Q&A: Anna Sale on asking questions about death, sex, money

A great interview is one of the journalist’s most powerful tools. It can be informative, entertaining, thoughtful. For the next five weeks, the Columbia Journalism Review and MaximumFun.org will broadcast conversations with some of the world’s greatest interviewers. Hosted by NPR’s Jesse Thorn, the podcast, called The Turnaround, will examine the science and art of journalism.

This episode features Anna Sale, host of Death, Sex & Money. An edited transcript is below.



Jesse Thorn: Your show, Death, Sex & Money, is a very particular kind of interview show. I thought I would ask you to describe it because it sounds like the kind of show that has a real tight solid elevator pitch.

Anna Sale: It does have a tight elevator pitch, but I think it’s actually much broader than the way it sounds. The idea for the show when I pitched it was I wanted to have an interview show where you didn’t skip over the actual meat of what I consider to be the things that actually drive our decisions in life. And that is relationships, money, and the fact that we’re all going to die. So, it’s a personal interview show, but I try to make sure that we don’t skip over those parts, and that I focus on those parts. Like if we’re talking about a moment of career transition, I want to know how someone supported themselves when they made the leap. Or if they had a huge change in their life, how that changed their relationship. So that was the idea. Everybody deals with death, sex, and money. So it’s a show that you can interview people who are really famous and also people who listeners haven’t heard before.

Jesse: That’s like private stuff, Anna.

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Anna: I know. But it’s stuff that it’s nice to hear other people talk about.

Jesse: Before you started this show with WNYC, you were a reporter, right? What kind of reporter were you?

Anna: I covered all sorts of things for almost 10 years, just in public radio newsrooms. But mostly focused on politics and towards the end of my time, mostly political campaigns.

Jesse: When you talked to people in politics, did you ask them about things that were closer to what you do now?

Anna: Yeah I did. I mean I did it in two ways. In one way, covering elections is pretty much what I do now. Because when you’re talking to voters, you are trying to get at what are the core, hot, emotional issues that are driving them to make decisions. So I had a lot of conversations with voters about whether they felt like they had enough money. How their politics changed because they were now a divorced woman in their 50s and had to send their kid to school. Actually my conversations with voters were a lot like what Death, Sex & Money has become. My conversations with the candidates were not because candidates are trained to not kind of go to vulnerable places. But I always tried. I remember covering the New York City mayoral election and talking to Bill de Blasio about how he felt comfortable basically using images of his kids in his political campaign, when he talked about how central his family was to his identity and his political identity, whether he thought he was putting them in some way possibly in harm’s way by putting them up for public consumption. So those were the kinds of questions I found interesting as a political reporter as well.

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Anna: One of the really important traits of an interviewer is to communicate to the person you’re asking questions of that you are sincerely curious and there’s a reason you’re asking them these questions. Because your interview is only going to be as good as the person’s willingness to participate. I sort of think of it as you’re kind of creating this together. You know with the start of every Death, Sex & Money interview I say, “You know this is what the name of the show is, but this is why we explore these topics. It’s because these are things that everybody goes through but also can feel the most isolated around. So I’m going to ask you about these things, but it’s not just to be provocative. I’m looking for places of resonance.” And so I explain that at the beginning, and I think that does help make the person I’m talking to feel more comfortable opening up. Because it’s in service of something, it’s not just me poking and trying to expose. It’s more about exploring something together.

Jesse: Do people believe you when you say that?

Anna: I think so. I also say, “And if there’s something I ask you that you don’t want to talk about, you can say that.” And so, I think by giving permission to sort of not take away all their power, it feels more comfortable. And I will say my producers and I take it really seriously that we’re going to treat these interviews with respect, and we’re not going to then have sort of tabloidy headlines. Like, we try to be sensitive to the stories that we’re telling.

Jesse: Because you’re asking about such a particular thing and something that often people are uncomfortable asking about, do you know what’s coming? And to what extent are you really flying blind?

Anna: Well I think it’s more flying blind when we’re talking to somebody who’s well known, because most often when those interviews get scheduled, none of my producers have an opportunity to talk to the person ahead of time. When I get into a room and I’m beginning the conversation and talking about what the show is and the kinds of things I want to talk about, that’s our first interaction. I can go in with the plan and the things that I want to explore. But I really have no idea how game someone who’s famous is going to be. And sometimes it’s incredibly surprising and satisfying what they have to say, and the interviews can go places I never expected. But I would say with people who aren’t famous, producers on the show get to talk to [them] ahead of time and get a sense of this story. So, there’s a little bit less of a question of, “What are we going to be allowed to talk about?” But still, I think the most interesting interviews preserve that sense of spontaneity and don’t have that rehearsed feeling. So I try not to talk to anybody ahead of time before we’re rolling because I like the freshness of that interaction.


Jesse: Do you have arrows in your quiver when you’re talking to someone? Like, if you run out of juice.

Anna: I mean that’s where the premise of Death, Sex & Money is really helpful because I can come back to, “And as I told you, the name of the show is Death, Sex & Money, so I’m going to ask you about death, I’m going to ask you about sex, and I going to ask you about money.” And then I will ask big, broad questions about if there’s someone in your life that’s died that’s left you with regrets. I ask about what sex is like at this point in their life if they’re in their 50s or if they’re in their 20s. I ask if they’re making more money this year than last year. And those are sort of just simple questions. But because the premise of the show kind of gives me permission to ask these questions that you probably wouldn’t ask in another interview, they can open up new avenues. We don’t always use the answers to those questions, but sometimes it’s really interesting. I asked Dan Savage about money, and he went on and on about how that was the single biggest point of tension in his marriage. Because he doesn’t like to spend money and his husband does. And it was just interesting to me because that’s not often what I hear Dan Savage talking about. I hear him talking about how to negotiate your sex life with your partner. To hear him talk about how to negotiate online spending with your partner was new.

Jesse: You give people the opportunity to say to you, “Oh, I would rather not talk about that.” Do you also give them the opportunity to say, “I would rather you did not run that?”

Anna: That’s a hard thing. Because I come from journalism and I come from where if you say something on the record, it’s on the record and that’s that. But it’s because these are very personal conversations where someone might start talking about something they didn’t anticipate talking about. You know I do try to be sensitive about that. One example is we were doing a series of interviews at a Planned Parenthood clinic in Brooklyn and talking to people who walked through the door, people who volunteered there, people who were patients. And I was talking to one woman who was a volunteer and started the conversation talking about the political reasons why she was a supporter of Planned Parenthood. As we continued talking, she started talking about the abortion that she’d had.

It’s not something that she talked about or really shared with even people she was activists with. And so at the end of that conversation I said, “You gave me your full name at the beginning of this conversation. I don’t know if you knew you were going to go there. How do you feel about using your full name?” And we just had a conversation over the next few weeks as we were getting the episode ready. She knew what was going to be in it, and she ended up choosing to use her full name and felt comfortable with that. But I felt like it was the right thing to do, to just loop back around and make sure. In the case of a famous person when that’s come up, it’s often not the famous person who has complaints, it’s the publicist who gets worried if their famous person said something provocative. And in those cases, we can usually justify how we’re using their tape and saying, “We’re doing this. We’re going to include that tape. But we’re doing it in this way and so it’s not going to come off in the way that I think you fear.” And we have that follow-up conversation. But we do try to be sensitive because when you’re asking people to come in and talk about death, sex, and money, it’s very private stuff. It’s stuff that affects other relationships sometimes,so we do try to be really sensitive to that.

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Anna: You have two objectives that are in tension with one another. You have to forge a relationship and make the person you’re talking to feel safe and make them feel like you’re not some hack who’s just asking for them to repeat the story they’ve told 16 times or ask them to talk about the thing they’ve said 16 times they don’t want to talk about. You have to take care with that dynamic, but you also have to serve your listeners. So if you listen to an interview with Paul Reubens, there was a critical juncture in his career. To skip over it or to act like it didn’t happen or to not ask the question or acknowledge it all in an interview might make the listeners feel like you dodged the hard question. I think that’s the hardest part in structuring interviews and interview questions is how do you both: protect the relationship with the person that you’re talking to and make sure you’re not wimping out and you’re serving the audience.



Jesse: Are there other things that you learned to do when you were interviewing a city council person or talking to some scientist about water safety that helped you do the kind of emotional narrative reporting that you do now?

Anna: When you’re covering a straight news story, what you’re trying to get—and particularly for radio—is someone to answer a question to you in plain language that feels sincere and that feels like it’s answering the question you have. When you’re a roving reporter on deadline, you’ve got to figure out how to have those interactions within three minutes, so you can get your tape, get back on the subway, and file before deadline. So you have to figure out, “What’s my first question? What’s my second question? What’s my third question? What’s the follow up if they don’t answer it in this way?” It’s intense listening, and it’s planning and figuring out, “What’s the tape that I’m trying to get here?” When I sit down to do a Death, Sex & Money interview, it’s the same feeling. It’s like I’m going into a chamber of intense concentration where you do the prep, you write out your list of questions that you think you’re going to ask. But then once you’re in that interaction it’s like being there in that moment and listening carefully and hearing the tape that you’re collecting and making sure it’s going somewhere. I think that, being a reporter, it was important for just figuring out how to make sure you get the tape that you set out to get, to answer the questions that your listeners are going to have.

Jesse: What do you do to prepare for an interview? Like what time do you spend and how do you spend it and what do you bring into the room?

Anna: If the person is a well-known person who’s done a lot of interviews, I do a deep dive, with the help of awesome producers who will put together preps and pull together profiles and radio interviews. I will listen to what they’ve done before, so that when I’m in the interview, if I hear them going to a place where they’re retelling a story that they’ve told before, I’ll try to kind of interject to mix it up a little bit. I try to understand someone’s body of work. I try to understand the critical moments of transition. Whether it’s when they move from place to place, or when they got married, or when they had kids, or when they decided to leave the band and go solo, et cetera. I like to have that on a timeline, like on one piece of paper, so that I can have that in the room with me and be able to look at it and say, “So when you were 30, this happened in—” or something like that. Just to place it in time, and it helps me understand, “OK if this big thing happened when they were in their mid-20s, it probably was a different emotional experience than if it happened in their mid-50s,” for example. I will go in with a timeline, and then I’ll have like, two pages of questions, so that they can both be face up to me. So I’m not rifling around with papers during the conversation. I actually don’t often look down at the list of questions that I bring in. It’s more the practice of writing them out and figuring out the beginning, middle, and end. What are the moments and interesting dynamics that we want to make sure we get to? I have a conversation with our producers ahead of time, and we all sit and we say, “What are we wondering about this person?” So we’ll have a list of questions, we’ll add different questions, and then I’ll sit with that before I go into the studio. That’s sort of a guide, but I’m not often reading questions.



Jesse: What is your objective? Like, when you step out of the booth, or wherever you’re conducting the interview, how do you judge whether you’ve done a good job or whether this one has worked out?

Anna: Sometimes I can’t tell. Sometimes I’ll walk out and I’ll think, “God. They just didn’t play ball, and that was terrible.” Then I go back and listen to the tape, and the moments where I was feeling frustrated as an interviewer actually are very revealing. That was the case when I interviewed Bill Withers. And I know you’ve interviewed him, too. But he has this way of not going somewhere that he doesn’t feel like going.

I remember coming out of that feeling like, “Oh God. I don’t know. There were so many moments when I just asked him a question he just dismissed it as a dumb way to ask a question.” But then the tape itself, showing those moments where he was kind of batting me around, was so revealing about his character and his personality. I realized listening deeper that it was just a string of pearls strung together because of the way he’s such a gifted communicator.



Jesse: So, who are your interview heroes?

Anna: I mean my first interview hero, always, has been Terry Gross. I mean that’s how I fell in love with radio, and that’s who I realized I was jealous of when I was a year out of college and knew I needed to quit my nonprofit job because I wasn’t doing what I wanted to do. And what I wanted to do was do what Terry Gross got to do. She’s my always and forever hero. I mean, you know, sentimental. It’s like laying in the back of the seat of the car with my parents listening to public radio. She taught me about pop culture and art and also how to be respectful about someone’s craft and also try to understand the personal dimension of it.



Jesse: What is the thing that you feel the least confident about, and maybe the least comfortable asking a colleague about, that you would like to know about how to do interviews?

Anna: I think what I feel the most anxiety about is becoming a cliche of yourself. I have a style in how I interact with people, whether it’s at a dinner party or in an interview, when I’m trying to make them feel comfortable or when I’m thinking [about] asking a probing question and then a follow-up question. The way that I will sort of audibly respond, like, the way I’ll say “uh huh” or the way I’ll laugh. There are certain ways that, as an interviewer, who you are is just the way that you sound on tape and the way that your show therefore sounds. And so I worry about that becoming so predictable and not an exciting experience for listeners. There’s so much in so many places to go to listen to interesting things. Like, how do you keep evolving as a journalist, and as an interviewer and as a storyteller, and the things that you think about, and the kinds of stories you tell? How do you keep mixing that up? Because in the midst of when you’re trying to keep putting out episodes—that’s a real pressure. So how do you keep finding and pushing yourself to take risks and to do new kinds of things? Because as you get better as an interviewer, you also get more predictable.

The Turnaround is available on MaximumFun.org. You can also subscribe on Apple Podcasts to get new episodes as they become available.

Photo credit: Amy Pearl

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The Editors are the staffers of the Columbia Journalism Review.