Best Podcast Interview Questions: How to Conduct Engaging Guest Conversations in 2021

📅 Updated March 2026 | ⏱️ 14 min read | 🏷️ Interview Skills
The 3 Pillars
Great Interviews = Deep Preparation + Genuine Curiosity + Active Listening

Some of the most downloaded podcast episodes are interviews. Not because the host got lucky — but because they knew how to draw out compelling stories, ask follow-up questions that nobody else asks, and create a conversation that listeners can't stop listening to.

Whether you're launching your first interview show or you're a seasoned host looking to level up, this guide covers everything: how to prepare, which questions to ask, how to handle awkward silences, and how to end interviews on a high note.

Before You Ask Any Question: Preparation Framework

The difference between a mediocre interview and a memorable one often happens before you hit record. Proper preparation signals respect for your guest and allows you to ask questions that go beyond surface-level content.

✅ Pre-Interview Checklist

  • Listen to at least one previous interview the guest has done
  • Read 3-5 of their articles, posts, or press mentions
  • Identify 2-3 specific things they said that you want to explore
  • Prepare a tailored intro that references their specific work
  • Send guest 3-5 top-level questions 24 hours in advance (optional but appreciated)
  • Test all recording equipment and internet connection
  • Set up a comfortable, quiet recording space

The 75+ Best Podcast Interview Questions by Category

Opening / Icebreaker Questions

The first few minutes set the tone. Use these to put guests at ease and establish rapport:

Opening

"I was listening to your interview on [Podcast Name] last year, and you mentioned [specific thing]. Has your thinking on that changed since then?"

Opening

"What's something about your field that most people in it won't admit or talk about openly?"

Opening

"If I asked your team to describe you in three words, what would they say?"

Opening

"What was the moment you realized this — whatever 'this' is for you — was actually going to be your path?"

Origin Story Questions

Everyone has a story about how they got to where they are. These questions dig into the journey:

Origin

"What were you doing before you got into [their current field]? And what triggered the pivot?"

Origin

"Who or what was your biggest influence when you were first starting out?"

Origin

"What's a failure or setback that you now consider one of your greatest teachers?"

Origin

"What did your first year look like? What surprised you most about the reality of this work?"

Insight & Expertise Questions

These dig into the meat of what your guest actually knows:

Expertise

"What's a commonly held belief in your industry that you strongly disagree with?"

Expertise

"What's the biggest misconception beginners in your field have that you wish you could correct on day one?"

Expertise

"What skill or habit has had the biggest positive impact on your results that most people overlook?"

Expertise

"If you could go back and give yourself advice on your first day in this field, what would it be?"

Story-Telling Questions

The best podcast episodes are driven by stories. Use these to get guests to share vivid, specific narratives:

Stories

"Tell me about a specific moment — a real, specific moment — when things really shifted for you."

Stories

"What's the hardest conversation you've ever had to have in your career, and what came from it?"

Stories

"What's a mistake you see people in your position make over and over that you made yourself once?"

Contrarian / Bold Questions

These push guests out of their comfort zone and often produce the most shareable moments:

Bold

"What's something you believe about success or wealth that most people would disagree with?"

Bold

"What do you think is overrated in your industry right now?"

Bold

"If your industry had a reset button, what would you eliminate or change completely?"

Personal / Philosophical Questions

These reveal the human behind the professional brand:

Personal

"What does a typical day look like for you, and has that changed over the years?"

Personal

"What do you do when you're stuck — when inspiration isn't coming and you have to produce anyway?"

Personal

"What are you most proud of that nobody knows about or that doesn't get talked about?"

Forward-Looking Questions

Future

"What's next for you — and what excites or scares you most about it?"

Future

"What trend in your industry are you most paying attention to right now?"

Future

"If you were starting from zero today, knowing what you know, what's the first thing you'd do?"

How to Ask Follow-Up Questions That Actually Work

The single most important interviewing skill is the follow-up. Most hosts ask a question, get an answer, then move on. The best interviewers stay on a thread until they've extracted everything valuable.

The LAER Method: Listen, Acknowledge, Explore, Respond

After your guest finishes an answer, briefly acknowledge what they said, then ask a follow-up that goes deeper before moving to your next prepared question.

Weak Follow-Up Strong Follow-Up
"That's interesting. OK, next question...""You said you almost gave up. What was the specific moment that almost broke you?"
"So you learned X. Any final thoughts?""Walk me through what it actually felt like to implement X for the first time — what surprised you?"
"Thanks for sharing that. Let's move on.""You mentioned your co-founder pushed back on that decision. What specifically did they say?"

Handling Difficult Interview Situations

The Guest Who Gives Short Answers

Some guests are naturally reserved. Instead of asking more questions, try:

The Guest Who Goes Off Track

If a guest rambles or goes on tangents:

The Guest Who Is Clearly Nervous

Start with lighter, fun questions before going deep. Mirror their energy — if they're formal, be more structured; if they're casual, be conversational. Tell them early: "There are no wrong answers here. I'm genuinely curious about your experience."

How to End an Interview Strongly

The ending shapes how listeners remember the episode. A weak ending ( "That's all I have, thanks for coming on!") wastes an opportunity.

💡 The Perfect Ending Formula

End with the Lightning Round (rapid-fire personal questions) or the Legacy Question: "If this was your last podcast interview ever, what would you most want people to remember or take away?"

Also always ask: "Where can people find you / follow you / learn more?" This drives listeners to take action after listening.

Questions to Always Ask (The "Cheat Sheet" List)

Keep these in your back pocket for every interview:

  1. What's the most important thing you'd want someone to understand about what you do?
  2. Who should I be following or reading that's doing interesting work right now?
  3. What's a tool, book, or resource that's changed how you work?
  4. If our listeners remember one thing from today, what should it be?
  5. What's next for you, and how can people stay in touch?

Final Thoughts

Great podcast interviewing is a skill that improves with every conversation. The hosts you admire most — Joe Rogan, Tim Ferriss, Lex Fridman — didn't become great by accident. They prepared thoroughly, listened actively, and followed interesting threads wherever they led.

Start with this guide, pick 10 questions that resonate with you, and use them in your next interview. You'll be amazed at how quickly your episodes improve.