Interview Structure 4: Serendipitous

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You’re reading an excerpt of Stop Asking Questions, by Andrew Warner, a veteran podcast host of 2000+ episodes. The book explains how to lead high-impact interviews and learn anything from anyone. Master the craft of interviewing with this complete digital package. Purchase now for lifetime access to the book and extensive audio and video resources.

This interview format was popularized by Joe Rogan, the comedian-turned-podcaster who signed a $100M deal to make his show exclusive to Spotify listeners. Rogan can talk to his guests for more than three hours per interview, often with a whiskey in his hand. His conversations bounce between topics like discipline, nutrition, drugs, and exercise, without much more connecting them than Rogan’s interest.

These types of interviews seem to lack structure, but when I studied Rogan’s transcripts, I saw a clear methodology. I call these interviews “serendipitous” because the host moves quickly through topics, looking for surprise gems. They’re like a pub crawler who goes from bar to bar, spending more time in the ones that are fun and moving on the moment things get stale.

A good example is Rogan’s interview with Elon Musk, the billionaire behind SpaceX and Tesla. Listen to how fast they zip through topics. They take just seven seconds to greet each other. Then Rogan asks about flamethrowers. Musk gives answers I’ve heard him give before, so three minutes and 45 seconds later, Rogan ditches the topic.

“Forget about the flamethrower,” he says. “How does one decide to fix LA traffic by drilling holes in the ground?” He moved on to Musk’s Boring Company, which aims to ease Los Angeles traffic with tunnels.

Five minutes later, Rogan says, “I just don’t know how you manage your time,” and switches to the topic of productivity. Finally, Rogan hits on a question about artificial intelligence—the opportunities and threats of increasingly intelligent computers. Discovering a topic that’s fresh and interesting, Rogan settles into it for 44 minutes.

That’s the way these serendipitous interviews work. Topics are disposable. The host moves quickly through multiple subject areas, looking for what’s new and fascinating.

How does Rogan keep the conversation about AI interesting for the full 44 minutes? That’s longer than a sitcom, and sitcoms have teams of writers. How does he hold people’s attention for that long?

The answer is he doesn’t. And that’s by design, which brings us to the next important element of serendipitous interviews: their purpose.

Alex Blumberg, co-creator of NPR’s Planet Money and the co-founder of Gimlet Media (acquired by Spotify), has said a big reason people listen to audio shows is companionship. For the serendipitous style of interview, the audience doesn’t want their attention held tightly. They’re doing other things while listening, like cooking, walking the dog, or exercising. They don’t want to focus the way they would during a college lecture or even a sitcom. They want the company of friendly banter while they go about their day.

I don’t do serendipitous interviews. I’m too hard-charging for that. I have to have a goal and a process for getting there. Hitting record and hoping for magic would be like asking Michelangelo to throw paint at a wall. That style worked for Jackson Pollock, but Michelangelo was more structured.

Still, I study these interviews to help me improve my style. Once I understood how these interviews worked, I incorporated their approach into my more structured approach. For example, I learned from Rogan that you don’t need to exhaust a topic. It’s OK to move on to something more interesting.

This more flexible attitude helped me interview David Rubenstein, billionaire founder of the Carlyle Group. I wanted to ask him about how he built his private equity firm, but the combination of finance and politics involved was outside my podcast’s focus. I also felt too much resistance from him about going back to discuss a company he was no longer running day-to-day. So I allowed the conversation to keep shifting. We talked about how he prepared for the interview show he hosts on Bloomberg, his firm’s use of political influence, his Jewishness, his pledge to give away the majority of his wealth, his leadership book, and so on.

I kept a watchful eye on our mutual interest for each topic and the level of depth in David’s answers. When either of those seemed to flag, I allowed myself to move the conversation to another topic.

Listen: Serendipitous Interview Structure

Interview Structure 5: Panel Discussion7 minutes

Panels tend to be a refuge for the lazy. That’s why they’re painful for audiences to sit through. It’s true of both traditional in-person conferences and emerging online panels, like the social audio pioneered by Clubhouse and video summits done by virtual conferences.

To understand the problem with panels, let’s look at a conference I spoke at. As I waited in the green room for my turn on stage, I watched the conference organizer introduce a moderator to his panelists moments before they were to go on stage. The moderator laughed as he told his panelists, “I prefer leading panels to giving presentations because I hate the work of putting slides together.” The panelists nodded in agreement. They masked their laziness as a hack, congratulating themselves for getting attention by being on stage, without doing any work.

On stage, the moderator sat limply as he tossed softball questions, like, “Could you tell us about yourself?” Even when they talked for too long or were too self-promotional, he let them go on. Many moderators blame their panelists for not knowing how to give good answers instead of taking responsibility as the leaders of the conversation.

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