4 months ago•

Interview question bank organized by guest type for podcast and long-form interviews

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Prompt

You are a veteran long-form interviewer who has hosted on shows like Lex Fridman, Huberman Lab, and Diary of a CEO. Build me a reusable interview question bank organized by guest archetype for a [show_format] show focused on [show_theme].

For each of these guest archetypes — [archetype_list] — produce:
1. A one-line "what makes this guest interesting" frame
2. Five opening questions (warm-up, disarming, builds rapport)
3. Five deep-dive questions (the ones that produce viral clips)
4. Three contrarian / challenge questions (press without being hostile)
5. Three closing questions (reflective, shareable, stickable)
6. One "do not ask" trap question — why it always fails with this archetype

Each question should be phrased the way a real interviewer would say it out loud — not written-language formality. No generic questions like "tell me about yourself." Every question must have a specific angle.

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You are a veteran long-form interviewer who has hosted on shows like Lex Fridman, Huberman Lab, and Diary of a CEO. Build me a reusable interview question bank organized by guest archetype for a [show_format] show focused on [show_theme]. For each of these guest archetypes — [archetype_list] — produce: 1. A one-line "what makes this guest interesting" frame 2. Five opening questions (warm-up, disarming, builds rapport) 3. Five deep-dive questions (the ones that produce viral clips) 4. Three contrarian / challenge questions (press without being hostile) 5. Three closing questions (reflective, shareable, stickable) 6. One "do not ask" trap question — why it always fails with this archetype Each question should be phrased the way a real interviewer would say it out loud — not written-language formality. No generic questions like "tell me about yourself." Every question must have a specific angle.

Example output

# Interview Question Bank — Long-Form Podcast on Builders & Creators ## ARCHETYPE 1: THE TECHNICAL FOUNDER **Frame:** Someone who solved a problem by building something nobody asked for, and then the world caught up. **Opening questions:** 1. Before the company existed, what was the specific moment you realized the thing you were doing at your job was broken? 2. What did you build first — the thing you shipped, or a version of it nobody ever saw? 3. When you look at your earliest code or first prototype now, what makes you cringe? 4. Who was the first person outside your head you told about this idea, and what did they say? 5. What was on your screen the night you decided to quit your job? **Deep-dive questions:** 1. Walk me through the exact day you realized this was bigger than you expected — not the metrics, the feeling. 2. What's a technical decision you made early that you'd defend today even though every advisor told you it was wrong? 3. When did you stop being the best engineer in the room, and how did you handle that? 4. Tell me about the hire who almost broke the company. 5. What's the thing you'd only say about this industry if you were off the record? **Contrarian questions:** 1. A lot of people listening are building the same kind of thing and failing. What are they doing that you didn't? 2. You've said [public claim] — but the data I looked at suggests the opposite. What am I missing? 3. If this company disappeared tomorrow, who would actually be worse off? **Closing questions:** 1. What advice do you give now that you would have punched yourself for giving five years ago? 2. What's a question you wish more people asked you, and what's the answer? 3. If this conversation is the only thing someone ever hears from you, what do you want them to walk away knowing? **Do not ask:** "What's your morning routine?" — Technical founders either don't have one or have a performative one. Either way, the answer is boring and kills momentum. ## ARCHETYPE 2: THE CREATIVE ARTIST **Frame:** Someone whose work has an instantly recognizable fingerprint. **Opening questions:** 1. When you started, whose work were you openly copying? 2. What was the first piece you made that felt like yours, not a version of somebody else's? 3. What do you do in the first 15 minutes of a workday? 4. Describe the worst piece of feedback you got early, and why you can still quote it. 5. What's a tool or material you're using right now that nobody else seems to have figured out? **Deep-dive questions:** 1. What's the piece the audience loves that you privately hate? 2. Walk me through the decision to release something you weren't ready to show. 3. When did you realize you had a "style" — and did you immediately try to break it? 4. What's a collaboration that changed the way you see your own work? 5. Tell me about a creative dry spell and what actually ended it — not what you told people ended it. **Contrarian questions:** 1. A lot of your fans say your recent work is a departure. Are they right? 2. You've talked about authenticity, but your output has a clear commercial pattern. How do you square that? 3. If you had to defend your worst-reviewed piece in court, what's the argument? **Closing questions:** 1. What's a piece of craft knowledge you'd only share with someone at your level? 2. What do you want your work to be doing when you're not around to explain it? 3. What's the question about this work that nobody asks — and what's the answer? **Do not ask:** "Where do you get your inspiration?" — Artists have answered this 10,000 times. The reply is always rehearsed and never surprising.

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