The Art of the Interview: Insights and Observations from Over 500 Conversations

Since starting what is now the Unmistakable Creative, I’ve had more than 500 recorded conversations with people from every walk of life imaginable. They’ve included bank robbers, drug dealers, best selling authors, performance psychologist, and successful entrepreneurs. Because of the sheer variety of people I’ve had the opportunity to talk to, I’ve had to learn how to adapt to each person’s story to produce an interview that is engaging, educational, and informative. These are some of my insights and observations from the last 6 years.

1. CHOOSE A GREAT SUBJECT

Choosing people to interview is as much of an art as conducting the interview. Many people assume that just because someone is famous, they’ll end up being a great interview subject. I wrote a post here on medium, about why interviewing famous people is a lousy strategy for your podcast. Famous people are interviewed ALOT, and often they’re saying the same thing over and over on each interview. That being said, if there’s one tip I could give you on interviewing famous people, it’s this. Ask them things they’ve never been asked before, dig deeper, and get closer to the bone. It’s easier said than done, but once you do, you’ll open them up for yourself and your audience.

If famous people are not the best subjects that raises the question what makes for a great interviewee? I have one filter that’s driven my guest selection choices over the years: morbid curiosity.

When your genuinely curious, you not only conduct a better interview, you end up with really interesting people to talk to .

People I’ve spoken with out of morbid curiosity

• I spoke with Joe Loya who robbed 30 banks, who I learned about through Medium. He was one of the most well read human beings I’ve ever spoken with.
• I spoke with Zoltan Istvan, a transhumanist who is running for president.

And I just tweeted Oscar Goodman, the ex-mayor of Vegas who was once an attorney for the mob. If you happen to have a connection to him, I’d love to interview him.

2. TELL GREAT STORIES

According to Kevin Roose we’re in a “golden age of podcasting.” Because of that there’s been a surge in podcast creation. A friend broke down the world of podcasting into three tiers and understanding the three tiers is important to understand the role of storytelling in each one.

Professional Podcasters

The people who we consider “professionals” are the ones whose bread and butter is their podcast. Think Marc Maron, Ira Glass, Serial, Freakonmics and The Gimlet Guys. What all these people have in common is a commitment to the craft of narrative journalism. They’re the best storytellers in podcasting and they know how to engage an audience. If you observe their work you’ll notice a few things.

Like a TV series, they tease us to keep us hooked. The end of their episodes give us a sneak peak of the following week. And if you’re new, sometimes they recap the week before. My business partner Brian Koehn clued me into this.

The production value is off the charts. It would be difficult to replicate much of what they’ve created without a skilled team. That being said, if you’re willing to become resourceful you could probably pull off some of this.

One idea that I have for a podcast that I wish somebody would do is an interview based show, but instead of interviewing a subject, interview 3 people they know (i.e, a parent, an ex gf or current one, and a best friend). Let me know if you ever plan to act on it.

Content Marketers

Content marketers, for the most part, see podcasting as a way to get their message to their customers. A large number of content marketers have an interview based podcast and many of them are starting with an existing and large fan base.

I believe content marketers have a lot to learn from professional podcasters. You can’t just take information that was once in a blog post, regurgitate it in audio form and expect that people will find it compelling. The medium has to be taken into consideration. For audio to be compelling it has to be entertaining, and informative.

The greatest challenge content marketers face as podcasters is that they (with some exceptions) don’t have a background in the craft of narrative audio journalism. They don’t come from places like NPR, WNYC, etc. There are a few that have managed to overcome this and do exceptional work.

• The Tim Ferriss Show: While don’t listen to every episode, I can see why people listen to his. I’d recommend the episode with Chris Sacca. It was the most valuable piece of audio I’ve consumed this year.
• Jonathan Fields’ Good Life Project: Jonathan is another one of those folks that is clearly committed to excellence. The production value of Good Life Project is off the charts, and he brings on a diversity of guests.

I moderated a panel on Storytelling and Creativity at Podcast Movement. Lea Thau, the creator of Strangers thought that the importance of storytelling was too obvious, but after a few days of walking aroundPodcast Movement realized how overlooked this aspect of podcasting is in content marketing.

If you’re a content marketer, don’t be afraid to steal like an artist from the professional podcasters. They have a lot to teach you.

Hobbyists

Hobbyists in my opinion are naturally entertaining and tell good stories on their podcasts because they’re passionate about their subject. They’re not getting into podcasting because it’s what the cool kids do now.

My friend Jason Cabassi runs a show called the Walking DeadCast. He’s a big fan of the show and has been working on his podcast for years. They’ve had cast members on the show, they’ve involved their audience in their episodes, and they seem to be having a lot of fun.

And there are some hobbyists who are so into what they do, they end up becoming professional podcasters.

We are naturally wired for story, and by not taking that into account, you’re missing the boat as an interviewer.

3. LISTENING

Listening is hands down the most important skill you need to have as an interviewer. It’s something that gets developed with time and practice. One of the best ways to become a better listener is not to have your questions planned in advance. And this probably sounds scary as shit. But I’ve found that not having any scripted questions forces you to be completely present. Here’s a simple framework that I’ve used

1. Ask a question
2. Listen to the Answer
3. Ask a question about the answer
4. Rinse, Wash, Repeat

Resist the temptation to fill dead air. Silence is golden. Our natural human tendency is to want to fill silence. Last summer I had the chance to interview Glenn Beck. He told me “I noticed you didn’t try to fill the pause when we hit an an awkward silence.” Experience has taught me that this can be the most powerful moment of an interview if you will just SHUT UP. Silence makes people vulnerable. Just to be clear this isn’t about manipulating people. It’s about creating a deep emotionally resonant experience for your audience. If you don’t fill the silence you’ll get people not only to open up, but tell amazing stories that they’ve never told before, the kinds that result in what NPR calls driveway moments.

And while you’re at it, read this post from Bob Lefsetz about Howard Stern’s success.

Make the Microphone Disappear

Celebrity Photographer and Offcamera Podcast host, Sam Jones says that part of his work is to make the camera disappear. Because of that he ends up having some incredible conversations with people. His is one of the few interview based podcasts I listen to on a regular basis.

Forget the microphone, forget the Skype connection, and all that other nonsense. Those are just tools. Act as if none of it is even there and just have the conversation as if you’re sitting down with this person for coffee. It sounds simple, but try it. The microphone is a fabricated barrier that exists between you and your subject. If you can make it disappear, that’s another way you’ll open up your interview subject to get pure gold out of them.

4. Research: The Double Edge Sword

There are multiple schools of thought on this.

I tend not to do a ton of research on the people that I interview. At most I’ll read their about page. In some cases I’ll read their books.

But there are people who do tons of research on their guests. From listening to Tim Ferriss, I’d guess his research on each guest is thorough.

I think you have to find a balance with just how much you want to know about your guests. The key to research is not letting it become a crutch and letting it get in the way of your spontaneity, which takes us into style.

5. STYLE

Right now the podcasting world is being lured into a somewhat seductive and profitable mimicry epidemic. A lot of shows featuring the same guests that sound exactly the same are littering iTunes. Style as an interviewer is not something that will result from some bullshit podcast in a box formula.

And the hardest thing about style is that it’s completely subjective. Some people will love it, others will hate it. Developing your style as an interviewer is a bit like finding your voice as a writer. It’s a process of self discovery that will emerge from those moments when you embrace spontaneity and try something that isn’t part of a formula designed to regurgitate the same thing over and over.

A few days ago I recorded a near 3 hour podcast with my friend and mentor Greg Hartle. It’s going to be aired in 2 parts. It’s not something that we normally do, but we had so much to talk about,we figured it would be a worthwhile experiment.

6. IT’S ALL ABOUT THE AUDIENCE

If you want to entertain an audience it’s all about them, not you- Derek Sivers

A really good interview is ultimately not about the interviewer or interviewee. It’s about the audience. One of the questions that constantly runs through my mind as I’m interviewing someone is “how will this be useful to the audience.” I want to know it will either inspire them, entertain them or cause them to change some behavior for the better.

If I feel like a conversation is not getting to one of those outcomes, I will call the interview quits in the middle of it and ask the guest for a do over. My friend Ted Ryce who shared an incredibly riveting story on the Unmistakable Creative can attest to this. After nearly 30 minutes of talking, I asked him to do a second take. Because of that he rocked the mic.

It might seem completely insane, but I’d choose doing that over a shitty interview any day. And occasionally it pisses people off, but that’s a risk I’m willing to take.

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I’m the host of The Unmistakable Creative Podcast. Subscribe to the podcast viaiTunes or Stitcher.