5 Witty Interview Questions That Will Instantly Make You a Better Host

Hi there! 👋 I’m Pat Flynn. As a content creator who’s passionate about simplifying, energizing, and monetizing the creative process, I’ve been hosting podcasts and conducting interviews for quite a while now. Along the way, I’ve learned a thing or two about what makes an average interview forgettable and what makes a great one binge-worthy. Spoiler alert: it all boils down to the questions.

If you’re diving into interviews—be it for podcasts, YouTube videos, or even written pieces—it’s your job as an interviewer to ask questions that go beyond the surface. In doing so, you not only connect deeply with your guest but also keep your audience engaged and hungry for more.

In this guide, I’ll walk you through my five favorite questions to ask during interviews. These aren’t your typical cookie-cutter questions. Instead, they’re designed to spark emotion, unveil untold stories, and create episodes that are noteworthy enough for your audience to share. Stick with me to the end, because the last one is a real game-changer.

Grab your microphone, notepad, or camera because these tips are about to take your interview game to the next level. Let’s get started! 🎙️

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1. Why? The Most Powerful Question

We’ve all heard it before—this small, three-letter word can carry an enormous amount of weight. And sure, maybe we associate “Why?” with an inquisitive toddler bombarding us with endless questions 🙃, but trust me, “Why?” is your most powerful tool as an interviewer.

Why It Works:

When your guest answers a question, their response often scratches the surface. Following up with “Why?” helps you dig deeper into their thought process, decisions, and emotions. This is where the gold lies.

For instance:
Guest: “I decided to leave my corporate job and pursue my passion for painting.”
You: “Why did you feel like it was the right time to leave?”

This prompts more profound storytelling. Maybe they share an emotional anecdote about a life-changing moment that pushed them to pivot. Boom—instant connection with your audience.

Pro Tip: Don’t overuse “Why?” Just like salt in a recipe, a sprinkle will make the conversation flavorful, but too much might overwhelm the dish—or worse, make your guest feel interrogated!

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2. What Happened Next?

Ah, one of my personal favorites! This one’s a gem for when your guest is building momentum with a great story. When they momentarily pause, they might not know whether they should continue or stop talking. Here’s where you step in and ask:

Why It Works:

This simple question gives your guest permission to keep telling their story. It’s a subtle nudge that shows you’re listening and genuinely intrigued. Plus, it keeps the energy going without you needing to come up with an entirely new question.

Take, for example:
Guest: “I was standing on stage in front of 5,000 people, and then—”
You: “What happened next?”

They’ll likely recount an unforgettable moment that your audience will cling to. Magic happens when you open the door for more storytelling.

Pro Tip: Pair “What happened next?” with strategic pacing. Pause naturally after asking it, so the guest feels comfortable and encouraged to dive back in.

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3. How Were You Really Feeling?

Interviews often aim to extract info, but the most memorable ones tap into emotion. Emotions are what resonate with your audience—they’re what make people think, reflect, laugh, or even cry. And that’s where this question shines.

Why It Works:

Asking about feelings invites vulnerability and authenticity. It makes the interview more human and allows the guest to share relatable, emotionally charged insights.

For example:
Guest: “When we launched the campaign, it failed miserably.”
You: “How were you really feeling in that moment?”

Imagine the layers you can uncover with this question! The guest might reveal their fears, personal struggles, or newfound resilience—moments that stick with your audience long after the episode ends.

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4. The Mirroring Technique

This isn’t so much a question as it is a psychological tactic, but it’s one of the sneakiest ways to get your guest to share more without forcing them. I picked this one up from Chris Voss’s iconic book Never Split the Difference (if you haven’t read it, trust me, you’re missing out).

How It Works:

Simply repeat the last few words of your guest’s sentence with an upward intonation, almost like a question.

Example:
Guest: “I’ve been going live on YouTube for over 200 days straight.”
You: “200 days straight?”
Guest: “Yeah! It actually started as a 30-day challenge, but I stuck with it because the audience engagement kept growing…”

Notice how this lets you mine for more information without sounding pushy. The guest feels validated, the conversation flows naturally, and you uncover juicy details. 🎯

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5. Tell Me About a Time…

If there’s one tool every good interviewer should master, it’s the story-prompt question. People LOVE stories—stories captivate us, teach us lessons, and make us feel something. When you phrase a question with, “Tell me about a time when…,” you give the guest a chance to delve into narrative mode.

Why It Works:

Stories are what audiences remember. A list of facts or tips fades away quickly, but a well-told story? That sticks. Plus, story prompts allow your guest to share real and unscripted moments.

Example:
You: “Tell me about a time when a tech glitch nearly ruined your livestream.”
Guest: “Oh, you’re going to love this one. So, I was mid-presentation for a paid webinar, and suddenly, my entire laptop crashed…”

Cue a memorable story that not only entertains but provides actionable insight for your audience.

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Why Active Listening Is Key

Let’s face it—being a great interviewer often isn’t about what you say. It’s about what you don’t say. The best podcasters and YouTubers are excellent listeners. They know how to set up a great question and then get out of the way.

When you actively listen:

• You build rapport with your guest.
• You instinctively know which follow-up questions will add value.
• You make the guest feel like they’re the star of the show (which they should be).

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Your Takeaways

These five questions—and tactical approaches—are tools you can start using today to elevate every interview you host. Whether you’re recording a YouTube video, running a podcast, or conducting a professional Q&A, these tips will help you:

• Stand out as an interviewer.
• Pull deeper, more emotional stories from guests.
• Captivate your audience with content that’s worth sharing.

Have you tried any of these techniques? Which one resonated most with you? Let me know in the comments below—your feedback always inspires me!

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Need More Help Perfecting Your Interview Game?

Here’s a secret weapon I’ve integrated into my interview process: Ninjafy AI. It’s like having a real-time assistant whispering the right follow-ups in your ear. Seriously, Ninjafy’s customization features and live-audio analysis have taken my preparation to the next level. If you’re serious about nailing interviews, I highly recommend checking it out.

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Make sure you succeed in every interview.