The Austin Chronicle describes his interview skills as “peerless.” Tim Ferriss calls him a “Verbal Jedi.” Countless others say he’s “transformed oral history into art form,” conducting hundreds of probing interviews with the world’s most compelling, influential and iconic people, including Mikhail Gorbachev, Jeff Bezos, Richard Branson, Jack Welch, Jimmy Carter, and Muhammad Ali.
As a New York Times bestselling author and the literary genius behind Esquire Magazine’s What I’ve Learned Column, Cal Fussman has learned a thing or two about the power of asking good questions.
Good questions can lead to greater understanding. They can strengthen relationships and elevate leadership. They can even get you to the most powerful person on the planet, something Fussman learned at just seven years old after sending one in a letter to the President of the United States (and receiving a reply).
In this episode of Project Luminary with Kristen Aldridge, learn how Fussman is inspiring organizations to take a new look at their business through storytelling, connection, and the fundamental idea that changing your questions can change your life.
The Austin Chronicle describes your interviewing skills as “peerless.” Tim Ferriss calls you a “Verbal Jedi.” Your accomplishments are truly nothing short of iconic, and one of the many remarkable things I’ve learned from you is to always aim for the heart first with our questions. So when did you realize that asking questions was a natural fit for you?
Cal Fussman: That’s a really good question, and it’s the story that really gets to the essence of my journey. It goes back to November, 1963. I’m in the second grade, and I’m sitting in the middle of the classroom, when Miss Jaffy walks out the door. She comes back in a few minutes later, and she is just pale. She tells us that President Kennedy has just been shot, and we’re all let out of school, we go home, and Lyndon B. Johnson is sworn in as the new president. I’m sitting at this kitchen table and I’m just trying to grasp what’s happening. And I’m thinking to myself, “This guy, Lyndon B. Johnson… I bet he wanted to be president. Does that make him happy? Or is he sad, because he’s only president because Kennedy’s been assassinated? Or maybe he’s scared that they’re going to try to kill him to!”
So I pick up a piece of paper and I write, “Dear President Johnson, what does it feel like?” And I start to ask him if he’s happy, or if he’s sad, or if he’s scared. It’s not a long letter, but I wish him well. Six months later, my mom comes racing up the steps to the apartment, and she’s got this letter from the President. It was amazing for a few reasons. One, it was written by the his personal secretary, but there was a misspelling in it. Which basically told me that this letter was just sent for you. And on top of that, it treated me with respect. Like I was an adult. The second sentence (on the letter) is what I will always remember. “An answer to your query”. And I had no idea what a query was! It made the smallest kid in a second grade class feel like a very big man. Now everybody’s over at the apartment to see the letter. I’m asked to go see the principal, he wants to see the letter. In that moment, I knew that a simple question could get you to the most powerful person in the planet. And it basically put me on the course for the rest of my life.
When you got a little older, you traveled for 10 straight years. And you’ve said that these travels have helped you become a better interviewer. So how did traveling the world help shape your approach to an interview?
Cal Fussman: Well, one of the reasons is because I didn’t have very much money when I was traveling and so I had no money to go to hotel to hotel to hotel to hotel. I needed people to take me in. I needed them to invite me into their homes. So I basically took the task of getting on buses and trains and walking down the aisle and looking for an empty seat next to somebody who looked interesting. Somebody who I thought I could trust. I did that way more than hitchhiking. Although, I tried hitchhiking a few times and people picked me up and we’d start talking and then they would take me home. But a lot of times just being at the railroad station, waiting at the tracks, you start talking to somebody and it would lead you to their home.
So these experiences of finding people who I could trust and making them want to include me in their life, that skill or that spirit went with me when I started to interview some of the most talented, powerful and compelling people on the planet for Esquire Magazine. So when I was walking in to interviews with Al Pacino or Richard Branson, I would go in completely relaxed as if I was walking down the aisle of a bus or a train. And not feeling like a journalist with a tight tie on that had to ask just the right questions. It made people feel comfortable, and I would do other things too. I remember I brought my six year old son into an interview with Jimmy Carter. And after a few minutes, it got boring to him and he’s watching this mosquito floating around my head and he goes up and whacks me. President Carter thought that was the funniest thing. And then the President starts talking about his grandkids, and his relationship with them. And it’s that humanizing quality that I find gets the most out of an interview, as opposed to “Alright, what question am I gonna nail him with.” I never go in thinking like that.
Over your career, you really have interviewed some of the most influential and interesting people on the planet. Who would you say was your most challenging interview, and what did you learn from it?
Cal Fussman: I was interviewing the famous defense attorney, F. Lee Bailey, he was famous in the O.J. Simpson trial, and he said to me, “OK, look, you got two hours. Once these two hours are up, I’m going to my case, and you’re not going to be able to get ahold of me.” This was my first Esquire magazine “What I’ve Learned” interview, and I went out and bought a new tape recorder. I put the recorder down, sometimes it’s rolling when he’s talking, but I keep seeing it stopping and starting, stopping and starting, and I’m nervous. The interview ends, and I want to listen immediately, because I know something’s up. And that’s when I can hear that half of his answers are cut off. From that day on, I was always prepared with two recorders, and it’s really a great lesson in preparation. And so, what I found were so many of the things that I learned in interviewing, work in all these other professions.
A big part of what you’re doing now is helping organizations ask better questions to get better results. So in terms of hiring someone new, what are some of the questions we should be asking to make sure that person is the right fit?
Cal Fussman: You’ve got to wonder, “Who are my applicants?” There is a lot of thought that should be going into this process, as opposed to, “Here’s the job!” and, “Where did you go to school?” Because once you do that, your missions is, “OK, how am I going to weed people out? Let me see if I can get this person out of here on the first question.” There’s an expression in hiring, “You get hired for what you’ve done, and you get fired for who you are.” There are ways of finding out about people and getting to their essence. And my feeling is, if you just overlapped the preparation that I went into to interview Mikhail Gorbachev or Robert De Niro, and applied it to interviewing, you’re going to get to the bottom of these people.
Not only should we be asking better questions to others, as leaders, we should also be asking better questions to ourselves. So for all the leaders out there, what questions should they be asking themselves every single day?
Cal Fussman: You should be looking at the things you want to change. I’ll give you a classic example. So I’m giving a speech, and then the president of a company came up and said to me, “You know, I would love to speak, but I can’t do it. I can’t get in front of people.” And I said, “Well, what if you changed your questions? Could you speak in front of a mirror? Could you speak in front of a mirror until you memorized what you wanted to speak? After you had completely memorized this, could you walk out in front of a group of people and just pretend you’re looking in the mirror?” I got an email from her about a month and a half later saying, “You wouldn’t believe it! I got in front of the mirror, I practiced, I went in front of a group… They loved it! They want to have me back!” Here, with only three questions, we were able to change the way she looked at it. You can do that with any problem. So when somebody tells me that they have a problem with a certain thing, I’m convinced that just by having them change their questions, they can start on a journey to solve the problem.
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