01 · OPENERS
Opening questions that warm a guest up
The first question sets the tone. Make it easy to answer and specific to the guest, so they relax and the listener learns who they are.
- What are you working on right now that you are most excited about?
- How would you describe what you do to a ten-year-old?
- What did you want to be when you were growing up?
- What does a normal Tuesday look like for you?
- What is something people usually get wrong about you?
- How did you end up doing this?
- What is the best thing that happened to you this week?
- What were you doing five years ago?
- Who was the first person to take your work seriously?
- What question do you get asked most, and are you tired of it?
- What is on your desk right now?
- What did you change your mind about recently?
- What is a small thing you are weirdly good at?
- Where did you grow up, and how does it still show?
- What is the first thing you do in the morning?
- Which part of your job would surprise people?
- What are you reading or listening to?
- If this episode had a title, what would it be?
- What made you say yes to coming on?
- What should we definitely talk about today?
02 · STORY
Story questions that get specific moments
Ask for a moment, not a summary. "Tell me about a time" gets a story; "what is your approach" gets a speech.
- Tell me about the moment you knew this was what you wanted to do.
- What was the hardest week of your career?
- When did you nearly quit?
- What is a decision that looked wrong at the time and turned out right?
- Tell me about your first real failure.
- Who changed the direction of your life, and how?
- What was the best piece of advice you ignored?
- When were you most out of your depth?
- What was the first thing you made that you were proud of?
- Tell me about a conversation that changed your mind.
- What is a risk you took that people told you not to?
- When did luck play a bigger role than you admit?
- What was the turning point?
- What did your first year look like, honestly?
- Tell me about a time you were completely wrong.
- Which mistake taught you the most?
- What is a moment you wish you could relive?
- When did you feel like a fraud?
- What did success feel like the first time?
- What story do you tell at dinner parties?
03 · EXPERTISE
Questions that get useful expertise
These are the questions listeners came for. Push for specifics: numbers, steps, names of tools.
- What do beginners in your field get wrong most often?
- What would you do in your first 30 days if you started over?
- What is a common piece of advice you disagree with?
- What is the simplest thing that makes the biggest difference?
- What tools or habits could you not work without?
- How do you know when something is working?
- What does good look like, compared with great?
- What is overrated in your industry?
- What is underrated?
- What is changing in your field right now?
- What should someone ignore when they are starting?
- How do you decide what not to do?
- Walk us through how you actually do [task].
- What question should people be asking that they are not?
- What would you tell someone who is stuck at [common sticking point]?
- Where do you get your best ideas?
- What do you measure?
- How do you handle [common problem]?
- What is the most useful thing you learned this year?
- If listeners do one thing after this episode, what should it be?
04 · THE DEEP END
Deeper questions for the second half
Save these until the guest is comfortable. Ask, then wait. The real answer often comes after a pause.
- What are you afraid of?
- What do you want to be remembered for?
- What does success mean to you now, compared with ten years ago?
- What have you sacrificed for this?
- What keeps you up at night?
- What are you still trying to figure out?
- What do you believe that most people do not?
- Who do you want to make proud?
- What would you do if money did not matter?
- What has been the cost of getting here?
- What does rest look like for you?
- When do you feel most like yourself?
- What would you tell your younger self?
- What is something you have never said publicly?
- What are you proudest of that nobody sees?
- What do you hope changes in your field?
- What role has faith, family or community played in your work?
- What does a good life look like to you?
- What is still unfinished?
- What are you grateful for right now?
05 · CLOSERS
Closing questions that end on a high
Close with something quick and forward-looking, then make it easy for listeners to find the guest.
- What is one thing listeners should do this week?
- What are you excited about in the next year?
- Who should I have on the show next?
- What is a book everyone should read?
- What is the best investment you have made under 100 dollars?
- What question did I not ask that I should have?
- What is your favourite piece of advice in one sentence?
- What is something you are looking forward to?
- What is next for you?
- Where can people find you?
- What are you working on that we should watch for?
- What would you like listeners to take away?
- What is one thing you would change about your industry?
- What is the kindest thing someone has done for you?
- What podcast do you listen to?
- If you had one more minute, what would you say?
- Who deserves more credit than they get?
- What is your favourite word?
- What makes you laugh?
- What is the last thing that surprised you?
06 · FOLLOW-UPS
The follow-up is where the episode happens
Prepared questions get prepared answers. The best moments come from the second question. Three follow-ups work almost everywhere: "What do you mean by that?", "Can you give me an example?" and "What happened next?". For a full interview framework, see our podcast interview questions guide.
Good questions, great episode.
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