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Marketing Showrunners

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By: Jay Acunzo on May 14th, 2019

The Interview Magic of Stern, Gross, Simmons, Glass, & More: 9 of Their Best Questions

Creating shows to build passionate audiences provides our companies undeniable benefits: we hold attention, gain trust, increase the lifetime value of our existing audience, and decrease customer acquisition costs thanks to word-of-mouth. However, creating and growing a show or a network of shows can be a total mess of parts and pieces. Show Bites is our series of quick-hitting posts where we try to snap off a tiny little piece of the overall work and rethink it in order to improve.

The Show Bite: Interviewing Guests

I’ve written before about why interviews are more like a dance than a straight march forward. As show hosts, we have to care about the final product and balance a number of things we care about during a given interview: our company’s goals, our goals with the show and for the final episode, our own performance as hosts, the guest, and of course, the most important stakeholder of all: our listeners. Serve them better, and everybody else wins. But that doesn’t mean your guest is great at delivering material that forms a compelling interview or story. That’s the role of a great interviewer.

When we interview someone, we’re in “extraction” mode. Our jobs are to extract content from the guest — not in an evil scientist with a big metal syringe kind of way (though points for staying in character during your podcast, Larry), but more in that coaxing, friendly, please-oh-please share some magical moments as a guest … kind of way. And in this zig-zaggy dance that is an interview, the questions we ask make all the difference.

The Misconception: Questions Should Be Clever

Thanks to many internet-famous hosts who shall remain nameless in this blog post, there seems to be a growing movement of show hosts who want to create some kind of clever scenario-based questions for their guests. You’ve heard them before as a listener, I’m sure. They sound something like these:

  • If you were on a desert island, who are three people you’re taking with you?
  • What’s the book you’ve given most as a gift?
  • What’s the one thing about your morning routine that you absolutely can’t live without?
  • How much wood would a woodchuck chuck if a woodchuck could chuck wood? Also, did he go viral?
  • If you could run a billboard that says just one thing on it for the world to see, what’s on the billboard?
  • And of course … lightning rounds. (Oh, lightning rounds. You are to interview questions what candy corn is to desserts.)

Don’t get me wrong: Almost any question above can be used tactfully given the right circumstances. (Side note: Under no circumstances should you ask the woodchuck question to a badger. Just trust me.)

Still, those interview questions aren’t easily slotted into a conversational flow. They feel like, well … an interview! But the best interviewers on the planet help the guest forget a microphone is even there. People like Ira Glass, Jad Abumrad, Terry Gross, Howard Stern, Larry King, Ellen Degeneres, and Bill Simmons don’t look for clever, heuristic-based questions. They ask stuff in context. 

Great interview questions aren’t clever. They’re simple.

Consider Instead: Simple Questions to Ask in the Flow of Conversation

Tell me about… (Surprisingly effective despite not technically being a question. Kara Swisher is the master of using this one. It keeps things open-ended and demands specific responses.)

How did it feel when…? (Just like the above, with one key difference: Instead of getting story details and facts, you’re getting reflection and emotion. Capturing both creates the richest episode possible.)

Can you share an example? (Pulled straight from my last article on the 3 questions to ask to get irresistible material from guests. This one is breathtakingly effective and SO easy to forget to ask. Lots of guests give generalities on podcasts or video shows. Don’t let them wriggle away without giving you actual examples.)

What do you say to people who…? (An awesome way to get someone to address criticism or another way of seeing the same topic without pitting you against the guest. If you challenge them directly, you risk losing them. This gently nudges them to consider differing points of view and speak to them. That’s huge for a well-rounded, nuanced interview.)

What was the least/most/best/worst XYZ? (Using superlatives almost always delivers a thoughtful reply. They may need to think about it, which is fine and should be encouraged overtly by you in case they feel rushed and give you a mediocre answer.)

Was it more like X or Y? (This helps you frame anything they said, especially complex concepts, as two simple things. Yes, life isn’t that black or white, but it helps listeners place something on a spectrum, where X is on one end and Y is on the other.)

What changed when…? (A great one to ask to get them to analyze a situation, and to convey the movement forward of a story’s action or their own thoughts and emotions, given that action. Since I interview almost exclusively people in business, I’ve stopped asking them to describe what their product is or does and started asking, “What changes when someone uses your product?” Strikingly better replies.)

What did you think it was going to be like, and what was it actually like? (Hat tip to the great Alex Blumberg for this one.)

And now (drum roll, please), the world’s all-time best, most-powerful question to ask — a question so common and so beloved that once I reveal it, you’re gonna hear it spoken by public radio personalities and famous podcasters the world over, like pointing out a certain type of car and suddenly seeing it EVERYWHERE.

That simple but oh-so-great interview question is…

How did that make you feel?

And there you have it: Nine simple yet magical questions you can ask to capture better audio and video responses from your guests. Remember: If a guest isn’t giving you great answers, that’s not their fault. It’s yours.

Now that you realize that, let me just ask you quick: How does that make you feel? 😉


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Founder of Marketing Showrunners, host of 3 Clips and other podcasts and docuseries about creativity, and author of Break the Wheel. I’m trying to create a world where people feel intrinsically motivated by their work. Previously in content marketing and digital strategy at Google and HubSpot and VP of brand and community at the VC firm NextView. I write, tinker, and speak on stages and into microphones for a living. It’s weird but wonderful.

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