01 · HOW TO ASK
Deep questions need a runway
Nobody answers "what are you most afraid of?" well in the first two minutes. Start light, earn trust, and save the heaviest question for the second half. When a guest gives a short answer, stay quiet for three seconds. Most people fill the silence with the real answer.
Tell guests before you record that they can ask you to cut anything. People share more when they know they are not locked in.
- Warm up with two easy questions first
- Ask one deep question, then follow up twice before moving on
- Share a short answer of your own to show it is safe
- Agree that anything can be cut after the recording
02 · IDENTITY
Questions about who they are
- What do most people get wrong about you?
- Which three words would your closest friend use to describe you?
- What part of yourself took the longest to accept?
- When do you feel most like yourself?
- What value would you never trade, even for a lot of money?
- What is a label people gave you that you have outgrown?
- What are you still trying to prove, and to whom?
- What does success mean to you now, compared with ten years ago?
- What is something you believe that most people around you do not?
- If you lost your job title tomorrow, how would you introduce yourself?
03 · GROWING UP
Questions about where they came from
- What did your family teach you without ever saying it?
- Who was the first adult who really believed in you?
- What did you want to be at ten, and how close did you get?
- What is a childhood memory that still shapes your choices?
- What rule from your house growing up do you still follow?
- What did you have to unlearn when you left home?
- What were you afraid of as a kid that seems funny now?
- What did your parents get right that you only noticed later?
- Where did you feel most at home as a teenager?
- What would your younger self be surprised by today?
04 · WORK
Questions about work and purpose
- What work would you do even if nobody paid you?
- When did you last lose track of time doing something?
- What is the hardest professional decision you have made?
- What did a failure teach you that a success never could?
- What are you building that will outlast you?
- When did you nearly quit, and what kept you going?
- What advice did you ignore that turned out to be right?
- What is a skill you are quietly proud of?
- How do you know when something is finished?
- What would you tell someone starting exactly where you started?
05 · RELATIONSHIPS
Questions about the people in their life
- Who has changed your life most, and do they know it?
- What does a good friend do that most friends do not?
- What is a relationship you wish you had handled differently?
- How do you like to be loved?
- Who do you call first with good news?
- What have you forgiven that you thought you never would?
- Which conversation are you still putting off?
- What did a hard breakup or falling out teach you?
- Who do you admire that you have never told?
- What do you hope people feel after spending time with you?
06 · LOOKING AHEAD
Questions about regret, time and the future
- What is a risk you are glad you took?
- What is one regret you have made peace with?
- What would you do differently if you started your twenties again?
- What are you most grateful for right now?
- What do you want the next five years to feel like, not look like?
- What is something you keep saying you will do one day?
- What scares you about getting older, and what excites you?
- What do you want to be remembered for?
- What question do you wish people asked you more often?
- If this were your last interview, what would you want to say?
Say it once. Cut what you need to later.
Record the conversation, then remove anything a guest regrets by deleting it from the transcript in Hilite.