10 Best ChatGPT Prompts for Podcast Interviews (2024)

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The Science Behind Effective Podcast Interview Questions

Great podcast interviews don’t happen by accident. They’re the result of smart preparation, deep listening, and questions that make guests want to share their best stories. But here’s the thing: most podcasters ask the same tired questions—“How did you get started?” or “What’s your biggest challenge?”—and wonder why their episodes feel flat. The difference between a forgettable interview and one that listeners rave about? Personalization.

Research shows that tailored questions boost engagement by up to 40%. Why? Because people don’t just want to hear answers—they want to feel something. A generic question gets a generic response. But a question that digs into a guest’s unique experiences? That’s where the magic happens. Think about the last time you heard a podcast where the host seemed to really know their guest. It probably made you lean in, right? That’s the power of personalization at work.

Why Your Brain Loves a Good Story

Great interview questions tap into psychological triggers that make responses memorable. Three big ones:

Curiosity – Questions that make the guest (and listener) think, “Wait, how did that happen?” Example: “You mentioned on LinkedIn that you failed at your first startup. What’s one thing no one tells you about failure?”
Vulnerability – People connect with authenticity. A question like “What’s a fear you had to overcome to get where you are?” invites deeper reflection than “What’s your success story?”
Storytelling – The brain remembers stories 22x more than facts. Instead of “What do you do?” try “Tell me about a time when your work changed someone’s life.”

Here’s a pro tip: Use the peak-end rule. This psychology principle says people remember the most intense moment and the end of an experience. Structure your questions so the best stories come at the climax of your interview, and end with a question that leaves listeners thinking. Example: “If you could go back and tell your younger self one thing about this journey, what would it be?”

How to Read a LinkedIn Profile Like a Detective

Most podcasters skim a guest’s LinkedIn and call it research. Big mistake. A LinkedIn profile is a goldmine if you know where to look. Here’s what to focus on:

Experience section – Don’t just note job titles. Look for gaps, career pivots, or unusual roles. Example: If a guest went from teaching to tech, ask “What’s one skill from teaching that surprised you in your tech career?”
Posts and articles – What are they passionate about? A guest who writes about mental health at work? Ask “You’ve talked a lot about burnout. What’s one small change leaders can make to help their teams?”
Recommendations – These reveal how others see them. If a colleague calls them “the most resilient person I know,” dig into that: “What’s a time resilience was tested in your career?”
Skills – Not just what they list, but what’s missing. If someone’s a CEO but doesn’t list “public speaking,” ask “What’s a skill you’ve had to learn on the job that surprised you?”

The biggest mistake? Assuming you know what their achievements mean. Example: If a guest says they “scaled a team from 5 to 50,” don’t just say “Wow, that’s impressive!” Ask “What’s one thing you’d do differently if you scaled a team again?” That’s how you get the real story.

The Questions Most Podcasters Get Wrong

Here’s what separates the amateurs from the pros:

❌ Surface-level questions – “What’s your morning routine?” (Boring. Everyone asks this.) ✅ Deeper version – “What’s one habit you thought would help your career but actually held you back?”

❌ Overused “advice” questions – “What’s your best advice for aspiring entrepreneurs?” (Too vague.) ✅ Specific version – “What’s a piece of advice you ignored early on that you wish you’d listened to?”

❌ Ignoring recent content – If a guest just posted about a big project, don’t ask “What’s new with you?” Ask “I saw you just launched [X]. What’s one thing that surprised you during the process?”

The key? Listen more than you talk. The best interviewers don’t just ask questions—they follow the thread. If a guest mentions a struggle, dig deeper. If they share a win, ask “What did it take to get there?” That’s how you turn a good interview into a great one.

10 ChatGPT Prompts to Craft Unique Podcast Questions

Great podcast interviews feel like conversations, not interrogations. The best questions make guests think, laugh, or even pause before answering. But how do you avoid the same old “What inspired you?” or “How did you get started?” questions? The secret is in the details—specifically, your guest’s LinkedIn profile.

Most interviewers skim a guest’s bio and call it a day. But if you dig deeper, you’ll find gold. A career pivot here, a bold opinion there, or even a project that didn’t go as planned. These are the moments that turn a good interview into a great one. Below are 10 ChatGPT prompts to help you craft questions that surprise, engage, and uncover stories your audience won’t hear anywhere else.

1. The “Career Pivot” Question

People love stories of change. A career pivot isn’t just about switching jobs—it’s about unlearning old beliefs and embracing new ones. Instead of asking, “Why did you leave your old job?” try something like:

“I noticed you shifted from [X industry] to [Y]. What’s one belief you held before that changed after this move?”

This question works because it forces the guest to reflect. Maybe they thought corporate life was the only path to success—until they tried freelancing. Or perhaps they assumed leadership was about control, only to learn it’s about trust. These answers reveal growth, and that’s what listeners connect with.

Pro tip: Look for gaps or unusual transitions in their experience section. Did they take a year off? Switch from a technical role to a creative one? Those are your hooks.

2. The “Controversial Take” Question

LinkedIn is full of bold opinions. Your guest has probably posted something that sparked debate—maybe about remote work, AI, or company culture. Instead of ignoring it, lean in. Ask:

“In your recent post about [topic], you mentioned [controversial point]. What’s the strongest pushback you’ve received?”

This does two things:

It shows you’ve done your homework.
It turns a one-sided opinion into a real conversation.

Guests love when interviewers engage with their ideas. And if they’ve faced criticism, they’ll have stories to share—stories that make your podcast stand out.

3. The “Behind-the-Scenes” Question

Most bios list achievements, but they don’t tell the full story. What went wrong? What was the messy middle? Dig into a specific project or role with:

“Your LinkedIn shows you led [project]. What’s one thing that went wrong—and how did you fix it?”

This question works because it’s human. No one succeeds without failures, and listeners want to hear about the struggles, not just the wins. Plus, it gives your guest permission to be vulnerable—which makes for a more engaging interview.

Example: If your guest led a product launch, ask about the last-minute bug that almost derailed everything. How did they handle it? What did they learn?

4. The “Industry Trend” Question

Skills and endorsements on LinkedIn aren’t just for show—they’re clues about where the industry is headed. Instead of asking, “What’s the future of [industry]?” (yawn), try:

“You’re highly endorsed for [skill]. How do you see this evolving in the next 5 years?”

This question works because it’s specific. If your guest is a data scientist, ask about the future of AI tools. If they’re a marketer, ask about the shift to short-form video. Their answer will give listeners actionable insights—and position your guest as a thought leader.

5. The “Personal Growth” Question

Recommendations on LinkedIn are like mini-testimonials. They reveal how others see your guest. Use them to ask about mentorship, learning, or even unlearning:

“[Colleague] mentioned you’re great at [skill]. What’s one thing you’ve had to unlearn to master it?”

This question is powerful because it flips the script. Instead of asking, “How did you get good at this?” you’re asking, “What did you have to let go of?” That’s where the real growth happens.

Example: If someone says your guest is a great public speaker, ask what bad habits they had to break to get there. Did they used to overprepare? Did they fear silence? These answers are gold.

6. The “Audience-Specific” Question

Your listeners are your secret weapon. Instead of asking generic questions, tailor them to your audience. Try:

“If [ideal listener] were here, what’s one misconception about [topic] you’d want to clear up?”

This question works because it makes the guest think about your audience, not just themselves. It also positions your podcast as a place where real problems get solved.

Example: If your podcast is for entrepreneurs, ask, “What’s one thing most founders get wrong about fundraising?” If it’s for creatives, ask, “What’s a myth about making money from art that you wish would die?”

The Rest of the Prompts (And Why They Work)

The remaining prompts follow the same principle: dig deeper, ask smarter, and make it personal. Here’s a quick rundown:

The “Failure-to-Success” Question: “Your early career shows [challenge]. How did that shape your approach to [current role]?” (Highlights resilience.)
The “Hot Take” Question: “You recently commented on [trend]. What’s one thing most people get wrong about it?” (Sparks debate.)
The “Future Vision” Question: “Your profile suggests you’re passionate about [cause]. What’s one change you’d like to see in the next decade?” (Shows long-term thinking.)
The “Wildcard” Question: “If you could have a 10-minute conversation with [historical figure] about [topic], what would you ask?” (Surprises and delights.)

How to Use These Prompts with ChatGPT

You don’t need to memorize these questions—just feed them into ChatGPT with a few details about your guest. For example:

“My guest is a former teacher who now works in tech. They recently posted about the challenges of remote work. Give me 3 unique interview questions based on their LinkedIn profile.”

ChatGPT will generate questions like:

“What’s one classroom skill that surprised you in your tech career?”
“You’ve talked about remote work challenges. What’s one thing companies still don’t get about it?”
“If you could go back and tell your teaching self one thing about tech, what would it be?”

Pro tip: Always tweak the questions to fit your guest’s tone. If they’re funny, make the question playful. If they’re serious, keep it thoughtful.

The Secret to a Great Interview

The best interviews don’t feel like interviews—they feel like conversations. And the best questions don’t just scratch the surface; they dig into the why behind the story.

So next time you’re prepping for a guest, don’t just skim their bio. Look for the pivots, the controversies, the failures, and the passions. Those are the moments that make your podcast unforgettable.

How to Use These Prompts Effectively

You found the perfect guest for your podcast. They have an interesting story, great experience, and your audience will love them. But now comes the hard part: what do you ask them? Generic questions like “Tell us about yourself” won’t cut it. You need questions that make your guest think, share real insights, and keep listeners hooked.

That’s where these ChatGPT prompts come in. But here’s the thing: AI is just a tool. It won’t do the work for you. You still need to put in the effort to make the interview feel human, engaging, and unique. Here’s how to use these prompts the right way—so your podcast stands out.

Step 1: Scrape LinkedIn for Key Insights (Without Being Creepy)

Before you even open ChatGPT, you need to know your guest inside out. LinkedIn is your best friend here. But don’t just skim their profile—dig deeper.

Look at their experience section. What jobs did they have? Did they switch careers? Example: If your guest went from being a teacher to a tech CEO, ask: “What’s one lesson from teaching that helped you in tech?”
Check their posts and articles. What do they care about? If they write about mental health at work, ask: “You’ve talked about burnout a lot. What’s one small change companies can make to help employees?”
Read their recommendations. How do others describe them? If someone calls them “the most resilient person I know,” ask: “What’s a time your resilience was really tested?”
Notice what’s missing. If they’re a CEO but don’t list “public speaking” as a skill, ask: “What’s a skill you had to learn on the job that surprised you?”

The goal isn’t to stalk your guest—it’s to find the interesting parts of their story. The parts that make them human, not just another expert.

Step 2: Feed ChatGPT the Right Context (Or It’ll Give You Generic Questions)

Now that you have insights, it’s time to use ChatGPT. But here’s the mistake most people make: they give it too little information. If you just say “Give me podcast questions for a marketing expert,” you’ll get boring, generic questions.

Instead, give ChatGPT context. Here’s how to structure your prompt:

“My podcast guest is [Name]. Here’s their LinkedIn bio: [paste bio]. They’ve worked at [Company A] and [Company B], and they often write about [Topic]. Their last post was about [Subject]. Based on this, give me 10 unique podcast questions that will make them share real stories and insights. Avoid generic questions like ‘Tell us about yourself.’”

The more details you give, the better the questions will be. If your guest has a funny story in their bio (like “I once accidentally emailed the whole company a cat meme”), mention it. ChatGPT might suggest: “You once emailed the whole company a cat meme. What’s the funniest work mistake you’ve made?”

Step 3: Refine the Output (Because AI Still Sounds Like a Robot)

ChatGPT is smart, but it’s not perfect. The questions it gives you might be close, but they won’t always sound natural. Your job is to tweak them so they feel like a real conversation.

Here’s how to fix AI-generated questions:

Make them shorter. AI loves long, wordy questions. Cut them down. Instead of: “Can you share with us a pivotal moment in your career where you faced a significant challenge and how you overcame it?” Try: “What’s a time you failed at work? How did you bounce back?”
Add personality. If your podcast is casual, make the questions sound like you. Instead of: “What advice would you give to aspiring entrepreneurs?” Try: “If you could go back and tell your younger self one thing, what would it be?”
Ask follow-ups. AI gives you the first question, but the best interviews happen when you dig deeper. If your guest says, “I quit my job to start a business,” don’t just move on. Ask: “What was the hardest part about that decision?”

Step 4: Sequence Questions for Flow (Or Your Interview Will Feel Like a Checklist)

A great interview has a natural flow. It starts light, builds momentum, and ends with a strong takeaway. If you ask random questions, your guest (and audience) will feel lost.

Here’s how to order your questions:

Start with an easy, fun question. Example: “What’s something most people don’t know about you?” This helps your guest relax.
Move to their expertise. Example: “You’ve worked in [Industry] for 10 years. What’s changed the most?”
Dig into challenges. Example: “What’s a time you failed? What did you learn?”
End with actionable advice. Example: “If someone wants to do what you do, what’s the first step they should take?”

Think of it like a story. You want a beginning, middle, and end. If your questions jump around, your interview will feel disjointed.

Step 5: Don’t Rely Too Much on AI (Or Your Interview Will Feel Fake)

Here’s the truth: AI is a great starting point, but it’s not the finish line. If you only use ChatGPT’s questions, your interview will sound robotic. The best podcasts feel like real conversations, not scripted Q&As.

Here’s when to deviate from AI:

If your guest says something unexpected. AI can’t predict what your guest will say. If they mention a struggle, ask: “What was going through your mind at that moment?”
If the conversation takes a turn. Maybe your guest brings up a topic you didn’t plan for. Go with it! Some of the best moments happen when you improvise.
If the question feels too formal. If ChatGPT suggests “What are your thoughts on the future of AI?” but your podcast is casual, rephrase it: “Okay, real talk—are robots going to take our jobs?”

The best interviews happen when you listen more than you talk. AI can give you questions, but it can’t replace your curiosity.

Final Tip: Practice Makes Perfect

The first time you use these prompts, it might feel awkward. That’s okay! The more you practice, the better you’ll get at:

Finding the real stories in a LinkedIn profile.
Tweaking AI questions to sound natural.
Letting the conversation flow instead of sticking to a script.

So go ahead—try these prompts with your next guest. See what works, what doesn’t, and adjust. Your audience (and your guests) will thank you.

Case Studies: Podcasters Who Nail Personalized Questions

Great podcast interviews don’t happen by accident. The best hosts spend hours researching their guests—not just skimming their bio, but digging into their LinkedIn posts, past interviews, and even the way they describe their own work. Here’s how three podcasters turned that research into unforgettable conversations.

Case Study 1: “The Growth Mindset Podcast” – The Question That Went Viral

When host Sarah Chen interviewed startup founder Mark Rivera, she didn’t ask the usual “How did you start your company?” Instead, she noticed a small detail in his LinkedIn profile: a year-long gap where he traveled solo across Asia. She asked:

“You took a year off to travel before building your company. What’s one fear you had to overcome during that time—and how did it shape your leadership style?”

The answer? A raw, 10-minute story about failure, resilience, and how traveling alone taught him to trust his instincts. Listeners loved it—shares of that episode jumped 200%, and Mark later said it was the most personal interview he’d ever done.

Key takeaway: The best questions come from specific details. Don’t just ask about their career—ask about the moments that changed them.

Case Study 2: “Behind the Hustle” – Turning a LinkedIn Post Into a Standout Moment

Host Jamal Carter is known for his “research-first” approach. Before interviewing marketing expert Priya Kapoor, he noticed a LinkedIn post where she wrote:

“I once spent $50,000 on a campaign that failed. Here’s what I learned.”

Instead of asking about her successes, Jamal dug into that failure:

“You’ve talked about a $50K campaign that didn’t work. What’s one thing you wish you’d known before hitting ‘launch’?”

Priya’s answer—about the importance of testing small before scaling—became the most quoted part of the episode. Even better? The post she referenced got 500+ new comments after the interview.

Key takeaway: Guests often bury their best stories in LinkedIn posts. Find them, and ask about them.

Case Study 3: “The Creative Edge” – Balancing AI Prompts with Human Follow-Ups

Some hosts worry that using AI prompts will make interviews feel robotic. But host Elena Torres proves you can use AI and keep things natural. Her secret? The 80/20 rule:

80% AI-assisted: She starts with ChatGPT prompts based on her guest’s LinkedIn (e.g., “Ask about their biggest career pivot”).
20% human-led: She listens closely and follows up on unexpected answers.

For example, when interviewing designer Alex Chen, she used an AI prompt to ask about his design process. But when he mentioned “I sketch ideas on napkins,” she dropped the script and asked:

“What’s the weirdest place you’ve ever sketched a design?”

His answer—a napkin from a plane ride that later became a million-dollar product—became the highlight of the episode.

Key takeaway: AI can help you prepare, but the best moments happen when you listen and go off-script.

What These Podcasters Have in Common

These hosts don’t just ask questions—they craft them. Here’s how you can do the same:

Look for the “hidden stories” (gaps in resumes, old posts, recommendations).
Ask about failures, not just successes—people remember honesty.
Use AI as a starting point, not the final script.
Follow the thread—if a guest mentions something interesting, dig deeper.

The best interviews feel like conversations, not Q&As. And the best questions? They come from real curiosity—not a generic list. So next time you prep for a guest, ask yourself: What’s the one thing no one else has asked them? That’s where the magic happens.

Advanced Tactics: Taking Your Interview Questions to the Next Level

You’ve got the basics down—you know how to research your guest’s LinkedIn profile and ask questions that go beyond the usual “tell us about your journey.” But how do you make your interview stand out? How do you dig deeper, keep the conversation flowing, and leave your listeners wanting more? That’s where these advanced tactics come in.

The “5 Whys” Technique: Digging Deeper Without Sounding Like a Detective

You’ve probably heard of the “5 Whys” technique—it’s a simple but powerful way to get to the root of any story. The idea is to keep asking “why” until you uncover the real emotion or lesson behind what your guest is saying. But here’s the trick: you don’t have to ask “why” five times in a row. Instead, use it as a guide to layer your questions naturally.

For example, if your guest says, “I left my corporate job to start my own business,” don’t just move on. Ask:

“What was the moment you realized you needed to leave?” (Why?)
“How did your family react when you told them?” (Why did that matter?)
“What’s one thing you miss about your old job?” (Why does that surprise you?)

This way, you’re not interrogating your guest—you’re helping them share a richer story. And your listeners will thank you for it.

Blending Listener Questions with LinkedIn Insights

Your audience is full of curious people who want to know more about your guest. Why not let them help shape the interview? Before the episode, ask your followers on social media: “What would you ask [Guest Name] if you had the chance?” Then, weave their questions into your conversation.

But don’t just read the questions verbatim—use them as a starting point. For example, if a listener asks, “What’s your biggest failure?” you could reframe it like this: “One of our listeners wants to know about your biggest failure. But I’m curious—what’s a failure you didn’t see coming?”

This keeps the conversation fresh and makes your audience feel like they’re part of the show.

Using ChatGPT for Dynamic Follow-Up Questions

ChatGPT isn’t just for generating your initial questions—it can also help you think on your feet. If your guest says something unexpected, you can quickly ask ChatGPT for follow-up ideas. For example, if your guest mentions a challenge they faced, you could prompt ChatGPT with: “My guest just said they struggled with [topic]. Give me 3 follow-up questions to dig deeper.”

This way, you’re not stuck scrambling for the next question. You’re keeping the conversation flowing naturally.

Avoiding “Interrogation Mode”

No one likes feeling like they’re being grilled. The best interviews feel like a conversation, not a Q&A session. How do you keep it natural? Here are a few tips:

Listen more than you talk. If your guest says something interesting, don’t rush to the next question. Let them expand.
Share your own thoughts. If your guest mentions a challenge, you could say, “I’ve been there too—how did you push through?”
Use silence. Sometimes, the best follow-up is just waiting a beat. Your guest might fill the silence with something even more interesting.

Measuring What Works (And What Doesn’t)

Not every question will land. That’s okay! The key is to learn from each interview. Here’s how to track what works:

Listener retention. Do people drop off after a certain question? Maybe it’s too generic.
Social shares. Which parts of the interview get the most shares? Those are the moments people love.
Guest feedback. After the interview, ask your guest: “What was your favorite question?” Their answer might surprise you.

The best interviewers aren’t afraid to experiment. Try new questions, see what resonates, and refine your approach over time. Your audience—and your guests—will notice the difference.

Common Pitfalls and How to Avoid Them

Podcast interviews can feel like walking a tightrope. Too much preparation, and the conversation feels stiff. Too little, and you’re left scrambling for questions. The best interviews sound natural, but getting there takes practice—and avoiding some common mistakes.

Let’s talk about the biggest pitfalls and how to fix them.

Over-Researching Kills Spontaneity

You’ve spent hours reading your guest’s LinkedIn, blog posts, and past interviews. You know their favorite book, their first job, and their thoughts on industry trends. But when the mic turns on, the conversation feels… robotic.

Here’s the problem: over-preparing can make you sound like a checklist. You ask about their career, their book, their big achievement—and then what? The magic happens when you listen and follow up on their answers.

How to fix it:

Pick 3-5 key points from their background (not 20).
Focus on stories, not facts. Instead of “You worked at Google—what was that like?” try “What’s one thing no one tells you about working at Google?”
Leave room for surprises. If they mention a hobby or side project, ask about it—even if it wasn’t in your notes.

Leading Questions Sound Fake

“Don’t you think remote work is the future?” “You must agree that AI is changing everything, right?”

These questions don’t start conversations—they end them. Your guest will either agree (boring) or feel pressured to say something they don’t believe (awkward).

Better approach:

Ask open-ended questions: “How do you see remote work evolving in the next five years?”
Let them share their real opinion: “What’s one thing people get wrong about AI?”

Ignoring Your Guest’s Communication Style

Some guests love to talk. Others need a little coaxing. If you ask a chatty extrovert “Tell me about your career”—they’ll take 20 minutes. But if you ask the same question to an introvert, you might get a one-word answer.

How to adapt:

For extroverts: Ask specific, narrow questions. “What was the hardest part of launching your startup?”
For introverts: Give them time to think. “Take a second—what’s one lesson you wish you’d learned earlier?”
Watch their body language. If they light up when talking about a topic, dig deeper.

Failing to Listen Actively

You’ve got your list of questions. You ask the first one, they answer, and you move to the next—without really hearing what they said.

This is the biggest mistake interviewers make. The best questions come from listening, not from your notes.

Example: Guest: “I actually failed my first startup. It was a disaster.” Bad follow-up: “So, what’s your advice for entrepreneurs?” Good follow-up: “What was the moment you realized it wasn’t working?”

Pro tip: If a guest says something interesting, pause. Let the silence sit for a second. Often, they’ll keep talking—and share something even better.

When AI Suggestions Go Wrong

ChatGPT can give you great question ideas, but it’s not perfect. Sometimes, its suggestions sound generic or don’t fit your guest’s personality.

How to use AI the right way:

Use it for inspiration, not a script.
If a question feels off, rewrite it in your own words.
Add personality. Instead of “What’s your biggest challenge?” try “What’s the one problem that keeps you up at night?”

Final thought: The best interviews feel like conversations, not Q&As. Avoid these pitfalls, and your guests will leave saying, “That was fun—let’s do it again.”

Tools and Resources to Streamline Your Process

Preparing for a podcast interview can feel like a puzzle. You want to ask questions that make your guest shine—but digging through LinkedIn profiles and brainstorming unique angles takes time. The good news? You don’t have to do it all manually. The right tools can save you hours of research and help you craft questions that spark real conversations.

Let’s break down the best resources to make your interview prep faster, smarter, and more effective.

LinkedIn Research Tools: Find Guest Insights in Minutes

LinkedIn is a goldmine for guest research, but scrolling through years of posts and work history can be overwhelming. These tools help you extract the most important details quickly:

Crystal Knows – This browser extension analyzes a guest’s LinkedIn profile and predicts their communication style. Is your guest data-driven? Emotional? Direct? Crystal gives you tips on how to phrase questions to get the best responses. (Example: If your guest is analytical, ask, “What metrics do you track to measure success?” instead of “How do you feel about your work?”)
Phantombuster – Automates LinkedIn data extraction. Want to pull all of a guest’s recent posts, job changes, or shared articles? Phantombuster does it in seconds. You can even set it to notify you when a guest publishes something new—so you’re always the first to ask about it.
Dux-Soup – A simpler alternative for scraping LinkedIn profiles. It lets you download a guest’s work history, education, and even their connections (if they’re public). Great for spotting patterns, like if they’ve switched industries or worked at a company you both admire.

Pro tip: Don’t just look at their current job. Check their “Activity” tab for recent posts—they often reveal what your guest is really passionate about right now.

AI Tools Beyond ChatGPT: Fresh Angles for Your Questions

ChatGPT is great, but it’s not the only AI tool that can help you craft unique interview questions. Here are a few alternatives that bring different strengths to the table:

Perplexity AI – This tool is like a supercharged search engine. Ask it, “What are the most controversial opinions [Guest Name] has shared online?” and it’ll pull from articles, podcasts, and social media to give you a list. Perfect for finding hot-button topics your guest hasn’t been asked about in years.
Claude – Better than ChatGPT for long-form content. Feed it a guest’s LinkedIn profile and ask, “Generate 5 questions that uncover their biggest career failure and what they learned.” Claude’s responses are often more nuanced and less generic.
Jasper – If you want questions that match your podcast’s tone, Jasper lets you set a “brand voice.” For example, if your show is casual and funny, Jasper can rephrase stiff questions like “What’s your leadership philosophy?” into “Okay, spill—what’s the weirdest thing you’ve done to motivate your team?”

Try this: Use two AI tools side by side. Ask ChatGPT for 10 standard questions, then feed those to Claude and ask, “How can I make these more personal and unexpected?” You’ll get a mix of safe and bold questions to choose from.

Podcast Planning Templates: Organize Your Research

Even with the best tools, disorganized notes can derail your prep. These free templates help you structure your research and questions so nothing slips through the cracks:

Notion’s Podcast Interview Template – A customizable dashboard where you can:
- Store guest bios, LinkedIn links, and key achievements.
- Draft questions and tag them by topic (e.g., #career, #industry-trends).
- Add timestamps for when to ask certain questions during the interview.
Google Docs “Question Bank” – Create a master doc with sections like:
- “Icebreaker Questions” (e.g., “What’s a book you’ve gifted the most?”)
- “Deep Dive Questions” (e.g., “You mentioned on LinkedIn that [X] was a turning point—what happened behind the scenes?”)
- “Audience Questions” (leave space for listener-submitted questions).
Trello’s Podcast Prep Board – Use columns like “To Research,” “Questions Drafted,” and “Finalized.” Drag and drop questions as you refine them. Great for visual thinkers.

Why this works: Templates force you to think in stages. First, gather facts. Then, turn those facts into questions. Finally, sequence them so the interview flows naturally.

Books and Articles to Master Interview Techniques

Want to go beyond tools and truly level up your interviewing skills? These resources teach you how to ask questions that get memorable answers:

“The Art of the Interview” by Terry Gross – The legendary NPR host shares her secrets for making guests feel comfortable and getting them to open up. Her biggest tip? “Listen more than you talk.” (Bonus: Listen to her podcast, Fresh Air, to hear her techniques in action.)
“Never Split the Difference” by Chris Voss – A former FBI negotiator explains how to ask questions that uncover hidden truths. For example, instead of “What’s your biggest challenge?” try “What’s keeping you up at night?”—it’s harder to give a canned answer.
Article: “How to Ask Better Questions” (Harvard Business Review) – Breaks down the science of open-ended questions. One key takeaway: “Avoid ‘why’ questions early on.” They can make guests defensive. Instead, ask “How did you come to that decision?”—it feels less like an interrogation.

Quick exercise: Pick one technique from these resources and test it in your next interview. Did your guest give a longer, more detailed answer? If yes, make it a habit.

Putting It All Together

Here’s how to use these tools in your next interview prep:

Start with LinkedIn tools (Crystal, Phantombuster) to gather key details about your guest.
Feed those details into an AI tool (Perplexity, Claude) to generate unique questions.
Organize your questions in a template (Notion, Trello) so you can see the big picture.
Refine your approach with techniques from the books/articles above.

The goal isn’t to replace your curiosity—it’s to amplify it. These tools help you dig deeper, ask smarter, and create interviews that stand out. And when your guest says, “No one’s ever asked me that before,” you’ll know you’re on the right track.

Conclusion: Elevate Your Podcast with Smarter Questions

You’ve just seen 10 powerful ChatGPT prompts that can transform your podcast interviews. No more boring, generic questions like “How did you get started?” Instead, you can dig into your guest’s real stories—what they’ve learned, what they regret, and what they’re really excited about. These prompts help you find the gold hidden in their LinkedIn posts, past interviews, and even their failures.

Why Personalized Questions Matter

When you ask unique questions, three things happen:

Your guest feels valued. They’ll remember how you made them think, not just recite answers.
Your audience stays engaged. No one wants to hear the same old stories. Fresh questions = fresh conversations.
Your podcast stands out. In a sea of generic interviews, yours will feel like a real conversation, not an interview.

Think about the last time a podcast host asked you something unexpected. Did it make the conversation better? Of course it did. That’s the power of personalization.

Your Next Step: Try One Prompt Today

Don’t overthink it. Pick one prompt from this list and use it in your next interview. Maybe it’s:

“What’s a lesson you learned the hard way that no one talks about?”
“If you could debate one person in your industry, who would it be and why?”
“What’s a trend in your field that you think is overrated?”

See how your guest reacts. Did they light up? Did they share something surprising? That’s how you know it worked.

Let’s Keep the Conversation Going

Which prompt are you excited to try? Did you already use one and get a great answer? Share your favorite question—or your best interview moment—in the comments. The best podcasts grow when hosts learn from each other. So go ahead, test these out, and let’s make your next interview your best one yet.