You’ve read the papers. You’ve mapped the literature. You understand the debates. 📚

But the smartest people in the room aren’t always in the papers. They’re the practitioners, the insiders, the people who’ve been doing this for decades. The ones who know what actually works — not just what the studies say.

And you have a chance to talk to them. 🎙️

But here’s the problem: A bad interview is wasted access.

You ask surface-level questions. You get surface-level answers. You leave with nothing you couldn’t have found on Google. And the expert walks away thinking, “Why did I even agree to this?”

A good interview is preparation. It’s knowing what to ask, what to dig into, and what to let go. It’s understanding that the expert’s time is precious — and your questions better be worth it.

The good news? ChatGPT can help you prepare better questions, anticipate expert responses, and structure conversations that actually produce insights. Not generic questions. Questions that unlock what only this person knows. ⚡

📋 Table of Contents

• Prompt 1: The Expert Profile Builder
• Prompt 2: The Question Generator (Surface → Probe → Reflect)
• Prompt 3: The “What Would an Expert Say?” Simulator
• Prompt 4: The Knowledge Gap Interviewer (What Do They Know That No One Wrote Down?)
• Prompt 5: The Difficult Question Forge
• Prompt 6: The Follow-Up Question Generator
• Prompt 7: The Interview Debriefer (Extract Insights After the Call)

🎤 Prompt 1: The Expert Profile Builder

Best for:
Understanding who you’re talking to — their background, biases, and unique perspective. 👤

Act as a research strategist. Help me profile this expert before the interview. Expert's name and title: [Insert name/role] Expert's organization/affiliation: [Insert organization] Expert's known work (publications, talks, projects): [Insert what you know] Topic we'll discuss: [Insert topic] Create a PROFILE that helps me prepare: 1. THEIR PERSPECTIVE (2-3 sentences) - Based on their work, how do they likely see this topic? - What's their "thing" — the angle they always bring? 2. THEIR BIASES (1-2 sentences) - What might they be blind to? - What do they have a stake in? 3. THEIR JARGON (5-10 terms) - What language do they use? - What should I understand before the call? 4. THEIR INFLUENCE - Who do they cite? Who cites them? - Where are they in the intellectual food chain? 5. WHAT ONLY THEY KNOW (1-2 sentences) - What unique experience or access do they have that others don't? - Why this person specifically? 6. MY RELATIONSHIP TO THEM - Are we equals? Am I a student? Am I a peer? - How formal should I be? This helps me calibrate the conversation before it starts. 

⚙️ Technique Used:
This uses Interlocutor Modeling Prompting — understanding the person as much as the topic.

🎤 Prompt 2: The Question Generator (Surface → Probe → Reflect)

Best for:
Building a structured question set with depth, not just surface-level curiosity. 🧠

Generate a structured interview question set for this expert. Topic: [Insert topic] Expert's expertise: [Insert their specific angle or experience] My goal for this interview: [To understand X / To get specific insights on Y / To verify my hypothesis about Z / To uncover practical advice] Time available: [15 min / 30 min / 45 min / 60 min] Generate questions in three layers: LAYER 1: SURFACE QUESTIONS (Opening) - Warm-up, build rapport, establish context - 2-3 questions that are easy to answer - Establish why this topic matters RIGHT NOW LAYER 2: PROBE QUESTIONS (Depth) - Go beyond the surface - Challenge assumptions - Ask for specifics (examples, stories, data) - 3-5 questions that experts LOVE to answer LAYER 3: REFLECT QUESTIONS (Synthesis) - Ask for their big-picture take - Push for recommendations - What are they not saying? - 2-3 questions that make them think Also include: - 2 "DEATHBED" QUESTIONS (If you could only ask one thing...) - 1 "ELEVATOR PITCH" question (Summarize your view in 60 seconds) Format as a ready-to-use interview guide. 

⚙️ Technique Used:
This uses Funnel Prompting — moving from broad to deep to synthetic.

🎤 Prompt 3: The “What Would an Expert Say?” Simulator

Best for:
Stress-testing your questions before the interview — and predicting their answers. 🧪

Simulate how this expert might answer my questions. Expert's profile: [Insert profile from Prompt 1] My questions: [Insert your draft questions] For each question, simulate: 1. THE EXPERT'S LIKELY ANSWER (2-3 sentences) - Based on their known views, how would they respond? 2. WHAT THEY MIGHT THINK BUT NOT SAY (1 sentence) - What's the subtext? What are they holding back? 3. WHAT THEY MIGHT DISAGREE WITH IN MY QUESTION (1 sentence) - How might they challenge the framing? 4. A FOLLOW-UP THAT WOULD SURPRISE THEM (1 sentence) - What would make them pause and think differently? 5. MY BEST RESPONSE TO THEIR ANSWER (1 sentence) - How do I keep the conversation flowing? This helps me anticipate the conversation and prepare for where it might go. 

⚙️ Technique Used:
This uses Counterfactual Prompting — imagining conversations before they happen.

🎤 Prompt 4: The Knowledge Gap Interviewer (What Do They Know That No One Wrote Down?)

Best for:
Accessing tacit knowledge — the expertise that exists in heads, not in books. 🔍

Help me design questions that extract tacit knowledge from this expert. Topic: [Insert topic] What's known in the literature (from your review): [Insert 2-3 key things the literature says] What I suspect the expert knows that ISN'T in the literature: [Insert your guess — e.g., "how this actually works in practice," "what gets hidden in reports"] Design questions that uncover: 1. IMPLICIT KNOWLEDGE (What's second nature to them?) - "What do people get wrong about this?" - "What's the biggest myth in your field?" - "What's the thing that took you 10 years to learn?" 2. PATTERNS (What have they noticed that others haven't?) - "What patterns have you observed over time?" - "Who does this differently, and what do they do?" 3. EXCEPTIONS (What breaks the rules?) - "When does the conventional wisdom fail?" - "Tell me about the biggest failure you've witnessed." 4. FUTURE PREDICTIONS (Where is this heading?) - "What's the thing people aren't paying attention to?" - "In 10 years, what will we look back on and laugh about?" 5. UNWRITTEN RULES (What aren't you supposed to say?) - "What's the thing everyone knows but nobody talks about?" These questions are about what the expert has learned the hard way. 

⚙️ Technique Used:
This uses Tacit Knowledge Prompting — extracting what’s learned through experience, not study.

🎤 Prompt 5: The Difficult Question Forge

Best for:
When you need to challenge the expert — politely but directly. ⚔️

Help me craft difficult questions for this expert. Expert's known position or claim: [Insert their publicly stated view — e.g., "AI will replace 80% of jobs"] My respectful challenge (what I want to push on): [Insert your doubt — e.g., "I think that's overstated" or "That ignores human factors"] Or let me identify where they're most vulnerable: - Is there a known criticism of their work? - Do they have a blind spot? - Have they shifted their position over time? Craft 3 challenging questions that: 1. DON'T put them on the defensive (they'll shut down) 2. DO create productive tension (they'll think harder) 3. Show I've done my homework (they'll respect me) 4. Ask for evidence or reasoning (not just opinion) Template for tough questions: "I understand you've said X. But I've also seen Y [evidence/counterargument]. How do you reconcile that?" "It seems like your view depends on assumption Z. What if that's wrong?" "Your critics say W. What would you say to them?" Include a note on how to deliver these questions with the right tone — respectful but curious, not aggressive. 

⚙️ Technique Used:
This uses Confrontational Prompting (Soft) — challenging ideas without challenging the person.

🎤 Prompt 6: The Follow-Up Question Generator

Best for:
Going deeper when the expert gives a surface-level answer. ⬇️

Generate follow-up questions for this interview. Topic: [Insert topic] Likely surface answers I might get: [Insert 2-3 possible answers that are too vague or obvious] For each possible surface answer, generate 3 follow-up questions that: 1. ASK FOR SPECIFICS - "Can you give me a concrete example?" - "What did that look like in practice?" 2. ASK FOR EVIDENCE - "How do you know that?" - "What data would back that up?" 3. ASK FOR STORY - "When did you first realize that?" - "Tell me about a time that was true." 4. ASK FOR THE OPPOSITE - "When has that NOT been true?" - "What would someone who disagrees with you say?" 5. ASK FOR IMPLICATIONS - "So what does that mean for [other context]?" - "If that's true, then what else must be true?" Probe, probe, probe. The first answer is never the real answer. 

⚙️ Technique Used:
This uses Layered Inquiry Prompting — digging past the surface every time.

🎤 Prompt 7: The Interview Debriefer (Extract Insights After the Call)

Best for:
Turning raw interview notes into actionable insights before you forget them. 📝

Help me debrief and extract insights from this interview. Interview notes (paste your raw notes or transcript): [Insert your notes] Expert: [Insert name] Topic: [Insert topic] Extract from my notes: 1. THE BIGGEST SURPRISE (1-2 sentences) - What did they say that I didn't expect? - What challenged my assumptions? 2. THE MOST ACTIONABLE INSIGHT (1 sentence) - What can I actually DO with this information? 3. THE COUNTERINTUITIVE INSIGHT (1 sentence) - What did they say that goes against conventional wisdom? 4. THE QUOTE WORTH SAVING (1-2 sentences) - Exact words that capture their perspective perfectly 5. WHAT WAS MISSING (1 sentence) - What didn't they say? What should I follow up on? 6. MY ONE-PARAGRAPH SUMMARY (3-4 sentences) - If I had to tell someone what I learned in 60 seconds 7. NEXT STEPS - What do I do with this? - Who else should I talk to? - What should I read next? Also flag any claims that need verification — don't take everything they said as fact. 

⚙️ Technique Used:
This uses Post-Processing Prompting — extracting structure from raw notes.

🚀 Final Thoughts

An interview is a gift.

Someone is giving you their time, their attention, and their hard-won expertise. The least you can do is show up prepared — not just with questions, but with respect for what they know.

These prompts help you do that. They help you understand who you’re talking to, what to ask, how to dig deeper, and how to capture what you learned.

The best interviews aren’t about getting answers. They’re about understanding how the expert thinks — not just what they know.

Now go ask better questions. 🙌