Guest-Specific Podcast Interview Questions
A timed run of show for one podcast guest: reframed stock questions, fresh angles, follow-ups, a curveball, and clip-worthy moments.
Before & after
Same prompt, same agent — the only difference is the skill.
I'd be happy to help you create interview questions for your tech entrepreneur guest. To make sure the questions are the best fit, could you tell me more about your podcast's focus? For instance, are you interested in questions about their personal journey, their business strategy, or their predictions for the industry? What's your podcast's tone - conversational, serious, playful? Also, what's your audience most interested in hearing? With those details, I can suggest some great questions that would work well. Alternatively, here are some general tech entrepreneur interview questions that often engage audiences: Can you tell us about your background? What's your biggest challenge? What advice do you have for aspiring founders? These are solid conversation starters.
INTERVIEW QUESTIONS FOR TECH ENTREPRENEUR OPENING (Sets tone, builds rapport) • Tell us about the non-tech event that shaped your thinking about product design • Most people don't know you spent two years in Southeast Asia before launching. How did that change you? BUSINESS NARRATIVE (Core story) • Walk us through the exact moment you realized your first product wasn't working • You could have raised Series B six months earlier. Why did you wait? What did that teach you? AUDIENCE INSIGHT (Specific to your niche) • For founders listening who've just hit product-market fit, what's the one mistake you wish you'd known to avoid? FORWARD-LOOKING • If you woke up five years from now and your company was 100x bigger, what would have to have happened? CLOSING (Memorable) • What's the skill nobody teaches in business school that you use most? VOICE NOTE: Questions assume conversational tone, rapid follow-ups on emotion, minimize yes/no responses. Build on guest's answers rather than reading sequentially.
About this skill
Your guest has done 80 podcasts and has a polished answer for every question you were going to ask. You get the origin story, the framework and the advice-to-founders line, and your episode sounds like all the others. This skill builds a question plan for that one guest. It is designed to get answers they haven't given anywhere else, in an order that builds.
What it does
- Lists the guest's "burned" questions, the ones with rehearsed answers, and reframes each one so the canned answer no longer fits
- Finds the under-explored material between the guest's public milestones and makes it the spine of the episode
- Writes short, concrete, one-question-at-a-time prompts with 2-3 follow-ups for when the guest gives a short answer
- Orders the questions into an arc (cold open, build, tension, curveball, land, close) sized to your runtime, with must-ask questions flagged
- Marks 2-3 clip-bait questions for your editor and plans how to handle sensitive topics, including an exit ramp
- Reviews a question list you paste in, marking each one KEEP, SHARPEN or CUT, and rewrites the weak ones
What you get
A ready-to-use run of show with timing markers, follow-ups, what each question unlocks, and a cut list for when time runs short. Every fact about the guest is tagged by source, so nothing unverified ends up being read on mic.
Best for
Interview podcast hosts and producers prepping repeat-circuit guests such as founders, authors and experts on a promo tour. Also useful for anyone whose episodes keep coming out flat or predictable.
SKILL.md preview
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name: guest-specific-podcast-interview-questions
description: Builds a podcast interview plan for one specific guest. It maps the questions the guest has answered to death, finds under-explored angles between their public milestones, and arranges short, concrete questions with follow-ups, a curveball and clip-worthy moments, timed to the episode length. Use when the user says "write questions for my podcast guest", "I'm interviewing X next week", "my interviews feel generic", "guests keep giving me the same canned answers", "this guest has done 100 podcasts, how do I get something new", "review my question list", or "how do I bring up a sensitive topic without killing the vibe".
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