4 of the Best Interviewers (and their tips)

I love listening to the best interviewers.

Larry King. Mike Wallace. Charlie Rose. Oprah. Barbara Walters.

And even better is to listen to how they do it. Their tips and techniques!

I’ve started a little list here. I’m only including interviewers who have shared their tips by video.

So far, I’ve found Larry, Mike and Charlie. Why no women? I can’t find any of them yet (giving their tips). I’ll find ’em! And I’ll find others too!

Enjoy!

Larry King – Interviewing Tips

Larry talked to host Frank Sesno at The George Washington University’s School of Media and Public Affairs on April 4th, 2010.

Here are some interviewing tips he gave:

  • The word “I” is irrelevant — “You never hear me use the word ‘I’. Because ‘I’ technically is irrelevant. It’s only ego-fulfilling”.
  • On Listening — Larry says he lives by the motto: “I never learned anything when I was talking.”
  • Be Objective/Not Argumentative– The dumbest way to begin an interview is to be argumentative. E.g. Using Osama Bin Laden as an example of a guest. Larry says “The worst first question: “Why did you plan the bombing of that building.” Instead, using Bin Laden as the example, Larry recommended (off the cuff) this question “Why did you leave the riches of Saudia Arabia from one of the richest families to live in the hills.” (now “he knows I’m interested in him…I’m objective”)

Werner Erhard Interviews Mike Wallace on The Art of an Interview

Source: https://wernererhardvideo.com/werner-erhard-interviews-60-minutes-mike-wallace-on-the-art-of-an-interview/

I love finding videos like this.

Here’s Werner Erhard (author and lecturer known for founding est Training) interviewing Mike Wallace (arguably the best interviewer from the “60 Minutes” show).

Here’s what Wallace shared on his approach to interviewing:

On Research & Preparation

“I’ll start out with a legal pad…and start writing questions…everything that comes to mind. What I’ll do is get maybe thirty, forty, fifty clips about an individual. And just write questions.

Then I begin to find a kind of form. I want to talk about money to that person, I want to talk about power to that person, I want to talk about disappointment (to that peson)….

And little by little you cull the chaffe and keep the wheat and I’ll wind up generally speaking with 50 questions in six or eight categories .

By that time I’ve learned enough about that indivisual so that I’ll feel comfortable, no matter what direction he or she takes me, I can just put the questions aside and say ‘ok, let’s talk about that”.

On Interviewers Ad-Libbing

“The business of the ad lib interviewer is vastly overated. I’ve never seen a good interviewer who really ad libs.”

Put the Interviewee at Ease

Wallace gave the story of trying to get General Noriega to agree to be interviewed.

Wallace told Noriega privately that he used to have the same type of acne problem that Noriega had…and that Mike’s cameraman is the best in the business and will make Noriega look great.

Noriega agreed to the interview and it went down as a famous interview (here’s the only version of the whole interview I could find (sorry for the crappy quality)).

Charlie Rose Shares Interview Tips at Yale

Charlie’s “Rules”

Charlie (around the 13 min. mark) rattled off some rules he has. I’m listing a few of my favorites here:

  • Psychology of the individual is so crucial. To understand where they are coming from…why they are there and what they want to express…”
  • Preparation. “There is joy in preparation. There is joy in learning everything you can”.
  • Listening. He quotes his colleague Diane Sawyer as saying interviewing is “like tennis and the most important interviewing technique is you listen in the way an athlete waits for the ball — are you ready to move in this direction, are you ready to move in that direction?” “You listen without self-consciousness and you listen without self-importance. You listen as a human being first and you listen as a pursuer of the facts second and you never listen as a television personality.”
  • Seize the Moment. “An interview, like a sporting event, may go off in any direction you never imagined and you have to hear that moment and you have to seize it…and you are able to do that because you have prepared
  • Engage. You need to do that so”You’re taking that person to somewhere they haven’t been”
  • Spontaneity. “There has to be always if it’s going to be good: spontaneity”

Charlie’s “Fallback Plan” to Interview ” on Interview Questions

Charlie, at about the 17:23 mark, says he uses the “Proust questions” as his “fallback plan…when all else [in his interview] fails”. Here are some of Charlie’s favorite Proust questions:

  • What is your self-image?
  • What are your obsessions?
  • What are your earliest memories?
  • What are your greatest achievements?
  • What are your cherished moments?
  • What are your dark moments?
  • What is your favorite book, movie, painting?
  • What have been the critical turns in your life?
  • If you’re in trouble, who do you call?
  • If you didn’t do this, what would you do?
  • Who would you like to meet?
  • What would you like to change about your life?

A bonus tip Charlie shared early on is this tip from investigative reporter Bob Woodward:

“…[Bob Woodward] has this amazing technique in which if there are five people in the room, he’ll get to one… and that person will tell and then go to the other person and say “I already know” and that person will [think] ‘Well, since he already knows, I’ll tell him everything. And by the end of five of those, he does have the story.”

Sean Evans (Hot Ones)

Sean Evans’ interview with Jake Gyllenhaal showcases the most techniques of Sean’s mastery of interview questions.

Interview Tips from Sean Evans via Jake Gyllenhaal Interview:

  • Prepare thoroughly:
    Sean Evans impressed Gyllenhaal by asking about his work in the little-known play “This Is Our Youth,” catching him off guard with specific insights, and referencing moments from Gyllenhaal’s early theater days rarely mentioned elsewhere.
  • Ask purposeful, personal questions:
    Evans invited Gyllenhaal to reflect on his move from heavy dramatic roles to comedic performances in films like “Okja,” leading to Gyllenhaal sharing how comedy revitalized his approach to acting and challenged his comfort zone.
  • Listen actively and adapt:
    During the interview, when Gyllenhaal got animated talking about his experience training for “Nightcrawler,” Evans picked up on this excitement and asked deeper follow-ups about his preparation and the toll it took, rather than sticking rigidly to the lineup.
  • Build rapport by sharing a challenge or common ground:
    Evans laughed and powered through the escalating hot sauce challenge alongside Gyllenhaal, with both commiserating over the heat and joking together, which broke down the usual interviewer/guest dynamic and made the atmosphere more relaxed.
  • Craft a narrative and stay composed:
    As the wings got hotter, Evans tied Gyllenhaal’s stories from his childhood, his adventurous spirit, and career risk-taking into a cohesive arc, all while keeping the conversation on track even as the spice levels became overwhelming.
  • Show genuine enthusiasm and visible effort:
    Evans referenced lesser-known projects and specific lines from Gyllenhaal’s films, like recalling particular scenes from “Enemy” and “Donnie Darko,” which demonstrated a deep engagement that Gyllenhaal acknowledged and appreciated.

Thanks for reading!

Rob Kelly, Chief Maniac of Daily Doc

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