Podcast Questions to Ask
Twenty questions for a podcast interview: how the guest actually got started, what the job turned out to be, the mistake that cost them something, the advice in their field they think is wrong, the decision they are still unsure about, and what they want a listener to do afterwards.
The questions
Open any question for the note
How do you explain what you do to someone who has never heard of your field?
Why ask it
It gets the guest speaking to your listener rather than to a peer, and it sets the vocabulary for the rest of the episode. If the answer is full of jargon, ask them to try again as if talking to a relative.
What was the first step that actually led here?
Why ask it
Asking for the first step gets a scene instead of a summary, and scenes are what listeners remember. Origin answers that begin with I have always been fascinated by are usually a rehearsed bio, so push for the specific year.
What did you expect this work to be like, and how was it different?
Why ask it
The gap between expectation and reality is where the useful detail sits, and it is a question nobody has media training for. It also gives newcomers to the field something concrete to weigh.
What is the part of this job you never get asked about?
Why ask it
Guests who have done many interviews have a stock set of answers, and this question deliberately steps outside it. Expect the boring or unglamorous side, which is often the most interesting material in the episode.
What is the biggest mistake you have made, and what did it cost?
Why ask it
The second half stops this becoming a humble-brag about learning and growth. If the cost is not named, ask again: money, a job, a relationship, two years. That is what makes the story land.
What is something you used to believe about your field that you no longer do?
Why ask it
It rewards guests who have actually updated their thinking and exposes those who have not moved in a decade. Follow up by asking what changed their mind, since the mechanism is more instructive than the conclusion.
What do most people get wrong about your work?
Why ask it
Reliable material because every field has one persistent misconception and practitioners are usually itching to correct it. It also gives you a natural title or clip for the episode.
What advice gets repeated constantly in your field that you think is wrong?
Why ask it
This produces the disagreement that makes an episode worth listening to. Ask who it works for and who it fails, so it lands as an argument rather than a complaint.
What is a habit or routine that genuinely changed how you work?
Why ask it
Ask for one and for the before and after, or you will get a morning routine list. The useful answers are usually small and specific: a weekly review, writing before email, a rule about which meetings to refuse.
What does a bad day look like for you?
Why ask it
It undercuts the polished version of a career without asking anyone to confess anything. Listeners in the same line of work recognize themselves in these answers more than in any success story.
Who taught you the most, and what exactly did they show you?
Why ask it
The word exactly is doing the work. Without it you get a tribute; with it you get a transferable technique, which is the part a listener can use tomorrow.
What is the last thing you changed your mind about because of evidence?
Why ask it
It separates people who follow the work from people who defend a position. A guest who cannot produce an example is telling you something useful about how they think, and the pause itself is worth keeping in the edit.
What are you working on right now that is not finished?
Why ask it
Unfinished work gets described with more energy and less polish than a completed project. It also dates the episode in a way that gives listeners a reason to follow what happens next.
What decision are you still not sure you got right?
Why ask it
More productive than asking about regrets, because it invites live thinking rather than a settled verdict. Give the guest room here and resist filling the silence while they work it out.
What do you turn down, and how do you decide?
Why ask it
Anyone with a full calendar has a filter, and describing it reveals their real priorities more accurately than any statement of values. It is also practical advice that listeners can copy.
What is a book or piece of work you keep going back to?
Why ask it
Ask what they return to rather than what changed their life, which gets a predictable list. Follow up on which part they reread, because the specific chapter tells you what they are still working on.
What is a question you wish interviewers would ask you?
Why ask it
Frequently the best two minutes of an episode, because the guest has been waiting to say something. Let them answer their own question fully before you move on.
What would you be doing if this had not worked out?
Why ask it
It gets at how contingent the career felt from inside, which is reassuring to hear for anyone earlier on. Guests who insist nothing else was possible are usually telling a story after the fact.
What are you paying attention to that most people in your field are not?
Why ask it
Better than asking for predictions, since it asks what they are watching rather than what will happen. If the answer is a widely covered trend, press for something they noticed themselves.
What do you want someone listening to actually do after this?
Why ask it
A closing question that produces one usable instruction instead of a summary. If the answer is to keep an open mind, ask for something a listener could do this week.
Running the Interview
Practical guidance for the conversation itself
Preparation That Shows Up in the Audio
Listen to one of their other interviews, not just their bio
You will hear their three stock answers, and you can then deliberately avoid asking the questions that trigger them. It is the cheapest way to make an episode sound different from every other appearance the guest has made.
Send topics, not questions
A guest who has seen the exact wording tends to arrive with a prepared answer and reads it out. Sending three or four areas gives them time to think without letting them rehearse sentences.
Write eight questions and expect to use five
The best material usually comes from following an answer rather than from the next item on your list. Order them so the two you most want are in the middle, when the guest has warmed up but is not yet watching the clock.
While You Are Recording
- Ask one question at a time. Two-part questions get the second half answered and the first half forgotten, and the interesting half is almost always the first.
- When an answer is abstract, ask for the last time it happened. A named week and a real outcome will always edit better than a principle.
- Leave three seconds after they stop. Guests routinely add the honest sentence in that pause, and the pause disappears in the edit anyway.
- If a guest gives you a rehearsed answer, thank them and ask the part they left out. Naming it politely usually resets the conversation.
- Follow the story that seems slightly off-topic. The tangent is often the reason the episode gets shared.
- Say the number back when a figure or date is mentioned. It confirms accuracy and saves you a fact-check later.
- Ask permission before pressing on anything painful, and mean it. A guest who trusts you will go further than one who feels cornered.
Closing and Afterwards
- Ask at the end whether there is anything they wanted to say and did not. This is where guests often produce the strongest thirty seconds of the recording.
- Confirm on the recording how they want their name and role described, spelling included. It saves an email and prevents a correction after publication.
- Check whether anything they said should be cut. Guests rarely ask for much, and the goodwill makes the next introduction easier to get.
- Note the timestamps of the two moments you would clip while it is still fresh. Finding them later takes three times as long.
- Send the episode link with one line about the part you thought was strongest. Guests share episodes that were listened to attentively.
- Keep a list of questions that produced unexpected answers, and of the ones that always fall flat. That list is worth more after twenty episodes than any template.