A Guide to Interviewing

Joshua Mohr has a new novel coming out and Jon Reiss is preparing to interview him.
As a freelance writer one of my favorite work-related activities has been interviewing writers, musicians and actors.  I’ve been fortunate enough to conducted interviews of all stripes: firing off questions at Fred Armisen on a red carpet, having a laid back phone conversation with Bad Brains, trying to get a quick quote out Nick Zinner from the Yeah Yeah Yeahs at a party and having him tell me to basically go and do dirty things to myself.

My favorite type of interview is a one-on-one extended interview with an author. One of my first freelance assignments was to interview Sam Lipsyte, author of Homeland and The Ask. Lipsyte was the apotheosis of the kind of writer I aspired to be–smart, witty, quick, while also dry, sarcastic and slightly nihilistic.  I was a nervous mess.  However, I learned some important lessons in that interview.

I was so nervous that I’d written five pages worth of questions, all meticulously worded and arranged. I’d read everything there was to know about the guy beforehand. So it didn’t end up mattering that I completely blew my plan for the interview.  I asked the first question on my list and none of the others. I said oddly forthcoming things that I was embarrassed to hear myself say when playing back the recording for transcription. I just talked to the guy.  Did I come off like the wet behind the ears fan that I was? Absolutely.  Nonetheless, I’m proud of the interview to this day because I was prepared, and also because I followed the most important rule of interviewing: listen.

As I write this column, I’m preparing for an interview with author Joshua Mohr, who is to me now what Lipsyte was to me then–writer whose control over his craft is seemingly endless, yet who maintains the kind of dark wit that has always drawn me to fiction.  Preparing for this interview after being on an interviewing hiatus, I re-acquainted myself with the rules of the game.

Know What Kind of a Piece You’re Writing
This is pretty obvious, but it’s important to know what the format of your piece going in.  For feature  pieces about a single person, (rather than a multi-sourced investigative or news article) there are essentially two structures to follow, a narrative or a Q & A.  In the former you have much more control as a storyteller.  Getting and finding great quotes is a major discipline and it comes partially from experience and mostly from hard work.  In this kind of piece, more of the work comes after the interview, in the crafting of the piece, whether that means interviewing more people, or delving deeper into research.

In the Q & A format you’re resting your piece on the strength of your interview, so your questions, the order you ask them in, their length and the subject’s answers all matter a lot. This isn’t just a conversation, it’s a conversation you’re shaping at all times. I’ve always enjoyed the authenticity of this type of interview.  The greatest thing you can hope to achieve in Q & A is to get to the personal and philosophical core of your subject.  If your subject starts talking about the meaning of life, the true nature of the music they play or the art they make, you’ve gotten to something.  In 1966, Playboy/Village Voice writer Nat Hentoff interviewed Bob Dylan for an issue of Playboy, wherein Dylan philosophized about the music he did and didn’t make.  To get this, Hentoff did what so many of the people who had interviewed Dylan before him failed to do.  If you watch the documentary Don’t Look Back, reporters often treated Dylan like a monkey in a cage, who if poked enough would put on a spectacle.  They threw his past off-the-wall quotes in his face rather than asking with interest, what he meant by the things he’d said.  Hentoff looked at everything Dylan had said and done, both from the point of view of an artist himself, as a fan, and as an observer and asked his questions accordingly.  Of course, he also followed this next very important “interviewing must.”

Read Everything By and About Your Subject
If you’re interviewing Bob Dylan, you’d better have read Chronicles (his memoir) within a few weeks of the interview.  You’d better have listened to Dylan whenever possible leading up to the interview. You immerse yourself in the person’s work because it’s the only way to come close to what it’s like to be in that person’s head.  Also, it’s my opinion that it’s okay to approach an interview as a fan as long as you can still be objective.  Some reporters are known to be combative with their subjects, and I don’t think these reporters always get the best interviews. That being said, don’t be afraid to ask tough questions–just think carefully about how to ask them to actually get a real answer. This can be difficult in an age where everyone in entertainment seems to have a team of publicists, but it’s your job.

Also, assuming you’re not writing the first ever interview with your subject, you should have read every other interview with them in existence.  So often writers fail seize on opportunities to ask great follow-up questions.  If you notice this in a past interview, seize it, quote your subject and ask them what they meant by their answer.

Stay Somewhat Current
Writers, musicians, actors, usually want to talk about their most current work.  Of course, if you’re talking to Vanilla Ice about his new novel (doesn’t exist) there’s the tendency to want to ask him about “Ice, Ice Baby,” and that’s not wrong, but it’s a give and take.  The subject doesn’t have control over what you put in your piece but they can end an interview if they don’t like your questions.  It’s always a trade off between what you want to know and what they want to talk about, and this is more prevalent the more famous they are. Start with their current project and then say, “You know, In thing I always wondered about ‘Ice, Ice Baby’ was…”

However, there is something is else to consider here.  People often have the most interesting insights on their recent work.  In the book, Eating The Dinosaur Chuck Klosterman examines the nature of interviewing by talking with some of the best in the business. Ira Glass offers Klosterman the insight that people are often most articulate about the things that they’re still working through in their minds.  This is true, not just because these things are at the forefront of their minds but because these thoughts haven’t been put through the filter of time and good judgment.  I recommend Eating The Dinosaur for all aspiring interviewers as an inspirational and instructional tool.

Be Personal
I often find myself worrying about whether I’m talking too much in an interview. Usually, you should not be afraid to talk.  The closer you can come to turning your interview into a conversation, the better, and often this means contributing.  You shouldn’t be talking more than your subject, but don’t be afraid of a back-and-forth.

Have a System
You have to use a recorder when you interview someone. You just do. Yes, Truman Capote claimed that he remembered every word of every interview he did, without taking notes. You are not Truman Capote. Bring a notebook (or type on your computer or tablet) for notes, making sure to carefully write down quotes that you recognize as being great. You can also look at your recorder and note the time on the track when your subject launches into a particularly juicy bit that you know you’ll want to include, for your own reference during transcription. Also, it puts the subject’s mind at east to see that you are dedicated to taking down their words with accuracy, and, sometimes while you’re scribbling away and they have a moment to reflect on what they just said, they’ll say something even more amazing. This is true for post-interview small talk, as well, if you’re in person. Don’t turn that recorder off until you say goodbye, because sometimes you’ll get something great after the formal part is done and you’re putting your notebook in your bag.

Don’t Get Discouraged
Often it can feel like an interview is not going well, yet you realize in the editing process that it was a great interview.  On the other hand, an interview may feel like it went well, your subject seemed calm, content, you got along with the person and yet, the interview doesn’t read as very interesting.

Luckily, when you’re writing a print interview, it’s amazing the difference editing can make.  I’ve had interviews that I walked away from, frustrated and annoyed, that were absolutely compelling on the page.  The truth is, you really don’t know until it’s transcribed.

Interviewing can be one of the most enjoyable aspects of freelance writing. My final piece of advice is to pay attention to the people who do it well.  Not just in print, but on TV and radio as well. Watch what these people do, and mimic. If every interviewer out there listened to a little more This American Life, there wouldn’t be enough room on the Internet for all the great content that would come forth.

Scratch that, there’s always room on the internet.

For more of my freelance blunders that turn out all right in the end, like the TV sitcom I try to imagine my life to be, follow me on Twitter and check out my blog.