How To Become A Great Interviewer (Part 1)

A collection of pro tips shared from pro interviewers.

The Turnaround is a new podcast by Jesse Thorn where he interviews interviewers. Three episodes in, it’s already one of my favorite new podcasts to listen to. Having just started my own interview podcast, I listen to The Turnaround with the intent to learn from some of the best and most experienced interviewers.

Below is a summary of my favorite pro tips as shared by the first three guests on The Turnaround: Susan Orlean, Ira Glass, and Marc Maron.

Susan Orlean

Susan Orlean is a staff writer of The New Yorker and host of the Crybabies podcast.

Rather than entering a conversation from the perspective of a journalist who has a series of questions, Susan Orlean approaches each interview with the goal to have her guests teach her about what it is that they have mastered over time.

Susan is both a writer and a broadcaster and there is a difference in the role she plays depending on the context. In her role as a writer she is the story teller and as a broadcaster it’s not her but her guest who is the story teller. Her role then as a broadcaster is to guide her guest through their own story instead of telling it for them.

What was surprising to me was to learn that Susan never prepares questions in advance. She walks into a conversation or interview with curiosity rather than preparation. She trusts that the guest knows their story best and she focuses on getting them to share it without a preconceived notion.

“Most of the stories that I do end up not being at all what I thought they are going to be. I take that as a good sign. I go into it thinking–well, I am going to find out about X, and actually, if I’m really open, and really listening, and really paying attention, the real story emerges. The one that I couldn’t have anticipated. And that’s what I’m following.”

The crucial skill to be successful with this approach is to be a fast thinker:

“Being good at thinking on your feet is essential, because you’re diving into something you don’t know what you’ll encounter.”

On the question whether or not she uses quotes verbatim, she replies, passionately:

“Oh yeah, oh yeah! I cannot state strongly enough that is utterly totally unethical. It’s a lie. If you put a line in quotation marks and attribute to someone something they actually didn’t say, it’s a lie. It’s an absolute lie. If you didn’t quite get all the words of the quote down, then paraphrase it. If you feel sure you know the intent of what they said, but the quote isn’t–you didn’t get the words down, paraphrase it. I feel strongly about it.”

Her secret pro tip to interviewing that all interviewers should master: listening.

“Be a listener. Be a good listener. And sit with your discomfort, which is part of what listening requires. Those long silences, the moments where you aren’t exactly sure what you’re doing or a person is not responding right away. It’s not easy but you have to learn to live with that and listen and be in the moment.”

Ira Glass

Ira Glass is a public radio personality and the host and producer of This American Life.

Almost exactly the opposite approach to Susan, Ira Glass is always prepared. He always creates a coherent plan about what to ask in each interview, so that he can later narrate the story from point a to b.

He calls this “pods”, a series of actions in a story that lead from one part of the story to the next. This creates what he calls a “narrative suspense” — or a forward motion of ideas which leads people to want to listen to what’s next, a powerful tool for journalism.

A technique he uses to receive affirmation for what he heard is to play back to the interviewee what he thinks their story means. This can often can lead to a new set of insights, or bring to light a correction.

Ira is surprisingly open about his vulnerability of walking into an interview nervous. He is often nervous before an interview with a famous person because he fears that this person will judge him. He also is often nervous because he is not sure how someone will react to his questions. He works hard to be and stay relaxed in those situations.

Ira talks a lot about using empathy as an instrument to get inside of a person’s head in order to find and frame a question.

The one thing he asks people most often is to ask for an example, a powerful technique to move from a theoretical idea to a practical insight.

“Never loose an opportunity to ask for an example.”

In addition to asking how someone thought something would play out, he follows up by asking how it actually did play out. Inside of that answer is the story that might have never been shared before.

Marc Maron

Marc Maron is the host of WTF With Marc Maron and has interviewed more than 800 people for this podcast.

At the core of what Marc Maron does is to create connection. He records all his interviews at his house (the garage, actually!) and starts by making people comfortable. His goal is to place people into a “come over and hang out” setting. He makes coffee or tea and starts conversing. He starts recording but doesn’t tell people.

In addition to connection, his goal is to get the tone of the conversation into something organic and authentic. To do that, in addition to asking about the craft and process, he looks for something emotionally revealing.

He says that having prepared questions in an interview can be a limiting factor and that having an idea about the backstory, and then to go there, leads to the best results.

He works with his producer to ensure that he never looses sight of the big picture or ark of where the conversation needs to go.

Come back for Part 2 after the next 3 episodes of The Turnaround.

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