Podcast Interview

Why This Matters: Most podcast interviews are forgettable because hosts ask the same questions and accept surface-level answers. NPR-trained interviewers and Tim Ferriss have developed techniques that consistently produce the "good tape" that makes episodes shareable and memorable.

What Claude Does vs What You Decide

What This Skill Does

1. Designs interview questions for story extraction - Questions that get narrative, not bullet points
2. Prepares comprehensive guest research - Know enough to ask unexpected questions
3. Creates psychological safety - Techniques for making guests vulnerable
4. Navigates difficult moments - How to redirect, follow up, and challenge respectfully
5. Identifies and pursues good tape - Recognizing when to dig deeper

How to Use

Prepare for an Interview

Help me prepare for a podcast interview with [guest name].
They are known for: [brief background]
Episode angle/theme: [what you want to explore]
Length: [target runtime]

Design Better Questions

I'm interviewing [guest type] about [topic]. Help me design questions that get stories, not just information.

Improve Existing Questions

Review these interview questions and suggest improvements:
[paste questions]

Instructions

When preparing and conducting interviews, follow this methodology:

Step 1: Deep Research Phase

Before writing a single question, immerse yourself in your guest.

## Research Checklist

**Primary Sources** (1-2 hours minimum):
□ Read/watch their most substantial long-form content
□ Their book, keynote, or signature work
□ Previous podcast appearances (note what's been asked before)
□ Recent social media activity (what are they thinking about NOW?)

**Secondary Sources** (30-60 min):
□ Wikipedia/bio for career arc and timeline
□ Company/project announcements
□ Industry news involving them
□ Interviews with people who've worked with them

**Look For**:
- Contradictions between what they say and do
- Topics they're NEVER asked about
- Recent changes in their thinking
- Personal moments that shaped their professional life
- The question you're dying to ask

Tim Ferriss's Rule: "I try to find the question they've never been asked that they'd love to answer."

Step 2: Design Questions for Story, Not Information

The difference between a mediocre and great interview is the type of questions asked.

## Question Types Hierarchy

**AVOID - Information Questions** ❌
- "What do you do?"
- "How did you get started?"
- "What advice would you give?"
→ Gets: Rehearsed talking points

**BETTER - Scenario Questions** ✓
- "Take me to the moment when..."
- "Walk me through the day..."
- "What was going through your mind when..."
→ Gets: Specific memories, sensory details

**BEST - Emotional Truth Questions** ✓✓
- "What scared you most about that decision?"
- "What did you learn that surprised you?"
- "What's the thing about [topic] that most people get wrong?"
→ Gets: Authentic reflection, vulnerability

Step 3: Structure Your Question Arc

Don't just list questions—design a journey.

## Interview Arc Template

**Opening (5-10 min)**
Purpose: Establish rapport, get them talking
- Start with something CURRENT (not their origin story)
- Show you've done your homework
- Ask about something specific and recent
- Example: "I saw your tweet last week about [X]. What prompted that?"

**Middle - Act 1 (10-20 min)**
Purpose: Understand the journey
- Key inflection points
- Decisions that shaped their path
- "What most people don't know about that period..."
- Follow unexpected threads

**Middle - Act 2 (15-25 min)**
Purpose: Go deep on the main topic
- The questions you MUST ask
- Challenges to their public positions
- "How do you reconcile X with Y?"
- The uncomfortable but important questions

**Closing (5-10 min)**
Purpose: Synthesis and takeaways
- What they're working on now
- What they'd do differently
- One piece of advice (but make it specific)
- The question you're afraid to ask

Step 4: Master the Follow-Up

The best material comes from following up, not from prepared questions.

## Follow-Up Techniques

**The Silence**: Say nothing after they finish. Count to 5. They'll fill it with gold.

**The Echo**: Repeat their last few words as a question.
Guest: "...and that's when I knew it was over."
You: "You knew it was over?"

**The Dig**: "Tell me more about that."

**The Redirect**: "Let's go back to something you said earlier..."

**The Challenge**: "Some people would say [counter-argument]. How do you respond?"

**The Feeling**: "How did that make you feel?" (Use sparingly but powerfully)

**The Unexpected**: "That's not what I expected you to say. Why...?"

NPR Rule: Prepare 2x more questions than you'll need, but be ready to throw them all out if the conversation goes somewhere better.

Step 5: Create Psychological Safety

Vulnerability requires safety. Build it intentionally.

## Before Recording

- Share YOUR vulnerabilities about the topic
- Be explicit about your goals: "I want this to be a real conversation"
- Remind them they can say "off the record" anytime
- Start with low-stakes questions to warm up
- Match their energy and pace

## During Recording

- React authentically (laugh, express surprise)
- Share related personal experiences briefly
- Make eye contact (even on video calls)
- Nod, use "mm-hmm" to show engagement
- Never look at your phone or notes while they're sharing something vulnerable

## After Difficult Moments

- Acknowledge what they shared: "Thank you for being so honest about that."
- Give them an easy question to recover
- Return to vulnerable topics gently if needed

Step 6: Navigate Difficult Moments

## When They Give a Non-Answer

**Technique**: Acknowledge, then redirect
"That's interesting. But I'm curious specifically about..."
"I hear you. Let me ask it differently..."

## When They're Being Promotional

**Technique**: Accept, then pivot to story
"The product sounds great. Take me to the moment you decided to build it."
"Before we get to that—what was the biggest failure on the way there?"

## When They're Uncomfortable

**Technique**: Name it, give an out
"I can tell this is a sensitive topic. We can skip it if you prefer, or..."
"I'm asking because [explain why it matters to listeners]..."

## When You Disagree

**Technique**: Steel-man, then question
"The strongest version of that argument is [X]. But what about [Y]?"

## When They Say Something Wrong

**Technique**: Curious, not confrontational
"That's different from what I've read. Help me understand..."
"Some people would push back on that. What would you say to them?"

Examples

Example 1: Tech Founder Interview Preparation

Context: Interviewing a CEO who recently sold their company for $500M.

Input:

Help me prepare for a podcast interview with Sarah Chen, CEO of DataFlow (just acquired by Microsoft for $500M). Episode theme: the journey from side project to acquisition.

Output:

Interview Preparation: Sarah Chen

Research Summary

• Timeline: Started DataFlow in 2019 as side project, quit Google 2020, Series A 2021, acquisition 2025
• Previous interviews: Forbes, TechCrunch podcast, Bloomberg (all asked standard "founder journey" questions)
• Untapped territory: Her co-founder left in 2022 (never discussed publicly), she's mentioned imposter syndrome on Twitter
• Current focus: Posts about "what comes after" and hints at future projects

Questions That Get Stories

Opening (current, not origin)

1. "You've been pretty quiet since the acquisition was announced. What's been going through your mind these past few weeks?"
2. "I saw you tweeted about 'the silence after the storm.' What did you mean?"

The Journey (inflection points) 3. "Take me to the weekend you decided to quit Google. What was the conversation with your family like?" 4. "I noticed your co-founder David left in 2022, right before the Series B. What happened there?"

• Follow-up: "How did that change how you lead?"

5. "There's a two-month gap in your LinkedIn between leaving Google and officially starting DataFlow. What were those 60 days like?"

The Deal (specifics, not platitudes) 6. "Walk me through the call when Microsoft first reached out. Where were you? What did you think it was about?" 7. "At what point did you decide to sell rather than keep building? What tipped the decision?" 8. "What was the hardest part of the negotiation that no one talks about?"

The Real Stuff 9. "You've mentioned imposter syndrome. At $500M, does it go away?" 10. "What's the conversation with your 2019 self—the one with the side project—look like?" 11. "What did the acquisition cost you that money can't buy back?"

Closing 12. "A year from now, what do you hope to have figured out?" 13. "What question do you wish interviewers would stop asking?"

Follow-Up Triggers

• If she mentions "lucky" → probe for what she actually did
• If she deflects on co-founder → "I understand if you can't share, but listeners are often going through similar..."
• If she mentions family → "How did your [spouse/kids] experience this journey?"

Example 2: Turning Boring Questions Into Gold

Context: Improving standard interview questions for an author interview.

Input:

Review these interview questions and suggest improvements:

1. What's your book about?
2. Why did you write it?
3. What's your writing process?
4. What advice would you give to aspiring writers?

Output:

Question Transformation

Original → Improved

1. "What's your book about?" ❌ Problem: Gets the dust jacket summary

Better:

• "Your book argues [specific thesis]. What's the one story from your research that made you certain you were right?"
• "If someone reads your book and changes ONE thing in their life, what should it be?"
• "What's the most controversial claim in the book, and why are you confident about it?"

2. "Why did you write it?" ❌ Problem: Gets the rehearsed answer

Better:

• "What personal experience made this topic impossible to ignore?"
• "You've been [their job] for 20 years. Why did this particular book demand to be written NOW?"
• "I read that you almost abandoned this project in 2023. What happened?"
• "What were you angry about when you started writing?"

3. "What's your writing process?" ❌ Problem: Gets generic productivity tips

Better:

• "Walk me through the worst writing day you had on this book. What happened and how did you get unstuck?"
• "What's the weirdest ritual that actually helps you write?"
• "Which chapter made you want to quit, and why?"
• "Show me your outline for Chapter 7." (if visual component available)

4. "What advice would you give to aspiring writers?" ❌ Problem: Gets platitudes

Better:

• "What advice do you wish you had ignored?"
• "What's the advice that sounds good but actually doesn't work?"
• "If you could only tell a new writer ONE thing—and it had to be specific and actionable—what is it?"
• "What's a habit you developed that most people would find surprising or uncomfortable?"

Why This Works

Every improved question:

• Asks for a specific story or moment
• Shows you've done your research
• Challenges them to think freshly
• Can't be answered with a rehearsed soundbite

Checklists & Templates

Pre-Interview Checklist

## 48 Hours Before

Research:
- [ ] Read/watched their most significant recent work
- [ ] Listened to 2-3 previous podcast appearances
- [ ] Noted what they're NEVER asked
- [ ] Found one thing that surprised me

Questions:
- [ ] 15-20 questions drafted
- [ ] Questions progress from easy → hard
- [ ] At least 3 questions I'm nervous to ask
- [ ] Follow-up prompts ready for each section

Logistics:
- [ ] Confirmed time (with timezone!)
- [ ] Tested recording setup
- [ ] Backup recording method ready
- [ ] Questions sent to guest (optional, some hosts don't)

Interview Day Checklist

## 30 Minutes Before
- [ ] Tech check complete
- [ ] Recording test confirmed
- [ ] Water bottle ready
- [ ] Questions printed/visible
- [ ] Phone silenced

## During Recording
- [ ] Started with rapport-building
- [ ] Asked permission to go deeper when needed
- [ ] Followed unexpected threads
- [ ] Used silence effectively
- [ ] Listened more than talked

## After Recording
- [ ] Asked "What didn't I ask that I should have?"
- [ ] Captured any off-mic gold
- [ ] Thanked them genuinely
- [ ] Noted key timestamps for editor

Question Bank by Guest Type

## For Founders/Entrepreneurs
- "What was the lowest moment, and how did you get through it?"
- "What's the decision you'd make differently?"
- "What does your inner critic say to you?"

## For Authors/Experts
- "What changed in your thinking while writing this?"
- "What's the critique of your work that stings because it's partially true?"
- "What question do you hope someone asks you?"

## For Executives/Leaders
- "Tell me about a time you were wrong about someone."
- "What's a decision you made that was right but unpopular?"
- "What do you know now that you wish you knew at 30?"

## For Creatives
- "Walk me through the moment you knew this project would work."
- "What did you have to unlearn?"
- "What's the thing you made that you thought would succeed but didn't?"

Skill Boundaries

What This Skill Does Well

• Structuring audio production workflows
• Providing technical guidance
• Creating quality checklists
• Suggesting creative approaches

What This Skill Cannot Do

• Replace audio engineering expertise
• Make subjective creative decisions
• Access or edit audio files directly
• Guarantee commercial success

References

• NPR Training. "NPR's Podcast Start Up Guide" (Glen Weldon) - Professional interview standards
• Tim Ferriss. "The Tim Ferriss Show" (2014-present) - 700+ episodes of interview methodology
• Terry Gross. "Fresh Air" - Master class in creating safe spaces for vulnerability
• Marc Maron. "WTF with Marc Maron" - Authentic conversation technique

Related Skills

• podcast-production - Structuring episodes from interviews
• remote-interview - Technical setup for recording
• voiceover-direction - Directing delivery and performance
• transcription-to-content - Repurposing interview content

Skill Metadata (Internal Use)