The Art of the Interview by Cal Fussman

At Summit at Sea last week I heard a great talk from Cal Fussman, journalist, author and Editor at Large at Esquire. Cal has interviewed top leaders and celebrities such as Mikhail Gorbachev, Robert de Niro or Al Pacino and shared with us four tips to do a great interview.

1. Aim for the heart and not the head with your first question The more important and busy the person you interview is, the fastest you have to make him feel the time you will spend with her or him will be special. The leader you are talking had hundreds of interviews already and will expect “the same boring questions on his classic topics”. Like if you interview Mikhail Gorbachev he will likely expect your first question to be on perestroika.

If you have a few minutes with him, go straight to the heart and not the head, if you get the heart you can get the head. In this case Cal’s first question to Gorbachev was “what is the best thing your father taught you?”. It caught him off guard, he immediately liked Cal who got the best of him and much more time than was expected.

2. Win before you begin

When Cal got to interview Robert de Niro, he knew de Niro hated interviews. The interview was postponed many times and when he finally got to meet him, de Niro gave Cal an excuse to not do the interview. Cal was again rescheduled and politely asked to leave but had a few seconds to tell just one thing to de Niro.

Cal answered “Oh, but I actually did not want to conduct an interview with you, I wanted to break bread”. Cal won before he began, de Niro felt safe and comfortable and took him to his favorite restaurant. Then Cal told him “I know you hate interviews if I get too close tell me and I will back off”.

If you can’t make the person you’re interviewing comfortable you are not getting the best of him.

First question de de Niro was “What was the first moment you knew you would be an actor?”, straight to the heart, back to point 1.

3. Do not stop the show

When Cal got to interview Donald Trump, Trump would not stop making long phone calls in front of him while he was seated in his office for the interview. Trump was basically showing off how important he was talking to important people on the phone, making a point to Cal.

Instead of telling him about the interview and trying to get him to do what they were supposed to do, like answering questions, Cal asked him about the talking on the phone habit! “How many hours a day do you use this phone?”.

If someone is putting on a show in front of you, do not stop the show. Listen and go right in. Let them go on and do not challenge them, they will show you who they really are. Trump gave Cal just that starting to talk forever about how he liked to… talk on the phone and who he was calling. Cal got much more making him comfortable and getting him to continue his show.

4. Ask THE question at the end

When you interview someone you generally have a key question in mind. The question you really want answered, or the question you know everyone wants the answer from.

Do not ask that question first or early in the interview it will make the person shut down. Make him comfortable first and keep it for the end. That’s what happened with Trump, once he was very comfortable with the show he put himself about talking on the phone. Earn his trust first.

useful links Cal Fussman on Wikipedia A few interviews by Cal Fussman Cal Fussman interviews Donald Trump


Entrepreneur, pilot, kite-surfer and paraglider. Subscribe to my new newsletter

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store