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Mastering the art of the interview—with the master interviewer

New York Times Magazine columnist David Marchese breaks down the art of conversation.

Journalist David Marchese has interviewed so many of the world’s most creative and interesting people, it seems a bit silly to ask him to pick a favorite. In the last few years alone, he’s spoken with Alex Trebek; Billy Joel; Erykah Badu; Emma Thompson; John Krasinski; Maggie GyllenhaalChimamanda Ngozi Adichie; Peter Dinklage; Sarah Silverman—the list goes on and on. His interview with talk show icon David Letterman seemingly broke the Internet when it was published in 2017. His chat with music legend Quincy Jones was read by more than 1.5 million people in the first 24 hours after it was published; other media outlets deemed it “myth-shattering,” “jaw-dropping,” and one of the “most interesting interviews ever.” He asked People Nerd extraordinaire Terry Gross what goes through her mind when she’s asking a question, and screen legend Isabella Rossellini about the time her mother (the iconic Ingrid Bergman) explained “the birds and the bees.”

Starting next month, Marchese will take on the famous “Talk” column for the New York Times Magazine—in making the announcement, editor in chief Jake Silverstein called him “one of the most prolific and profound interviewers in the country.” He went on to say: “David’s hallmark is intense preparation, humor, intelligence, honesty and an uncanny ability to get fascinating people to open up, often about things they’ve never publicly discussed before.”

dscout sat down with Marchese to find out what the master interviewer says makes for the best kind of conversation.

dscout: You’ve interviewed so many of the major artists and cultural figures—as well as a number of other “master interviewers”–and in many cases, you’ve gotten them to open up in a way that they really haven’t previously. Where did that interest in people come from? Have you always been kind of a people nerd? #

David: It’s funny, I don’t really think of myself as a people nerd. But there’s obviously enough evidence in my life to suggest that as a journalist I’ve gone down this particular road. And I find that I often get in conversations with cab drivers, or the cashier at the grocery store, or the person at the coffee shop. So it turns out I do sort of like talking to people—but that really is a change. I used to have a hard time talking to strangers. In college, my least favorite thing was having to give a presentation in class. But going into the line of work I went into, I was forced to practice interacting with people I didn’t know over and over again. That yielded something fruitful. It turns out if you do that hundreds of times, you get more comfortable with it. In my case, it revealed to me that I actually sort of enjoy it. And this maybe sounds a little new-age-y, but about 10 years ago I started meditating regularly, and I think that helped too.

How so? #

Well it’s always a little hard to know how much of a change to ascribe to something like meditation, but it helped me become better at being in a conversation and outside of it at the same time. Meditation is essentially practicing managing your thoughts. It helps me be simultaneously aware of someone’s reaction to something while I’m saying something else, and also think about what I want to ask you 10 minutes from now and where the conversation should go.

Is meditating pretty common for journalists? Do you know others who do it? #

I don’t really. I’ve gotten emails from other journalists wanting to know about it, but I don’t know if any have tried it themselves. But mindfulness and meditation are kind of buzzy right now, so people are a little bit more curious than they used to be.

As someone who used to have a hard time talking to strangers—was it nerve-wracking when you started interviewing people? The first time you went in and sat down with someone famous, were you nervous? Did you get any useful tips from anyone, an editor, a journalism professor? #

The funny thing is I never had any instruction or education in interviewing. I think it’s rare that anyone does, which is strange because the interview is the building block of so much journalism. It’s the thing you build stories on. Yet it’s rare that anyone teaches how to do it in a systematic or thoughtful way.

But yes, the first time I sat down with someone famous I was nervous. For one of my first pieces for Spin I interviewed Vampire Weekend, who were a new band at the time. I felt like I didn’t have much control over the conversation. I was flustered by any sort of pushback. It took a long time to master those feelings—it was really a matter of being forced to practice, and naturally getting more comfortable.

One clarifying event was a long interview I did with Lou Reed, who was known for being combative in interviews. I sat down with him and he was insulting and aggressive, and not only did he not really answer my questions but he took issue with the premise of a lot of the questions. I finished it thinking, “That really went badly.” But afterward, when I was putting it together, I could see that while I was bearing the brunt of a lot of his aggression in the interview, the piece actually hadn’t suffered journalistically. It turned out very well. I think it’s a natural human desire to want to feel that a person liked you after you’ve had a conversation with them, but in terms of what an interviewer is supposed to be doing, that’s not always the goal. It’s important to keep that in mind.

How much preparation goes into a big sit-down like that? You obviously think about questions in advance, but in the moment, how much are you using a script as a guide and how much are you letting the conversation go where it needs to go? #

It depends how much time I have. I try to do as much research and preparation as I possibly can. One of the goals of the conversation is to let it go where it wants to go, and let the subject lead you to the areas they’re going to have the most insight on and interest in. You don’t want to circumscribe the parameters of the conversation, but you don’t want them to just sort of float off into the ether. If I’ve done as much research as possible there are very few places the person is going to go that I can’t tie back to something interesting. So even if I don’t end up drawing on all of the research I’ve done, I have as many cards to play as possible. You don’t want to be in a position where someone mentions something and you don’t know what they’re talking about. But if they reference, say, a song they’ve recorded, and you can draw on something you know about it, you increase the likelihood they’re going to tell you more than what they’ve said in the past, because you’ve just demonstrated that you take them and their work seriously. It makes the conversation more akin to one they might have with someone who actually knows them. When you’re having a conversation with your friends, you take for granted they know things about you, and you talk in a more casual or intimate way. I think the same applies to interviews. If, through research and preparation, you can show that you have a grounding in and a respect for what they’ve done, it goes a long way toward getting to intimacy more quickly.

I think the same applies to interviews. If, through research and preparation, you can show that you have a grounding and a respect for what they’ve done, it goes a long way toward getting to intimacy more quickly.

What about if you’re asking someone something that’s difficult, or something you can see they’re hesitant to answer? Is there a way to frame a question in a way that makes them feel more comfortable? #

Obviously you can’t always get somebody to talk about something that they don’t want to talk about. But the one thing that I’ve consistently found helpful is when I’ve said to the subject like, “Look, I know this is hard to talk about,” or, “I know this is something you might not want to talk about,” or even saying “This is not an easy question for me to ask.” When I’ve done that, it’s very rare somebody still comes back and says, “Let’s just move on. I don’t want to talk about that at all.” I think if you’re being explicit to the person about the fact that you understand that your question is putting them in a difficult position, or might make them feel uncomfortable, or even acknowledging to them that it’s uncomfortable for you to ask it—that demonstrates emotional understanding. You’re not someone who is only interested in pushing their buttons for the sake of your job. If you can show that you’re not just a clinical question-asking robot, my experience is that people then usually give you something back. There’s an emotional reciprocity in that exchange.

One of the people you’ve interviewed is Terry Gross, someone who is thought of by many people to be kind of the master interviewer.  #

Talking shop with her was really interesting and useful. It was nice to be able to ask someone, “So what is actually happening in your mind when you’re asking a question?” And she had a specific answer and I knew exactly what she was talking about. It was sort of, oh right, it’s these three things. What they’re saying, what you want to say next, and how it might connect to something that you’re going to ask down the line.

And she also talked about losing her train of thought, which was something I could relate to—that sometimes you’ll be asking a question, and then in the middle of asking the question realize you’ve forgotten what your actual question was but somehow you just keep saying words until the question comes back into your head… and you sort of bail yourself out. And I was like, “Oh yeah. I’ve heard that so many times.”

So what about those moments during an interview where your brain is working at multiple levels—when you’re thinking about the question that you have just asked, what the person is saying, and how you might connect it to a question down the road. Is there a practical way you can kind of prepare or set yourself up to do that? #

It’s a little hard to say in that specific way because it’s sort of cognitive processes that I don’t have the vocabulary to describe it in a useful way. But one thing I find very, very helpful is to really try and commit questions or topics to memory. So I’ll actually go over my question notes 35 or 50 times, just read them over in the hope of searing them into my brain so that when somebody brings up a topic, rather than having to riffle through five pages of printed-out notes and hope you can find the thing, in the hopes that it’s just actually within your brain’s recall, and it sort of pops up by nature of association. And my experience is that that works.

I really try not to refer to notes during an interview. I try my best to just be able to maintain eye contact and have it seem natural and not be looking at notes. And I often find that after the interview, when I’m going back over stuff, even if I haven’t looked at my questions during the interview, I’ve asked 95% of the things that I wanted to ask as a result of committing them to memory. I really think that’s helpful, and it sort of gives you the flexibility of if the conversation goes in a certain direction, just like, again, a card to play. Like you have that card in your hand, and hopefully you don’t forget it’s in your hand. Memorization is a very, very powerful tool.

Another one of your really memorable sit-downs was with another fellow interviewer—David Letterman. And it kind of happened when he wasn’t really doing a whole lot at the moment—it was before his Netflix special, right?  #

Yes, about a year after he retired. The nature of that interview was a little bit surprising to me, because Letterman doesn’t necessarily have a reputation as the warmest guy. He was that way on his show—kind of prickly and sarcastic. So I was prepared for him to maybe not be that forthcoming or just kind of be not the easiest interview. But I really think that getting him when he wasn’t in the middle of a bunch of other stuff and when he hadn’t talked expansively in the recent past was beneficial. It really seemed like he just had things he wanted to talk about—politics or reflecting back on his career or his life now. The depth of his answers about certain things was surprising. I’d asked him a question about his son, and whether he really had a sense of what his dad’s career was like. And he just had these intimate, funny stories about him and his kid. That his son would sort of roll his eyes when Letterman would complain about his hamburger order or something. He’s not someone who was known for divulging a lot about his personal life before. So when he was talking about that stuff, it was clear to me that he was being open in a way that I wasn’t expecting going into the interview. And I think that openness is a lot of what people responded to. Seeing him unfiltered.

Well, that’s the hallmark of the David Marchese interview, isn’t it? #

Ha. 

Let’s talk about process and the work that comes after an interview. A lot of people seem to think that an interview is just a transcription. The journalist has come up with these brilliant questions and asked them in the right order, and the interviewee has come back with these completely coherent answers, and those go verbatim into the piece and it’s done. But that’s not actually how it really works. There is quite a bit of crafting of the story after you’ve done the interview, figuring out the arc of what was said and what the meat of the piece is going to be. But that’s sort of hidden work, at least to the people reading the finished piece. #

There’s a huge amount of work that happens after the conversation has occurred. In terms of verbal filler alone, there’s so much you have to cut out. Or if someone changes verb tense halfway through an answer. That’s why, more and more, at the end of interviews publications include the disclaimer, “This conversation has been edited for clarity.”

But beyond that, I think of my job as to deliver the most insightful, interesting interview that I can. Not everything that was said during the actual conversation ends up being interesting or insightful, and some of that is even a little bit by design. If it seems like someone is a little guarded, there might be 15 minutes of me asking them fairly gentle questions in an effort to soften them up. Obviously all of that is cut out of the final interview because it’s not interesting to read those answers.

You’re creating an arc. It’s a form of storytelling. You don’t want a conversation to feel meandering and disconnected. You’re trying to create something that has narrative momentum and tension and little moments of release.

And generally you want to start with your best stuff. So even if it’s something particularly sensitive or controversial, you move that up toward the top of the written interview. As you said, you’re creating an arc. It’s a form of storytelling. You don’t want a conversation to feel meandering and disconnected. You’re trying to create something that has narrative momentum and tension and little moments of release. It may not be in the exact order of the actual conversation. If the piece needs a moment to breathe, you might move something a little lighter, a joke, up a bit. You’re never changing the words or the meaning of what someone says or reconstructing something so the meaning could be construed differently. I’m very strict about that. But I’m equally as strict about only including the stuff I feel is insightful or contributing to the larger shape of the piece.

When you’re going over a piece, you’ll get a sense if something is boring. Sometimes the temptation is to think “I don’t want to deal with cutting all of that out.” But I think it’s very important to cut out all the boring stuff. You can accomplish a lot that way.

This conversation has been edited for clarity.

    Author-Bio
    Carrie Neill

    Carrie Neill is a New York based writer, editor, design advocate, bookworm, travel fiend, dessert enthusiast, and a fan of People Nerds everywhere.

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