of them in writing.

1. What was the moment you knew the original plan was not going to work?
   If thin: Where were you? Who was in the room? What did you do that afternoon?
2. Tell me about a deal or a hire you regret.
   If thin: What did it cost, in money or months? What do you check for now that you did not then?
3. What is the closest the business has come to not making it?
   If thin: What was the number in the bank? What was the conversation at home?
4. Describe a customer conversation that changed how you think about the product.
   If thin: What did they say, as close to word for word as you can?
5. What did your first week look like after leaving your last job?
   If thin: What did you do on the Monday? What surprised you?
6. When did someone on your team do something that made you proud, and what was it?
   If thin: Did you tell them? What did you say?
7. What is a decision you made quickly that turned out to be right?
   If thin: What did you know that made it feel obvious? What did others think?
8. What happened the last time you were wrong in front of your team?
   If thin: How did you find out? What did you say to them?

Beliefs and opinions

The posts that get shared take a position. Founders hold strong views and soften them the moment a keyboard appears.

1. What does everyone in your industry believe that you think is wrong?
   If thin: What made you change your mind? What would it take to change it back?
2. What advice do you hear given to people at your stage that you would tell them to ignore?
   If thin: Who gives it, and why does it sound right?
3. What is a popular tool, method, or trend you have deliberately not adopted?
   If thin: What would have to be true for you to adopt it?
4. What do you think your competitors get right?
   If thin: Have you ever copied them? What happened?
5. What is something you believed strongly five years ago that you no longer believe?
   If thin: What was the evidence? When did it tip?
6. If a customer could only remember one thing about how you work, what should it be?
   If thin: Give me an example of a time it showed.
7. What will your industry look like in five years that almost nobody is preparing for?
   If thin: What are you doing about it now?

Lessons and mistakes

A lesson is a story with the moral attached. Ask for the mistake first; the lesson follows on its own.

1. What is the most expensive mistake you have made in this business?
   If thin: What was the price? How long before you noticed?
2. What did you learn about hiring the hard way?
   If thin: Who was the hire? What was the signal you missed?
3. What is a rule you now follow because of one bad experience?
   If thin: What was the experience? Has the rule ever been wrong?
4. What would you tell yourself the day before you started?
   If thin: Would you have listened? Why not?
5. What did you underestimate most in the first year?
   If thin: What did it look like when it caught up with you?
6. What is a thing you spent too long doing yourself?
   If thin: What finally made you hand it over? What changed after?

Frameworks and processes

A framework is how someone decides. Founders rarely know they have one until you ask them to walk through a real decision.

1. Walk me through the last significant decision you made. What did you weigh?
   If thin: What did you rule out, and why? Who did you ask?
2. How do you decide what to say no to?
   If thin: What is the most recent thing you said no to? What made it a no?
3. How do you run your week?
   If thin: What is fixed and what moves? What do you protect?
4. What questions do you ask in every interview with a candidate?
   If thin: What is a good answer and a bad answer to one of them?
5. How do you know when a project is going badly before the numbers show it?
   If thin: What was the last time you saw the signs? What did you do?
6. What do you look at first every morning, and why that?
   If thin: What would make you stop looking at it?

Craft and expertise

The specific, technical knowledge that a founder takes for granted is often the material their audience values most.

1. What is a question customers ask you that has a longer answer than they expect?
   If thin: Give me the long answer.
2. What do people get wrong when they try to do what you do without help?
   If thin: What does the mistake look like from the outside? What does it cost them?
3. What is a detail of your work that outsiders never see but that matters enormously?
   If thin: How did you learn that it mattered?
4. What is the difference between someone competent at this and someone excellent?
   If thin: Who is the most excellent person you have worked with? What did they do differently?
5. What has changed in your field since you started that most people have not caught up with?
   If thin: How do you know when someone has not caught up?

The person

Readers follow people, not companies. A few questions about life outside work give a writer texture to use sparingly.

1. What did you want to be at fifteen?
   If thin: Is there any of that in what you do now?
2. Who has had the most influence on how you work, and what did they teach you?
   If thin: Do they know? What would they say about how you turned out?
3. What is a book, talk, or piece of writing you keep going back to?
   If thin: What is the line you remember?
4. What do you do on a Sunday that has nothing to do with the business?
   If thin: How long have you done it? What does it give you?
5. What are you working on right now that you are not sure will work?
   If thin: What would success look like in six months?
6. What would you like to be known for in ten years?
   If thin: What is the first step toward that you have already taken?

What to do with the answers

An hour of good answers is worth nothing in a document nobody reads. Break each answer into the pieces a writer can use: a fact, a belief, a story, a lesson, a framework, a preference, a goal. Keep the client's original words next to each piece. Note which areas are covered well and which are still empty, and ask into the empty ones next time.

That is the work The Noticed Engine does after every answer, without anyone on your team doing it by hand. The questions are chosen from what the client has said and what is still missing, the follow-ups are asked when an answer is thin, and every item in the knowledge base links back to the message it came from.