Maria Streshinsky is the executive editor at Wired.

“Sometimes a story comes in and it’s really lovely and well done. And you think if you just got on the phone with this person and pointed out the structure is wrong here and the chronology is wrong here, ask them to change that and send them what is known at Wired as the ‘praise sandwich letter’: how wonderful something is, how much work it will need, how wonderful it will be. … It’s not the kiss of death, it’s ‘we have a lot of work to do.’ … There are lots of pieces that come in that you’ve assigned because it’s the person with the right information with the right access, and they’re a good reporter, but maybe not a terrific wordsmith. So, you do more rewriting. Then there’s the other person that’s a really lovely, lovely writer that doesn’t have the structure and the reporting so you push on that. It’s sort of a three or four-pronged thing—it depends on the piece. I will say, somewhat controversially, there aren’t that many pieces that come in pretty clean.”

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Stephanie McCrummen is a national enterprise reporter at The Washington Post.

“I do have to psych myself up. There’s always something awkward about it and that never goes away. … No matter how long I do this job, that part of it doesn’t get any easier. It’s always a bit awkward and you’re always sort of humbled when someone actually is willing to talk to you. Then it can be kind of thrilling, once you’re in it, once you’re actually in the conversation. ... But the moment a few seconds before that is still—to this day, it’s sort of an act of will.”

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Nona Willis Aronowitz, an editor and author, writes a sex and love advice column for Teen Vogue. Her new book is Bad Sex: Truth, Pleasure, and an Unfinished Revolution.

“I'm getting a lot of emails from people saying basically ‘You've inspired me to break up with my man tomorrow.’ Or ‘I may not ever break up with my man, but I'm starting to tell the truth, at least to myself, about my relationship.’ And I think a lot of people — even though I think being open about your feelings and acceptance of all kinds of lifestyles are two tenants of modern society — I still think there's a lot of silence around dissatisfaction around sex and love.”

Anna Sale is the host of Death, Sex & Money.

“It's the result of listening, of feeling listened to, that people open up. I look like a crazy person when I do interviews, because sometimes someone will be describing something and I will close my eyes and try to picture what they’re telling me. And if I can’t picture the moment they’re describing I’ll just try to dig in a little bit more.”

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Josh Levin is the national editor at Slate. He is the host of the podcast Hang Up and Listen and the author of The Queen: The Forgotten Life Behind an American Myth.

“I think it’s a strength to make a thing, one that people might have thought was familiar, feel strange. And reminding people - in general, in life - that you don’t really know as much as you think you know. I think that carries over into any kind of storytelling.”

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Jad Abumrad is the co-creator and host of Radiolab. His latest podcast is Dolly Parton's America.

“There’s a way in which, I think, it felt more honest to be more confused in our stories. So that’s where we went.”

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Renata Adler is a journalist, critic, and novelist. Her latest collection of nonfiction is After the Tall Timber.

“Unless you're going to be fairly definite, what's the point of writing?”

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Andrea Elliott is an investigative reporter for The New York Times. Her recent book, Invisible Child: Poverty, Survival & Hope in An American City, won a Pulitzer Prize.

”I don’t see reporting as a one-way street. ... I think that people need to know as much as they can about you. And yes, there are boundaries ... but at the same time, the fact of the boundaries is something to talk about with the people you’re writing about. Isn’t it weird that this is my job to be reporting on your life when we can laugh and we can break bread together and I spend all these hours with you and you know about my kids? ... And at the same time, I’m also here to write a book. ... And those two facts I learned to just allow to coexist within me. But it was not easy.”

Renata Adler is a journalist, critic, and novelist. Her nonfiction collection is After the Tall Timber.

“Unless you're going to be fairly definite, what's the point of writing?”

Thanks to MailChimp, and Pitt Writers for sponsoring this week's episode.

Nancy Updike is a founding producer and senior editor at This American Life. Jenelle Pifer, a former Longform Podcast editor, is a senior producer at Serial. Their new three-part podcast, hosted by Updike and produced by Pifer, is We Were Three.

Updike: “I say it’s a story that’s a bit about COVID, but really about a family, and that’s the closest I’ve gotten to a short version. I don’t know. Why is that? I never have a short version of something I’m working on—never.”

Pifer: “We were doing a lot of talking about, for Nancy, what are the driving questions you tend to be attracted to? There were a few things we came up with, one of which was that you tend to gravitate toward stories where somebody is in the middle of something that they don’t know what to make of yet, and you kind of just want to sit with them and see what direction they walk in, or what they say, or what meaning they put onto something.”