Frank Deford, the exceptional Sports Illustrated feature writer, once observed that interviewing is “two people on a high school date, and it’s not just the reporter doing the flirting.”
Like high school, Deford’s advice is fraught with hidden complications. I could spend a series of columns detailing how to conduct a proper interview. It takes a long time to become halfway competent, because there is always more to learn. That is why I talked to Will Harris, who regularly interviews celebrities for high-profile outlets such as The A.V. Club and Vulture.
Harris, who is terrific at his job, said a good interview is based on silence. He used this Roger Ebert line as an illustration: “…My best technique has been to listen. This turns out to have been a useful strategy, because when you allow people to keep on talking, they are likely to say anything.”
I asked Harris how he keeps himself from talking. He said the proof is in the product. That’s your first tip: You’re not the star; shut the hell up.
Here are more to get you started.
Start with positivity.
In 2014, I interviewed actor Michael Cera, then starring in This Is Our Youth on Broadway. The interview was beyond dreadful; the transcript actually ended with me saying, “Ugh.”
I sent the skimpy, paint-by-numbers Q&A, along with the transcript, to my editor at Broadway.com. “Next time,” she replied, “say that you enjoyed the play.”
Now, I can’t say that to a dentist or an attorney when I’m doing an interview for an advertorial. But I can thank them for taking the time to talk to me. I can tell an author I enjoyed their book. These are not lies. I am appreciative to anyone who sets aside 10 minutes to speak to me—nobody owes me anything. Plus, if I’m interviewing someone in the arts, it’s because I am a fan of their work. I think Michael Cera is a fine comedic actor. I loved the revival of This Is Our Youth. We didn’t hit it off. It happens.
Sometimes an interview bombs.
Everyone has their horror stories. It’s not always your fault. The source has to leave before you develop a rapport. She has a busy day and considers this interview a major inconvenience, even though you scheduled the talk a week ago. He’s sick, drowsy on OTC cold medication, and would rather be in bed. Your voice reminds them of their ex, the one they really hated. People are fickle. An interview isn’t an emotional vacuum.
Skip the background information.
I read a Q&A recently where the first question was a basic one about the subject’s company. I cringed. That can be answered by a visit to the company’s website and provided as context in the introduction. These “fill me in” questions are a waste of time that insults the source: You care so little that you couldn’t bother to learn basic information about them. That’s a good first step – off a cliff.
Don’t wing it.
“Well, I’m having a conversation. My personality will get me through this,” a newbie might think. Nope. Personality is a sidekick to preparation, not the hero. You may have a handshake like a warm glove and a smile that makes every grandma’s day, but those mean nothing if you don’t know where your source teaches. Or what she teaches. Or if she’s a teacher. Maybe she’s a preacher. Where did that email go?
Five years ago, I interviewed actors Cobie Smulders and Guy Pearce for The A.V. Club about their movie, Results. I watched it. I watched the director’s previous film. I watched a few of Smulders’ and Pearce’s recent movies, a real sacrifice because Delivery Man is awful. Did I need to do all that? No, but that knowledge made me comfortable. I think that made them comfortable, which led to a wonderful, wide-ranging 20-minute chat.
Many of us grew up with television news. There were two models during my den-bound childhood for interviewers: the Barbara Walters soft-focus living room chat or the 60 Minutes “answer the question, sir” interrogation. I fall into neither category. So I decided to ask a question, be quiet, and occasionally offer a relevant observation to move things in a promising direction. You have to find the comfort level where preparation meets sincerity.
Do not ask questions that can be answered with “yes” or “no.”
Those are dead-ends. You want people to talk, not justification to clam up. Are we clear?
Ask for more.
“Gee, I don’t understand how competitive hot dog eating works. I’d love to hear an explanation.” “You said you spent a summer tap dancing with Shirley Temple on the U.S.S. Intrepid during the Vietnam War. What was that like?” Those answers not only lead to clarity that enhances your story, but they show the source you want to get their story right.
Have questions ready, but feel free to stray.
Don’t worry: Harris also does this. I interviewed Tommy Chong (of Cheech & Chong) a few months back for the website InsideHook. I had questions written out, but the comedian was so eloquent that I let him go. He discussed politics and god and aging. He was amazing because he cast aside the pot-smoking persona most people know. The real person emerged.
If I’m writing a reported piece with multiple sources, I always ask my interview subject two final questions: “What else would you like to add?” and “Who else can I talk to?”
This article is not where the education – mine and yours – ends. Resources are everywhere. Jancee Dunn’s But Enough About Me, which covers her years as a reporter at Rolling Stone, is chock full of tips. Every interview Max Linsky does on the Longform Podcast is a masterclass of casual preparedness. Late journalist Oriana Fallaci and NPR’s Terry Gross have compilations. Dig up Scott Raab’s old interviews at Esquire.
Steal from people who know more than you until the police bang on the door. When they do, you can forego the open-ended question.
—Veteran freelance writer Pete Croatto (Twitter: @PeteCroatto) has written for The New York Times, Columbia Journalism Review, Publishers Weekly, The Christian Science Monitor, and many other outlets. His first book, From Hang Time to Prime Time: Business, Entertainment, and the Birth of the Modern-Day NBA, will be released by Atria Books on November 17. He lives with his family just outside of Ithaca, New York.