What Questions Make the Best Podcast Interviews? | Jason Cercone: Business Podcasting Consultant

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How to Create Conversations Your Audience Remembers

What questions make the best podcast interviews? The answer starts with understanding your guest, doing your homework, and asking questions that encourage them to share experiences they haven’t discussed a hundred times before.

If you’re hosting a podcast for your business, every interview gives you an opportunity to build relationships, demonstrate your expertise, and create content your audience wants to consume. The questions you ask play a major role in how well you accomplish those goals.

AUTHOR’S NOTE: If one of the objectives of your business podcast is to position yourself as an authority in your industry, you should have at least a 3:1 ratio of solo content to guest content. If you lean too heavily into guest-driven content, your audience may see you as someone who interviews experts, but isn’t an expert yourself. But when you do welcome guests on your show, make sure you’re adhering to the advice found throughout this article.

Move Beyond the Standard Podcast Interview Questions

As an example, think about how often authors hear questions like, “Tell us about your book” or “What was it like writing it?” These questions can get the conversation started, but guests who regularly appear on podcasts have probably answered them countless times.

Their responses may be polished and informative, but you could miss the personal stories and valuable insights that make an interview memorable.

Instead, dig into your guest’s experiences and ask questions that invite them to explore their work from a different perspective. For example, rather than asking an author about the writing process, ask whether they ever reached a point when they wanted to throw the entire manuscript away and start over.

That question opens the door to honest stories about unexpected challenges, creative frustration, and the lessons learned along the way.

When your guest responds with, “Nobody has ever asked me that before,” you know you’ve created an opportunity for a more meaningful conversation.

How to Prepare Questions That Generate Better Conversations

This requires preparation…but you don’t need a 20-question script sitting in front of you throughout the recording.

Start by researching your guest’s background, expertise, work, and experiences. Identify topics that align with your audience’s interests, then develop 3-5 thoughtful questions that can guide the conversation.

Leverage these approaches when preparing for your next interview:

Ask about unexpected challenges your guest encountered while pursuing a goal
Explore decisions that changed their approach to business, leadership, or their craft
Invite them to share a lesson they learned through an experience they didn’t anticipate
Dig deeper into a specific accomplishment to understand the process behind the result
Ask follow-up questions that encourage your guest to explain what happened and why it mattered

These questions give your interview direction while leaving room for the conversation to develop naturally.

Active Listening Makes Your Podcast Interviews Stronger

Preparation establishes a foundation, but active listening helps you recognize the moments worth exploring.

Pay attention to what your guest says, how they describe an experience, and which details deserve another question. If they mention an unexpected obstacle, ask what happened next. If they describe a difficult decision, explore what influenced their thinking.

You don’t need to rush through every question on your list. A thoughtful follow-up can uncover a valuable insight that your original outline never anticipated.

Those moments also create opportunities to repurpose your podcast into short-form video clips, longer video segments, pull quotes, blog posts, and social media content.

Create Podcast Interviews Worth Revisiting

Your goal should be to create the best possible conversation you and your guest can have, giving your audience practical insights, compelling stories, and reasons to return for future episodes.

When you prepare with intention, ask questions that go beyond familiar talking points, and remain engaged throughout the conversation, you give your guests an opportunity to take part in something meaningful.

Before your next recording session with a guest, ask yourself one question: What could I ask that would help my audience learn something they haven’t heard before?