The art of the interview

Asking the hard questions about asking the hard questions

I’m on deadline for a long feature, so I’ve been transcribing a lot of interviews lately. And after listening to myself fumble through tough topics and repeat myself and waste time with throwaway questions, I’ve realized I have plenty of room to improve as an interviewer. I want to get to a place where I’m not embarrassed to send the audio files to the factchecker. So I sent some pleas for help to fellow journalists and did some Googling for best practices. Here’s what I learned.

Know your subject. A recent thread on Quora posed the question, “What is the single most illuminating question I can ask someone?” Jodi Kantor, a New York Times reporter and author of a book about the Obamas, chimed in that there is no “single most illuminating question.” According to Kantor, “To ask a really high-yielding question, you need to have done your homework.”

This is especially true when you’re talking to people who are used to being interviewed. Kantor described an interview she did with the President and First Lady: “I had come to understand that equality was a serious issue in the Obama marriage, and that in the White House, the president and first lady are not treated in the same way at all. So I summoned up my nerve and asked them, ‘How do you have an equal marriage when one person is president?’” Their replies were much more illuminating than if Kantor had asked something more generic like, “What are your thoughts on gender equality?”

Come in with a plan. Max Linsky, who has the intimidating task of interviewing professional interviewers on the Longform Podcast, says, “Long interviews can have three acts — know where you want to start, where you want to end, and how you want to get there. And let the subject know the plan! These conversations can go off the rails quick — laying out the roadmap early lets you easily interrupt and move things along. Makes it feel like you’re on the same team.”

Write questions ahead of time, but prioritize conversation. There’s certain information you know you want to get, but you also want to put your sources at ease so they give you that information in an interesting way. No one wants to be interrogated. Linsky advises, “Do your research and write down tons and tons of questions. Only bring 15-20 questions to the interview. Only ask 10 of them. If you need to ask all 20, you’re not having a conversation.”

Just come out and ask the hard stuff. Maybe it’s the confrontation at the end of a long investigative project. Maybe it’s a series of personal questions for a public figure. Or maybe it’s about money or sex or something else that’s hard for normal people to discuss, let alone journalists and subjects. The hardest questions to ask are often the best. Recently Marc Ambinder argued that Howard Stern is the best celebrity interviewer because he asks blunt questions like, “What do you do with your money?” and “Who is jealous of you? Who screwed you over?” While these lines of questioning are something that guests on Stern’s show have come to expect, it’s true that he gets much more fascinating answers than your standard late-night talk show host and even some magazine journalists.

How do you work up the guts to ask such direct questions? My former colleague Amanda Hess, who writes about sex, says, “I’ve gotten better about comfortably addressing uncomfortable topics by conducting lots of interviews with people who are far more fearless and open about the subject than most people—after asking a bunch of porn stars about their first experiences watching porn, it’s become a lot easier to ask everyone else that question, too. I don’t think I’ve ever regretted asking a question, but I’ve regretted a bunch of questions I didn’t ask.”

Adds Linsky, “Also, this is kinda obvious, but I learned it the hard way: Save the personal, meaning-of-life, who-are-you-really-though, realtalk questions for the end. But ask them! People will answer!”

Embrace the silences. This is something that even radio journalists advised. Gina Delvac, who’s a public radio producer and reporter, explains, “Silence can be an asset. This is less true with newsmakers or overly practiced public speakers. But often on a personal or sensitive topic, the best moments come when you let a question float a beat too long. Dick Gordon and his team at The Story have a moment like this nearly every show. Someone hesitates, then a perfect phrase or moment of emotion crystallizes.”

Think in soundbites. This is another radio-centric tip from Delvac that can be applied to print journalism too. “Soundbites get a bad rap,” she says. “This is another way of saying, don’t get so wrapped up in a great conversation that you forget to get a really juicy quote. Once or twice, I’ve had a really lively conversation with someone, and realized afterward, I could summarize their ideas beautifully, but didn’t have that phrase that really captured the moment.”

Play dumb. Especially on deadline, you might find yourself out of your depth. Just go with it. Delvac suggests a standby radio question: “Explain it to me like I’m a (really precocious) kindergartner.”

Oh, and finally, “Keep the mic running after you finish,” Linsky says. “Listen. All the time.”

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Ann Friedman is a magazine editor who loves the internet. She lives in Los Angeles Tags: #Realtalk