Good podcast interview questions give the guest something concrete to recall: a moment, a decision, a mistake or a result. Start with one topic that matters to your listener, choose a few questions, and leave room for follow-ups. You do not need to get through all 35.
For a founder, that topic might be the first customer who changed the product. For a consultant, it might be how a project went off course and what they would do differently. A business owner could explain a decision about pricing, hiring or service. Choose an experience you can discuss openly and accurately.
Start small: choose five or six questions, including an opening and a closing. Keep the follow-ups nearby. If you already have a topic, skip to the editable interview brief.
Before you ask the first question
Decide what the listener should learn. “Tell us about your business” leaves the guest to choose a direction. “How did you work out what your first customer needed?” gives the conversation somewhere to begin.
- Read the guest’s public work. Find an idea or experience you can ask about specifically.
- Agree on the recording. Confirm how to pronounce their name, how you plan to use the recording and what is on the record.
- Share a theme and a few opening questions. Give the guest time to recall useful examples without asking them to memorize answers.
- Ask one question at a time. Let the answer finish, then follow the part that needs more explanation.
Use these questions with a human guest, or use them to prepare your own stories before someone interviews you. If you are still choosing a format, start with our guide to planning your first podcast episode.
Questions 1–6
Origin: start with a moment
For founders and entrepreneurs, an origin story becomes easier to follow when it starts with something that happened. Skip the full résumé and find a scene.
What was happening when you first noticed the problem your work now addresses?
Follow-up Where were you, and what made that moment stick with you?
What did your first attempt at solving it look like?
Follow-up What could that early version do, and what could it not do yet?
Who was the first person to take your idea seriously?
Follow-up What did they do that went beyond saying it sounded interesting?
Which part of your previous work turned out to be unexpectedly useful?
Follow-up Can you describe a situation where you used that experience?
What did you believe at the beginning that you no longer believe?
Follow-up What observation changed your mind?
When did this move from an idea you talked about to work you actually committed to?
Follow-up What did you put aside to make room for it?
Questions 7–12
Customer problem: look for behavior
Ask about a particular customer situation without identifying someone who has not agreed to be discussed. Separate what a person said from what they did.
Walk me through the last time you watched someone deal with this problem.
Follow-up What did they do before, during and after the difficult part?
How were people getting the job done before your product or service existed?
Follow-up What was inconvenient about that approach, and what worked well?
Which customer question made you realize you were explaining the wrong thing?
Follow-up How did you explain it the next time?
When has someone decided your offer was not right for them?
Follow-up What did that reveal about who you can help?
What have customers done that surprised you more than their feedback did?
Follow-up How did you check that it was a pattern rather than one unusual case?
What changed in your understanding of the problem after your first paying customer?
Follow-up Which part of that lesson might not apply to your next customer?
Questions 13–18
Decisions: show the tradeoff
For a business owner, a pricing, hiring or service decision can make a useful episode. Ask about the options available at the time, before the outcome was known.
Take me to a decision where two reasonable options pulled you in different directions.
Follow-up What would you gain and give up with each option?
What did you choose not to build, offer or take on?
Follow-up Who felt that choice most, and how did you explain it?
When have you changed a price, deadline or scope that someone was already expecting?
Follow-up What did you say in that conversation, and what happened next?
What information did you wish you had before a recent decision?
Follow-up How did you move forward while that information was missing?
Which decision looked small at the time but changed how you work?
Follow-up What is different in your day now because of it?
What would have to change for you to reverse a decision you still stand by?
Follow-up What specific signal would make you reconsider?
Questions 19–24
Failures: understand what broke
Make room for a modest mistake or an unresolved problem. A useful lesson does not require a dramatic confession or a tidy success story.
Tell me about an attempt that did not work the way you expected.
Follow-up What was the first sign that your expectation was wrong?
Which warning did you initially explain away?
Follow-up Looking back, what made it easy to dismiss?
When did your process make a problem harder to solve?
Follow-up What did you change in the process, rather than asking people to try harder?
What did an experiment fail to tell you, even after you had the results?
Follow-up What else might explain the outcome?
How did you handle a promise you could not keep?
Follow-up What did you communicate, and what could you actually put right?
What advice did you follow that turned out not to fit your situation?
Follow-up Which conditions would need to be different for that advice to help?
Questions 25–30
Practical expertise: make it usable
These questions suit consultants, practitioners and independent experts. Ask for a demonstration, a decision rule and a limit—not just a list of tips.
What is the first thing you look for when someone brings you this problem?
Follow-up Can you show how you would use that clue in a simple example?
Walk me through your approach to a recent situation you can discuss publicly.
Follow-up At which step did you need to use judgment rather than follow a checklist?
What does a beginner often mistake for progress in your field?
Follow-up What would you look for instead?
Which step do people tend to rush, and why does it matter?
Follow-up What is a practical way to tell whether that step is complete?
When would you tell someone not to use your usual method?
Follow-up What would you try first in that situation?
What could a listener try with the time and tools they already have?
Follow-up What should they notice afterward before deciding what to do next?
Questions 31–35
Reflection: leave a useful next step
Finish by connecting the story to the listener. Give the guest space to qualify a claim, name an uncertainty or correct a question.
What do you do differently now because of the experience we have discussed?
Follow-up What would someone watching you work actually see you do differently?
Which part of this story are you still trying to understand?
Follow-up What are you doing to learn more about it?
What might a listener misunderstand if they only heard the headline version of your story?
Follow-up What context would you want them to keep?
What should I have asked to make this conversation more useful?
Follow-up Where would you start answering that question?
What is one small thing a listener could try after this conversation?
Follow-up Who would that step help, and who should take a different approach?
The follow-up is where you find the story
When an answer stays broad, ask for one moment. When the guest describes a result, ask what they compared it with. When they offer advice, ask when it would not apply. You are helping the listener understand the answer, not trying to catch the guest out.
- 01 · A broad claim“We listened to customers.”A starting point. The listener still cannot picture what happened.
- 02 · Find the moment“Take me to the conversation that changed your mind.”Now you have a person, a situation and something at stake.
- 03 · Ask for evidence“What did you change afterward, and how did you tell whether it helped?”Separate what happened from what you think caused it.
Illustrative prompts. Follow the guest’s answer rather than asking every follow-up in order.
If the guest cites a number, clarify the time period, the baseline and other possible explanations. A result can be real without proving that one decision caused it.
A founder example: follow the detail that changes the story
Fictional teaching example. Mira and the business below are invented; this is not a customer story or an Alex recording.
Guest: “We learned that we needed to listen to customers.”
Host: “Take me to the conversation that changed your mind.”
Guest: “I was showing a repair-shop owner our scheduling dashboard. He kept returning to the appointment that hadn’t shown up that morning. I was talking about calendar views; he was thinking about an empty hour.”
Host: “What did you do differently after that conversation?”
Guest: “We paused the dashboard redesign and tried reminder messages. We still needed to find out whether reminders changed attendance or whether other things were affecting it.”
The useful part is the gap between what Mira was presenting and what the owner cared about. A follow-up about the test can explore what she learned, what she cannot yet conclude and what she would check next.
Turn five questions into an episode plan
Here is a filled outline using the fictional scheduling-software founder. It stays with one customer conversation instead of trying to cover the whole business. The question numbers refer to the list above.
For someone testing a business idea: how a customer complaint becomes a small test. Uses the fictional Mira example above.
- 00:00–02:00Frame the problemQ1 · What was happening when you first noticed the problem?Mira recalls an owner trying to fill a gap left by a missed appointment.
- 02:00–06:00Tell the customer storyQ7 · Walk me through the last time you watched someone deal with it.Ask what the owner tried before considering new software.
- 06:00–11:00Unpack the decisionQ13 · Which two reasonable options pulled you in different directions?Explore the choice between a dashboard redesign and a reminder test.
- 11:00–17:00Examine what remains uncertainQ22 · What did the experiment fail to tell you?Ask what else changed and what Mira would need to compare next.
- 17:00–20:00Give the listener a next stepQ35 · What is one small thing a listener could try?Observe one customer doing the job, then write down what you still need to learn.
Sample timings for practice, not an AI Podcaster session limit or a guaranteed duration. Give a useful story more room when it needs it.
Use the plan as a guide. Let the guest correct a premise, pause to think or spend more time on a useful story. You can skip a prepared question when the answer has already covered it.
Make your own interview brief
Write down the listener, the promise and five questions you want to explore. Add a concrete example you can discuss publicly. Edit the brief below, then copy it into your own notes.
Edits stay on this page. Nothing is uploaded or saved.
If you are preparing to speak with Alex, use this to organize your topic and examples. Alex prepares its own questions; this worksheet does not import a fixed script into the interview.
Common questions about podcast interviews
How many questions should I prepare?
For the practice plan above, five core questions leave space for follow-ups. Prepare a few optional prompts in case a topic runs short. The right number depends on the depth and length of the conversation, so do not treat the list as a quota.
What are good podcast questions for entrepreneurs and business owners?
Ask about an actual customer problem, an early attempt, a difficult decision and something the person now does differently. A concrete pricing, hiring or service decision often reveals more than a broad request for success tips. Use the origin and decisions sections as a starting point.
Should I send every question to the guest?
Share the topic, the intended listener and enough questions to help the guest prepare accurate examples. Agree on any boundaries beforehand. During the interview, listen for useful details and ask follow-ups rather than expecting a word-for-word script.
What if the guest gives a very short answer?
Pause, then ask for a specific example: “Can you walk me through the last time that happened?” If the guest does not want to discuss it, acknowledge that and move to another topic.
Can I use these questions to prepare for an AI interview?
Yes. Use them to recall stories and narrow your topic. Alex interviews you in real time and prepares its own questions. Your recording includes your voice and the AI host’s voice, with saved audio and a speaker transcript to review.
Finish with something the listener can use
Before publishing, review the recording for clear explanations, accurate claims and the boundaries you agreed on. A useful episode lets someone understand what happened and what they might try next.
For recording setup and a review checklist, see how to start a solo podcast.
Your experience is the starting point
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