A couple of nights ago I was interviewing my friend Sarah Peck during a live taping of the Unmistakable Creative.  She asked me what I had learned about conducting interviews. Below I’ll dissect the entire process of how I select guests, come up with questions for interviews, and get people to open up.

Guest Selection

Start with Curiosity and Develop a Set of Criteria 

In his conversation with David Letterman, Jerry Seinfeld said a good amount of what he writes was to make himself laugh. The #1 criteria  for me is always  “am I personally curious about this person and do I think this story is interesting.” I never decide a podcast guest based on how famous or successful they are. I’ve even said no to some well-known people because of this.

When your curiosity about another person is genuine, it’s much easier to ask interesting and provocative questions. But if you’re pretending to be curious about another person because of their perceived status, your questions will always come across stilted and canned. The person I’m trying to entertain most with my interviews is me. The result of that for us is a lineup of guests that ranged from bank robbers to billionaires.

I’m also not afraid to do things that would mortify a lot of people. I’ve scrapped interviews in the middle. I’ve asked people to do second takes. And I’ve even chosen not to publish interviews that weren’t up to my standards. Occasionally I’ve had people more or less tell me to go fuck myself. I didn’t air their interviews.  The attention of our listeners is precious, and I do my best to treat it accordingly.

Landing Guests

People frequently ask me how I get people to say yes. First, let me dispel the myth that everybody says yes to me. I still get people who say no, won’t give me more than 15 minutes, or never respond to my requests for interviews. So how in the world do we find these people?

Personal Interest 

I’m always on the lookout for who might make an interesting podcast guest. If I read about someone in an article, stumble on their work through a google search, or read their book, I’ll add them to my list of ideas for people to interview. That’s how I ended up getting to talk to Joe Loya about robbing 30 banks. I also keep an editorial calendar of all of our upcoming interviews and guest ideas in Airtable.

Referrals 

When we started the podcast in 2009, I would ask each guest if there was somebody else I should interview. Josh Hanagarne led me to Kelly Diels, who led me to more people. Today I have a handful of referral sources like Sarah Peck, Clay Hebert, and Michael Roderick.

They have all not only been guests on our show but know what I look for and every single guest they have sent us has been fantastic. Anytime they refer a guest it’s almost always a hell yes.

Cold Pitches 

Occasionally I will choose a guest based on a cold pitch. But I say yes to maybe 1 out of 10 cold pitches. If you’re a publicist or you’re pitching yourself to a podcaster you don’t know, these are things that cause me to say no:

• You mention the other podcasts you’ve been on. Sometimes those podcasts are nothing like ours. In some cases, I automatically delete based on that.

• There’s no clear theme to the story

• It’s clear you know absolutely nothing about our show

• You’re a book publicist that sends a copy and paste galley letter.  Occasionally I’ve said yes to these. But it’s never because of the message. It’s only because I find the subject fascinating. I delete most of them.  I recently received what was clearly a cut and paste galley letter. At the end of the message, it said: “would you be interested in an interview with x ?” It’s quite clear to me that this is a person who is just spamming a list of podcasts with the same letter.

Some podcasters completely outsource guest selection. Given that one of the things our listeners love most is the sheer diversity of people we bring on the show, that’s something we’d never do.

Half the art of a compelling interview is selecting a compelling guest. 

Research

I’ve always considered research a double-edged sword. Too much research will make your conversations rigid and not doing enough is disrespectful to your guests. These are my basics for research

Read the About Page: When I go to someone’s about page, I’m far less concerned about their accomplishments and much more interested in who they are as a person. I always look for something that’s unusual or interesting about them because that’s often where the seeds of a great story lie. For example, Cal Fussman wrote a letter to Lyndon Johnson right after  John F Kennedy was assassinated. That experience taught him that you could connect with the most influential people in the world by asking questions.

Read their book:  I try to read the books of every person I interview. Even though I can almost always pull off a great interview without reading the book, I’ve found that reading their books leads to much more interesting questions. After reading each book, I take everything that I’ve highlighted and put it into Evernote. That way I can ask about some of my favorite passages and quotes during our conversation.

Story

One thing people overlook is that audio is an entertainment medium as much as it is an information medium. If you can entertain someone, you can keep their attention for an extended period. In a conversation with another podcaster, my friend Chris Ducker jokingly said “Srini’s interviews are like a TV Show. Even when I’m not interested, I can’t stop listening.”

Entertainment  

What makes something entertaining? Human beings are hardwired to listen to stories. Think about the experience of going to a movie. For 2 hours you suspend disbelief and get completely absorbed in a story. We can’t help but pay attention to a riveting story, and this is what often leads to what NPR calls driveway moments.

One of the reasons we start our podcast with seemingly ridiculous questions like “what social group were you a part of in high school”  is because there’s no way someone can answer that question without telling a story.  It’s a massive pattern interrupt for anyone who has done 100’s of interviews. They can’t reply with a canned answer, and it forces them to be completely engaged in the conversation they’re having with you.

• When I asked Dani Shapiro what her parents did for a living, she said: “nobody has ever asked me that before.”

• When I asked Gay Hendricks what social group he was a part of in high school, he told me a hilarious story.  He was in the chemistry lab at lunch, and three popular girls walked up to him and said “We have a friend who doesn’t have a date to the prom and we know you don’t. And we’re wondering if you’d take her.”

• When I asked Cal Fussman where he grew up, I got a history lesson, a glimpse into growing up in the 60’s, and a perspective on events like the assassinations of John F Kennedy and Martin Luther King.

You want to create as vivid a picture as possible in the mind of someone listening.

Emotion 

If you evoke an emotional response from a person telling a story, you’ll likely elicit an emotional reaction from the person listening. 

When I spoke with Alex Banyan about how the most successful people in the world launched their careers, he commented on the full range of emotions in our conversation. We covered everything from the frustration of being premed to the grit to land interviews with people like Bill Gates, to the grief of losing his father. People called his mother and sister about the interview.

Listening and Asking Questions

If you ask someone a question they’ve been asked a thousand times, they’ll give you an answer they’ve given a thousand times. There’s a good chance that they’ve answered the question “how did you get started” so many times that they’re bored to death of answering it. Once we ditched that question as the opening to our interviews, we got some of the most amazing stories out of our podcast guests.

Having a list of too many questions prepared ahead of time prevents you from listening and causes you to focus too much on your next question.  You’d never go on a date or meet up for drinks with a friend and show up with a scripted list of questions. For an interview to have a conversational tone, it has to be approached like a conversation, not an interrogation.

If you talk to a world-class interviewer like Cal Fussman, he’ll echo my sentiment above. When you don’t have a list of questions beforehand, you have no choice but to listen attentively to what someone is saying.

The question you want to ask next lies within the answer that someone is giving you.

People are like onions. They have many layers. The job of an interviewer is to keep peeling back layers, while at the same time not violating the boundaries of the interviewee.  With each layer you peel, you make a person more comfortable; you build more trust. As you do this person’s defenses, come down, and they begin to share more. You should never do this with malicious intent or to make somebody share something that paints them in a bad light. Honor their willingness to be vulnerable and make sure you do it from a place of service rather than one of seeking a provocative response from the interviewee or the audience.

Silence is Golden 

In the midst of a conversation, five seconds can seem like an eternity. But, without question, some of the most riveting dialogue that I’ve pulled out of people was preceded by a silence that felt like an eternity. Silence preceded some of my questions that resulted in the best stories.

Humans by nature need to fill a silence. And if you give them the space to do it, they’ll fill it with provocative, riveting and beautiful words that resonate. While it might be a cliche, when it comes to interviewing someone, silence is, in fact, golden, because what follows it usually is pure gold.

Setting up the Environment for an Intimate Conversation 

If you went on a first date, checked your phone constantly, responded to text messages, and replied to an email, there probably wouldn’t be a second date. A big part of creating an environment for intimate conversations with a podcast guest is eliminating distractions. Everything from your inbox to your cell phone should be shut off. If any of those things interrupt your attention, particularly if it involves a fire you need to put out, getting back into the flow of your conversation becomes difficult.

Reduce the amount of visual input, so your brain can focus entirely on the auditory information your receiving. This is one of the reasons I ask people to turn off video.  I’d also recommend recording your interviews in full-screen mode. That way the only visual input you have is Skype in full screen, and the only audio input you have is the sound of another person’s voice.

Having Evernote open is my exception to this, and I’ll usually use it in full-screen mode when talking to someone.

Even when you interview a person, you want to create an environment for an intimate conversation. Even though it’s in front of a live audience, David Letterman creates a very intimate setting for his guests.

When my friend Evan Luth interviewed me for the Offshore Insights Podcast, we recorded the interview on top of a cliff overlooking a favorite surf spot in San Diego. Given that we’re both surfers, this was a perfect setting for our chat. It ended up being one of my favorite interviews to date

Becoming a Better Interviewer

1. Reviewing Your Work 

When we started the podcast in 2009, I edited every single interview myself. And it was something I continued doing until the beginning of 2016. Many people would argue that this is inefficient and you should outsource it.  I’m convinced it’s one of the most valuable things I did to improve my skills. Because I was editing every episode, I was forced to listen to each episode a minimum of 3 times: when I conducted the interview when I was editing and after publishing the episode.

Even though I don’t edit the podcast anymore, I go back and listen to everything that I’ve recorded at least once, if not twice. When you get in the habit of reviewing your work, you’ll start to notice subtle nuances like how you transition between topics and when you use filler words. I also make a note of questions I wish I would have asked.

When I interviewed James Clear in 2014, he told me about a horrific injury in which he was hit in the face with a baseball bat. When I went back and listened, I realized  I had missed an opportunity to ask an emotional question instead of a logical one, which would have led to a better story.

By making a note of questions you wish you would have asked, you can use those questions in future interviews.

2.Discerning Feedback.  

There are people you should listen to and people you should ignore.  Sometimes we get a 1-star review for the Unmistakable Creative. When I get those reviews, my attitude is “great; our show isn’t for you.” Occasionally, one of our listeners will write in, tell me they love the show and point out something that they think would make me a better interviewer. For example, I got this email from one of our listeners:

I have been listening to your podcast for several months and I love the guests you have on show and the discussions that you have. I feel refreshed and inspired listening to it. I wanted to let you know Srini… I don’t know if you would have noticed this, but you tend to start every question with “I’m curious,” and you say it at least once, sometimes twice per question. I think you bring up awesome thought-provoking questions with your guests but also wanted to make you aware of that pattern. I know I personally like to know if there a phrase I either overuse or rely on when I speak, so I just wanted to share that with you! Love the show!

When I went back and listened to the interviews, I realized she was spot on. Until somebody points out one of your tics, you’re completely unaware of it.  Once you are aware of it, it’s all you hear. I was saying “I’m curious” so much it drove me crazy. Her feedback helped me make a conscious effort to stop doing that.

3. Listening to Other Interviewers

Listening to other interviewers is a balancing act. You want to listen to other people so you can learn what they do well, but you don’t want to listen so much that it prevents you from developing your own style. I’ve personally loved the interviews that David Letterman has done on his new show because he paints a multidimensional portrait of the people he interviews. When you listen to other interviewers, make a note of what you do and don’t like about their style.

Every interview is an opportunity to learn what you did well and what you could have done better. My first dozen interviews were with up and coming bloggers. None of them were famous. But interviewing them turned out to be an invaluable learning experience as a beginner. Don’t underestimate the value of interviewing someone just because they are not famous. It will give you an excellent opportunity to practice.

Ten years later, some of my most informative and favorite interviews are with people my audience has probably never heard of until their interview on Unmistakable Creative. Ultimately, a great interview is the result of a great story.