Conducting a podcast interview that leads to a great conversation requires a mix of preparation, active listening, curiosity, and adaptability. Here are some key skills and tips for asking questions that spark engaging discussions:

1. Preparation: Know Your Guest and Topic

• Research Your Guest Thoroughly: Understand their background, expertise, recent work, and any personal or professional stories they’ve shared. This allows you to ask specific, meaningful questions that show you’ve done your homework.


• Example: Instead of asking, “Tell me about your career,” say, “I saw that your latest project tackled [specific issue]. What inspired you to dive into that topic?”


• Understand the Audience: Tailor questions to what your listeners care about. Think about what unique insights your guest can provide that align with your podcast’s theme.


• Prepare a Mix of Questions: Have a balance of broad, open-ended questions (to get the conversation flowing) and more specific, detailed questions (to dig deeper into interesting topics).


• Anticipate Follow-Ups: Be ready with follow-up questions based on potential answers. This shows you’re engaged and helps uncover deeper stories.

2. Craft Open-Ended, Thoughtful Questions

• Avoid Yes/No Questions: Questions that can be answered with a simple “yes” or “no” often kill momentum. Instead, frame questions to encourage storytelling or reflection.


• Instead of: “Did you enjoy working on that project?”


• Ask: “What was the most rewarding or challenging part of working on that project?”


• Start with “How” or “What”: These prompts encourage detailed responses.


• Example: “How did you overcome the obstacles you faced early in your career?”


• Example: “What’s one moment in your journey that completely changed your perspective?”


• Focus on Experience and Emotion: Ask questions that tap into personal experiences, feelings, or lessons learned.


• Example: “Can you walk us through a time when you felt completely out of your depth, and how you navigated that?”


• Avoid Overly Complex Questions: Keep questions clear and focused to avoid confusing your guest or derailing the conversation.

3. Be Curious and Build on Responses

• Listen Actively: Great conversations come from genuine interest. Pay close attention to your guest’s answers and ask follow-ups based on what they say, rather than sticking rigidly to a script.


• Example: If they mention a difficult moment, ask, “How did that experience shape the way you approach challenges now?”


• Ask “Why” to Go Deeper: “Why” questions often uncover motivations, values, and unique insights.


• Example: “Why do you think that particular idea resonated so much with your audience?”


• Embrace the Unexpected: If your guest says something surprising or intriguing, don’t be afraid to pivot and explore that topic further, even if it’s off-script.

4. Create a Comfortable Environment

• Build Rapport Early: Start with light, easy questions to help your guest relax. You might chat casually before recording to establish a connection.


• Example: “Before we dive in, I’m curious—how did you get started in this field? Was there a specific moment that sparked your interest?”


• Be Empathetic and Respectful: If discussing sensitive topics, frame questions with care and give your guest space to share as much or as little as they’re comfortable with.


• Example: “I know this might be a tough topic to revisit, but I’d love to hear how you managed to move forward after such a challenging time—if you’re open to sharing.”


• Encourage Storytelling: Phrase questions to invite narratives rather than just facts.


• Example: “Can you take us back to the moment you realized this was your calling? What did that feel like?”

5. Balance Structure with Spontaneity

• Have a Loose Roadmap: While preparation is key, don’t let your list of questions restrict the flow of conversation. Be willing to abandon planned questions if the discussion takes an interesting turn.


• Transition Smoothly: If you’re changing topics, provide context to make the shift feel natural.


• Example: “That’s such a great point about resilience. Speaking of pushing through obstacles, I’d love to hear about your experience with [related topic].”


• Don’t Interrupt: Let your guest finish their thoughts before jumping in with a follow-up or new question. Silence can be powerful—it often gives them space to elaborate.

6. Ask Questions That Spark Unique Insights

• Challenge Assumptions (Gently): Pose questions that invite your guest to think differently or reveal something unexpected.


• Example: “A lot of people assume success in your field comes from [X]. Do you think that’s true, or is there a different factor that’s been more important for you?”


• Ask About Contradictions or Surprises: If something in their story or work stands out as counterintuitive, explore it.


• Example: “I noticed you made a pretty unconventional choice by [X]. What led you to take that path when most people would have done [Y]?”


• Invite Reflection: Questions about lessons learned or personal growth often lead to profound answers.


• Example: “Looking back on everything you’ve accomplished, what’s one thing you wish you’d known earlier?”

7. Engage Your Audience Through Questions

• Ask Relatable Questions: Think about what your listeners might want to ask. Frame questions in a way that feels inclusive.


• Example: “For anyone listening who’s just starting out, what’s one piece of advice you’d give them based on your experience?”


• Encourage Actionable Takeaways: Ask questions that provide value or inspiration for your audience.


• Example: “What’s a simple habit or practice someone could adopt today to improve in [relevant skill or area]?”

8. Handle Difficult Moments Gracefully

• Pivot if a Question Falls Flat: If a guest gives a short or unenthusiastic answer, don’t dwell on it. Move on to another topic with a positive tone.


• Example: “Thanks for sharing that. Let’s shift gears a bit—tell me about [new topic].”


• Address Awkwardness Directly (if Needed): If a question is misunderstood or creates discomfort, acknowledge it and rephrase or move on.


• Example: “I didn’t mean to put you on the spot there—let’s talk about something else. I’m curious about [new topic].”

9. End on a High Note

• Ask a Reflective or Forward-Looking Question: Wrap up with something that leaves the audience inspired or curious.


• Example: “As you look ahead, what’s one thing you’re most excited to tackle next?”


• Example: “If you could go back and tell your younger self one thing, what would it be?”


• Give Them the Floor: Let your guest share anything they’d like to promote or emphasize.


• Example: “Before we wrap up, is there anything you’d love for our listeners to know about or check out?”

10. Practice and Reflect

• Refine Your Skills: After each interview, listen to the recording and note what worked and what didn’t. Were there missed opportunities for follow-ups? Did certain questions spark great responses?


• Seek Feedback: Ask trusted listeners or peers for input on your interviewing style and question choices.


• Experiment: Try different types of questions (personal, professional, hypothetical) to see what resonates most with your guests and audience.

By combining preparation, genuine curiosity, and active listening, you can ask questions that not only engage your guest but also captivate your audience. Great conversations often come from creating a space where your guest feels valued and excited to share their story. Keep practicing, and over time, you’ll develop a natural flow that makes every interview memorable!

Of course! This is a fantastic goal. Moving from a standard Q&A to a truly great conversation is what separates good podcasts from unforgettable ones. It's about being a guide, not an interrogator.

Here’s a comprehensive guide to asking questions that create great conversations, broken down into mindset, preparation, and specific question types.

The Foundation: The Interviewer's Mindset

Before you even write a question, adopt this mindset:

• Be a Curious Listener, Not a Talk Show Host: Your primary job is to draw out the guest. Your ego is secondary. Listen actively to their answers, and be prepared to follow the thread, even if it leads away from your script.


• Serve the Audience: You are the audience's proxy. You're asking the questions they would ask if they were in the room. Your goal is to make the guest look good, sound interesting, and share their most valuable insights.


• Embrace the "Conversation," Not the "Interrogation": Think of it as a collaborative exploration of a topic. Your guest is your partner in creating something interesting for the listeners.

Phase 1: Deep Preparation (The Work Before the Mic)

Great questions are born from great preparation.

• Research Extensively: Go beyond their Wikipedia page.


• Listen to their other recent interviews to avoid the same old questions.


• Read their book, watch their TED Talk, use their product.


• Look for their recent social media posts. What are they thinking about right now?


• Find the "Gold": As you research, note down:


• Contradictions: "In 2018, you said X, but now you're doing Y. What changed your mind?"


• Personal Turning Points: "What was the moment you knew you had to leave your stable job and start this company?"


• The "Why" Behind the "What": Everyone knows what they did. The great conversation is about why they did it and how it felt.


• Create a "Road Map," Not a Script: Have a list of topics and key questions, but be flexible. Number them so you can jump around easily if the conversation flows.

Phase 2: The Toolkit of Great Questions

Here are specific types of questions to have in your toolkit, moving from openers to deep dives.

1. The Icebreakers & Openers (Setting the Tone)

Goal: Make the guest comfortable and signal that this will be different.

• Instead of: "Tell me about yourself."


• Try:


• "What's a project or idea that has you most excited right now?" (Forces a present-tense, passionate answer).


• "For our listeners who might not know your work, if you had to describe the central theme of what you do, what would it be?" (More philosophical and engaging).


• "Let's start at a turning point. What was the catalyst for [their famous project/company]?"

2. The "Story" Questions (Creating Narrative)

Goal: Humans are wired for stories. Unearth them.

• The "Origin Story": "Take us back to the very beginning. Where were you and what were you feeling when the idea for [X] first hit you?"


• The "Struggle" Question: "What was the lowest point, the moment you almost gave up? What did that feel like, and what got you through it?" (This creates huge empathy).


• The "Aha! Moment": "Was there a specific conversation, failure, or piece of data that suddenly made everything click?"

3. The "Peeling the Onion" Questions (Going Deeper)

Goal: Avoid surface-level answers. Use follow-ups to dig deeper.

• The Simple "Why?": After any declarative statement, a gentle "Why?" or "What makes you say that?" is incredibly powerful.


• The "How Did That Feel?": Facts are forgettable; emotions are memorable. "You achieved this huge milestone. What did that success feel like after all the struggle?"


• Ask for Specifics: "That's fascinating. Can you give me a specific example of what that looked like in practice?"

4. The "Challenging but Respectful" Questions

Goal: Create tension and credibility without being confrontational.

• The "Devil's Advocate": "Some people in your industry argue [opposing viewpoint]. How do you respond to that criticism?"


• The "Reframing" Question: "It seems like the common wisdom about this is X, but your work suggests Y. How did you arrive at such a different conclusion?"


• Addressing Failure: "Let's talk about [a known failure or setback]. What did you learn from that experience that you couldn't have learned any other way?" (Frames failure as a lesson).

5. The "Forward-Looking" & "Big Picture" Questions

Goal: End on a high note and leave the audience with something to think about.

• The "Future Casting": "Based on what you're working on now, what do you see changing in our world in the next 5-10 years?"


• The "Legacy" Question: "When people look back on your life's work, what is the one thing you hope they'll remember or that it led to?"


• The "Action" Question: "If our listeners take away one thing from our conversation today and want to act on it, what should that be?"

Phase 3: The Art of the Follow-Up & Active Listening

This is where the magic happens during the interview.

• Let There Be Silence: Don't rush to fill a pause after an answer. A moment of silence often prompts the guest to elaborate with their most profound thought.


• Abandon Your Script: If the guest says something fascinating that's not on your list, follow it! Say, "That's so interesting, I have to ask you more about that." This makes the conversation authentic.


• Paraphrase for Clarity: "So, if I'm understanding you correctly, you're saying that the key wasn't the idea itself, but the timing?" This shows you're listening and helps the audience follow along.


• Connect the Dots: "What you just said about your childhood really reminds me of what you mentioned earlier about your leadership style. Are those two connected?"

Quick-Fire List: Questions to Avoid

• The Yes/No Question: "Was that difficult?" (Instead, ask "In what ways was that difficult?")


• The Multi-Part Question: "What was your strategy, how did you fund it, and what would you do differently?" (They'll only answer one. Ask them separately.)


• The Leading Question: "That must have been incredibly exciting, right?" (It puts words in their mouth. Let them describe it.)


• The Vague, Clichéd Question: "What's your secret to success?"

Final Pro-Tips

• Pre-Interview Chat: Have a 5-10 minute informal chat before you hit record. This builds rapport and calms nerves.


• End Strong: Always end by asking the guest how people can find them and their work. And thank them sincerely for their time and insights.

Podcast Interview Skills: Crafting Questions for Great Conversations

The Foundation: Mindset Shift

Think conversation, not interrogation. The best podcast interviews feel like you're eavesdropping on a fascinating chat between friends, not witnessing a formal Q&A session.

Types of Questions That Spark Great Conversations

1. Open-Ended Story Starters

• "Tell me about a time when..."


• "Walk me through what happened when..."


• "What was going through your mind during...?"


• "Paint me a picture of..."

2. Emotional Gateway Questions

• "How did that feel?"


• "What surprised you most about...?"


• "What would you tell your younger self about...?"


• "What keeps you up at night?"

3. Contrarian/Challenge Questions (Use Carefully)

• "Some people might argue that... How would you respond?"


• "Playing devil's advocate here..."


• "What would critics say about your approach?"

4. Behind-the-Scenes Questions

• "What don't people understand about...?"


• "What happens behind closed doors that people don't see?"


• "What's the unsexy part of your work that nobody talks about?"

Advanced Conversation Techniques

The Follow-Up Ladder

• Initial question


• "Tell me more about that..."


• "What did that teach you?"


• "How has that changed your approach to...?"

The Assumption Flip

The Vulnerability Bridge

Question Preparation Strategies

Research-Based Questions

• Surface level: Basic facts anyone could Google


• Deep level: Insights only they can provide based on their unique experience

The 70-30 Rule

• 70% prepared questions


• 30% space for spontaneous follow-ups

Question Categories to Prepare

• Origin story: How they got started


• Turning points: Key moments that changed everything


• Current work: What they're focused on now


• Lessons learned: Wisdom they've gained


• Future vision: Where they're headed

Conversation Flow Management

Smooth Transitions

• "That reminds me of something..."


• "Speaking of [topic they just mentioned]..."


• "You touched on something interesting there..."

When to Interrupt (Politely)

• Guest goes off on a tangent: "That's fascinating. Before we lose this thread, can you tell me more about...?"


• Guest gives a surface answer: "Can you dive deeper into that?"

Creating Contrast

Common Mistakes to Avoid

The Machine Gun Approach

The Leading Witness

The Wikipedia Trap

The Ego Interview

Creating Memorable Moments

The Hypothetical Scenario

The Desert Island Question

The Crystal Ball

Handling Difficult Situations

When Guests Give Short Answers

• "Can you expand on that?"


• "What's an example of that?"


• "Help me understand what you mean by..."

When Conversation Stalls

• "What's the most common misconception people have about your work?"


• "What question do you wish people would ask you but they never do?"

When Guests Get Defensive

• Acknowledge their perspective first


• Reframe as curiosity, not challenge


• "I'm asking because our audience would be curious about..."

The Art of Active Listening

Listen for:

• **Emotional