Writing

How to Interview People: Terry Gross Teardown

Interviewing · Content Strategy

Before everybody had a podcast, there was NPR's "Fresh Air." Its host, Terry Gross, has long been recognized as a master interviewer.

What's that mean for us? If you're a fan of the show, you probably don't notice what Terry is doing or how she gets amazing insights from people. Which is good! The show is about the guest.

But if you really pay attention to the way she interviews people, you can get an incredibly valuable lesson in technique.

Here's a recent example. Terry is interviewing Ahmir "Questlove" Thompson, the co-founder and drummer of The Roots, the legendary hip-hop group that is now the house band for "The Tonight Show."

She's talking to him about a documentary he directed about a Black music festival in 1969. In the second act of the interview, she broadens the focus to Questlove himself. He's a fascinating person, and even though the thing he's there to plug is also really cool, she makes sure to step away from it and find out more about him.

Listen along below — the part we're dissecting starts at 19:00:

Fresh Air · NPR

So what?

We're obviously not interviewing people this famous, nor are we producing a mass-market entertainment and news show. So how can we use Terry Gross' interview with a famous musician to talk about business software?

Forget the topic entirely. Strip this down to its skeleton and it's an incredibly good example of two priceless interview techniques:

1. Changing the focus

At the 19 minute mark, Terry uses a question about costumes featured in the documentary to ask Quest about his own stage persona — she's asking him about what he does, shifting the focus to say "talk about you." But it's also framed as part of a large overarching trend:

"... Gladys Knight is wearing a skirt and a top, and The Pips are wearing beige matching suits. And, you know, Sly Stone is dressed like Sly, with his big glasses and the big gold chain. So what are your thoughts now about dressing on stage, how you want to be, and do you think you've changed at all?"

It kind of seemed like a weird segue at the time, but it worked. Questlove has a signature look: big afro with a vintage comb tucked into it. But very quickly after asking this, Terry indicates she's noticed he's not wearing the afro pick in his hair all the time anymore. This whole thing about costumes in his movie was really meant to ask him about the accessory!
Ask a big question to get to a specific answer. Especially if you think you know the answer, but you want them to say it.

2. Keep it rolling

Now she has him talking about himself — again, for our purposes, this is just any "secondary topic." Maybe you're interviewing an expert about their product, and you want to know about how this fits into the entire industry too. So you've made the transition, and they're talking. How do you get people to say more?

Less is more. If a subject is talking about the thing you want, it's your time to back off. Ask simple, open-ended questions. If they say something surprising, ask "really?" "How?" "What do you mean?" Repeat what they say, or leave silence — people will naturally fill silence.
Be ready to drill down on something profound or insightful. With four very simple questions and one very insightful one, Terry keeps him talking — and they go from "I don't worry much about fashion anymore" to how the pandemic has changed him, how he thinks about life, that he's a better person, and no longer worried about dying young.

QUEST: "… And now, you know, I, too, own a farm."

TERRY: "You do?"

QUEST: (He and his girlfriend got it during the pandemic to quarantine, but he loves it) … "I thought, like, chaos was the only way that I could exist. But now I embrace quiet, and I can hear myself think."

TERRY: "Do you have animals on the farm?"

QUEST: (There's wildlife, but no farm animals. However:) "My girlfriend made me get two cats to teach me empathy, which is helping."

TERRY: "I have to say, my cat is not famous for empathy. So my cat would not be a good teacher. So why do you need to be taught empathy?" (Note: She pivots to a very personal follow-up by first sharing something relatable about herself.)

QUEST: "... Just because I churn out great product might not necessarily mean that I'm also pleasurable to work with, you know, or that I'm big on or really good at communicating or expressing emotions and feelings ... I wouldn't even hesitate to say that had this not happened, I would have probably been on an express lane to the next life."

TERRY: "Really?"

QUEST: (A lot of his peers in music have been dying young, especially from health problems. He knew he needed to change his life.) "Like, I've lost over 100 pounds. I'm happier. You know, I'm just — I'm happy to be alive."

And that's how you get from one insight — this guy bought a farm? that seems interesting — to "I'm just happy to be alive" in four questions, made up of just 39 words.

Will we all be interviewing a famously verbose artist about life and music and film? No. But you can absolutely take these interview tips to a marketing context.

Takeaways

Change the focus, but don't obsess about the perfect segue.
Asking a big question can get a specific answer — especially if you know what you want them to say.
Keep them talking during the good parts with short, open-ended questions (or even silence).
Always listen for the profound or the insightful and be ready to dive in.
Bring yourself into the conversation as an observer to ask about someone else's internal thoughts or problems.