Big Questions with Cal Fussman

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TSP 194 | Big Questions

Episode Summary:

Podcaster, in-demand speaker, writer, and expert at asking the best questions, Cal Fussman believes that a good question could get you to the most powerful person on earth. Sharing a story that is not short of that, he takes us into the time where he landed an interview with Mikhail Gorbachev and how he managed to extend their conversation beyond what was allotted for. He then transitions to the power of asking the right questions, one that strikes at the heart. Equally important as well is the ability to listen, and Cal shares how it can ultimately improve your relationships with people. He shares the three things that a question is part of what allows for a successful pitch to happen while also giving us a look into his experience of being the sommelier at Windows on the World at the top of the World Trade Center.

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Big Questions with Cal Fussman

Our guest is Cal Fussman who is an expert on asking questions. Cal says the questions have guided his life ever since he was seven years old and he sent one to the president of the US and he got a reply. The key is how do you ask a question that gets you an answer that’s useful and unique? Cal is somebody who has a podcast himself called Big Questions. He’s an in-demand speaker for huge companies around the world talking about the power of questions. Magazine lovers may recognize Cal as the writer who spent a week with Muhammad Ali for Esquire magazine’s cover story. He’s interviewed everyone from Mikhail Gorbachev to Jeff Bezos, Richard Branson, De Niro and hundreds of others who have shaped the last 50 years. Wine lovers know him as the sommelier at Windows on the World at the top of the World Center before it was taken down on 9/11. Before that, he’s won a James Beard medal. Cal, welcome to the show.

Thank you. That was quite a pitch.

It’s easy to do with someone like you who has such a rich background in journalism and you have breakfast with Larry King every day. You’ve got a family life going on. You’re consulting for companies on how to improve their sales through listening and storytelling and the power of questions. The first question I want to ask you is about your own story of the origin. You can go back as far as you want because people are always interested. Cal was not always a journalist. Questions have been a big part of your life since you were seven. Let’s start with that story as kicking off place.

A good question can get you to the most powerful people. Click To Tweet

It goes back to a very specific day at the end of November 1963. I’m in second grade. Right in the middle of the class, I’m the shortest guy in the room and Miss Jaffe leaves the classroom for a moment. She returns completely different wearing the same clothes but everything about her was different. She was pale and she started to speak in a voice that was so overly calm, it was scary. She tells us that President Kennedy has just been shot. It’s a Friday afternoon. Everybody is let out of school. We all run home to turn on the television and see Walter Cronkite the CBS broadcaster who everybody looked upon as the person who could give them the truth. Very different days than we have where everything is segmented and people turn in to hear the one voice that they’re looking for. Back then, it was this guy telling us the truth. He tells us that President Kennedy has been assassinated in Dallas. That set the whole nation into a busy state.

My dad when he got home talked to my mom and they realized it was the first time in my life that I was confronting death. I was seven years old the week before. They called me over to the kitchen table and they explained, “Cal, you’ve been watching the news and you know what’s happening. We’re here to tell you that this has happened in our country’s history before. The country has a plan in place to deal with it.” That’s as you now know Lyndon B. Johnson, the Vice President, has stepped up and assumed the presidency. “We want you to know when you go to bed tonight, everything’s going to be fine. When you wake up tomorrow, you’re going to have breakfast just like you did. You’ll go out and play just like you did so you can get a good night’s sleep.” I’m sitting at the table and I’m thinking, “This guy Lyndon B. Johnson the new President, I’ll bet you he wanted to be the president and now he is. Is he happy to be the president? Is he sad to be the president because he’s only the president because John F. Kennedy was assassinated? Then I think maybe he’s scared to be the president because they may try and kill him too.”

I’ve got these thoughts rolling around my head and I can’t figure out what Lyndon B. Johnson is feeling. Is he happy? Is he sad? Is he scared? Are there other emotions? I picked up a pencil and a piece of paper and I started writing, “Dear, President Johnson. How does it feel?” I asked him if he was happy, sad or scared or all the emotions and I wished him well. I had just been taught how to officially write a letter, so I was able to drop it in an envelope put my address in the top left-hand corner, lick a stamp, put it in the top right-hand corner and I’d put President Lyndon B. Johnson, the White House. I didn’t tell anybody about this. It’s not like there was any ambition in this letter. I wasn’t thinking of being Secretary of States. I just wanted to know what this guy was thinking so I didn’t tell anybody. The next day I took it outside with me to play dropped it in a mailbox and my parents were halfway right. The things did not return to normal. The next day the suspect in that shooting, Lee Harvey Oswald, was shot in the police station by a nightclub owner named Jack Ruby and then there was the President’s funeral.

TSP 194 | Big Questions

Big Questions: A great storyteller pulls us into the situation where we feel like we’re there.


I still have vivid memories of John-John, the three-year-old son of the president saluting as the coffin passed him. It was John-John’s birthday. Life didn’t return to normal so quickly but after a time it did. I forgot about the letter until about six months later, my mom comes racing up the steps of the apartment holding this envelope in her right hand. The letter was addressed to me from the White House. It was the president through his personal secretary, Juanita D. Roberts, answering my questions. What was very cool about it was the way it was written because it was not written down to a second grader. It was written with great respect and I knew that when I reached the second sentence started, “In answer to your query.” I had no idea what a query was. The thing about it was the apartment filled up with people. Everybody wanted to hold the letter from the president and the principal at the school wanted to see the letter. When I went back to school, suddenly the shortest guy in his class was a very big man. The lesson that I took out of that was that a good question could get you to the most powerful person on Earth. It would guide me for the rest of my life and get me to many of the most powerful people, from Nelson Mandela to presidents like Jimmy Carter. I interviewed Donald Trump. You mentioned some of the actors like De Niro and Pacino that I’ve spoken with. It all started on that one day.

The thing that resonates if you are looking for tips on not just how to ask a great question but storytelling in general as part of a good pitch is you paint a picture so vividly. The year, the name of your teacher. She looks different even though she didn’t change clothes. You pull us into the situation where we feel like we’re there and that’s what a great storyteller like you does. The thing that resonates with me is you asked the president how he feels not just what he thinks or plans to do. That is what caused him to give you a response because you had empathy and could put yourself in his shoes. I’m happy and sad at the same time because of the way I got this job from a very young age. It’s quite insightful. Let’s double-click on the story you have of interviewing Gorbachev, which got cut down from what you originally thought it was going to be in terms of the amount of time you’d have of somebody. Can you paint that picture for us?

Let me take you back to February 2008. Mikhail Gorbachev is coming into town to give a speech about abolishing nuclear weapons. This is years after he was the leader of the Soviet Union. I’m sitting in a hotel lobby waiting to meet him. I’ve got an hour and a half to ask him any questions I want in order to fill up Esquire’s What I’ve Learned column. I’ve done all the research well-prepared and ready to go. The phone rings and it’s a publicist. She says, “Sorry to tell you this but your interview with Mikhail Gorbachev is going to be cut short.” I’m nervous and I have good reason to be nervous because this column that I write is not written in my own words. It’s written in the subject words and those words just can’t be any words. They’ve got to be wise words.

Aim your first question for the heart. Click To Tweet

This situation happens time and time again to people in the business. You’re told you have an hour to present and it comes down to 30 minutes. You’re told you have 30 minutes and I only have ten minutes so tell me what you’ve got or you’re meeting somebody in the elevator and literally have an elevator ride. What you’re about to share of what you do in a situation should have everyone on the edge of their seats because it applies to business.

When I talk to salespeople I could see on their faces when they hear this how attached they are to that situation because it must be happening to them every day. Here I am, I got the phone in my hand and I know that there’s no way for me to fluff this column up or fill it out. I need Gorbachev’s words and I need at least an hour in order to reach into his soul and extract the wisdom to fill up that column. I leaned into the telephone and I asked the publicist’s, “How much time have I got?” She says, “Ten minutes.” I go crazy, “This is impossible. I can’t do this in ten minutes.” She was like, “Cal, a lot of very important people have been added to the list to see Mr. Gorbachev. There’s nothing I can do about it. Do you want that time or not?” Of course, I take the time but as I hang up the phone, I’m feeling worse about this. I know I’m going to walk in that room and we’re going to shake hands. We’re going to exchange pleasantries, we’re going to be seated and there are two minutes right there. Plus, my questions are going to have to be translated into Russian and his answers back into English. It’s another two minutes right there. This interview is down to six minutes before it even starts but you can only do your best.

The point of time arrives. The publicist escorts me into the conference room and I look in there and a smile comes over my face because there he is. I walk up to him and I know I’ve got to do something to get the time back. I know that doing things in a normal conventional way is not going to work. I’m looking at him and I get this feeling that he’s expecting my first question to be about nuclear arms or Ronald Reagan or world events. I quickly jump in and say, “What’s the best lesson your father ever taught you?” He was surprised in a pleasant way. He looks up and doesn’t say anything. He’s looking at the ceiling as if he’s seeing a movie of his childhood on it then he starts to tell me a story. It’s a story that goes back to when he was a boy and his dad got called up to fight in World War II. The Gorbachev’s lived on a farm. He was describing the trip that the family took from the farm to the town in order to see the dad off. He was doing it in nice details and I’m sitting there wondering, “This is amazing. I didn’t see this in research.” Another part of my brain is screaming, “Wrong question. This interview is going to be over before Gorbachev’s even get to town.” They don’t get to town. When they get to town, Mr. Gorbachev takes everybody in the family into a little shop and he buys them all ice cream.

TSP 194 | Big Questions

Big Questions: It’s not going to help you even if you have the best question if you’re not listening to an answer.


Gorbachev is remembering this ice cream. He’s remembering the aluminum cup that it was served in. He’s talking about this aluminum cup of ice cream as if it’s sitting in the palm of its hands. The more he talks about this ice cream, the more we both have this realization. This cup of ice cream is the reason he was able to make peace with Ronald Reagan and end the Cold War. This cup of ice cream contains the moment that he could just imagine might be the last moment that he’d ever see his dad. It was a dread of not knowing what was going to happen from this point on. He’s looking at the ice cream, I’m looking at the ice cream, we both look up at each other and we’re thinking, “This is deep.” Just then there’s a knock on the door and it’s the publicist, “Mr. Gorbachev time for the interview to conclude.” Gorbachev looks, the publicist looks at the translator, looks over at me and he says, “No. I want to talk to this guy.” The publicist is surprised but she backs out the room. The conversation continues and goes deeper. About ten minutes later another knock on the door. This time the publicist comes in a little more sheepishly, “Mr. Gorbachev, Cal.” Mr. Gorbachev’s says, “No. I want to talk to him.” The publicist backs out the room.

Ten minutes later, the conversations got deeper and deeper and another knock on the door. This time the publicist is in an all-out panic, “Mr. Gorbachev, Cal, please. I get a long line of people outside the door to see Mr. Gorbachev. I don’t know what we’re going to do. The day is way off balance already. We’re never going to have time to do everything that we’ve set out to do. Please.” Gorbachev looks at her translator and looks back at me and then he gives me this shrug that says, “What can I do?” The interview ends but at that point, I had enough to write the What I’ve Learned column and it turned into a huge success. When I thought back on why, I realized that if I hadn’t aimed my first question for his heart, never would I have gotten that insight. If I got him with a canned question, I would have got a canned answer. The interview would have been over in six minutes and I’ll never know what was possible. That’s what I always recommend to people that when they’re in that situation, they always aim their first question at the heart.

The reason I love that is it automatically paints a picture again of drawing an arrow and aiming it. It’s vivid. Before the show started, we were talking about you have three things that a question is part of that allows for a successful pitch to happen. Would you take us on that journey and describe a little bit? If you’ve got a good question then what comes after that and then what does that lead to?

I never learned anything while I was talking. Click To Tweet

You start with the question but it’s not going to help you even if you have the best question if you’re not listening to an answer. Here’s your next tweet, John. It comes straight from Larry King the broadcaster and a legend. Larry likes to say, “I never learned anything while I was talking.” It’s so crucial to be an active listener. Once your sincere question is out there to be taking in the information because people will know how much you care by the way you’re listening. They can often look at your face and understand whether you’re standing there thinking of what you’re going to say next or listening to them. That leads to the story because now you’ve asked the question and you’ve got some information. Once you can frame that information in terms of a story, you can then make a pitch or try to compel somebody with something that may have happened in your past or that you know about. It is within you at the start but you need the question and you need the listening in order to know exactly the story to put forth in order to craft it in the right way and with the right timing.

I would be remiss as a host if I didn’t ask you to tell us a little bit about the story you wrote when you won the James Beard medal for your experience of being the sommelier at Windows on the World at the top of the World Trade Center.

That goes back to a moment where a new editor was taking control of Esquire magazine. This went back to late 1997. David Granger came in one day with a group of his writers passed magazine experience and he needed stories. You just suddenly have to fill magazines for a few months all of a sudden. I came up with this idea called The Perfect Man. The only reason I could have that idea was that I had so many flaws to correct. The idea was to look at my flaws and then go to experts to find out how to correct them and to be better than I was before. I did this across a variety of subjects. I learned to eat with etiquette and to manage my time. I learned to do things as simple as walking with the right posture, even how to shave in the best way. I was following all of these areas of my life that I wanted to be better at. One of the things about wine is if you don’t know anything about it, you can be humbled. When you are the host at a dinner table and the wine list comes around people will look at you to select the wine and you don’t know how to match it with people’s foods. You don’t know what’s good and you don’t know whether wines are worth the money. You never know if the waiter or the sommelier is trying to jump you.

TSP 194 | Big Questions

Big Questions: The best questions are questions that make the person just as curious about the answer as you are.


What happened is we arranged for the folks at Windows on the World at the top of the World Trade Center to take me in. At one point, Windows sold more wine than any other restaurant on the planet. It was a huge restaurant. It was so beautiful because you’d have the windows that allow you to see the panorama of New York. It became the ideal spot for a man to take the woman of his dreams to dinner and then get down on a knee and propose and everyone in the dining room would start applauding. It gets more romantic than that in a lot of eyes.

Something you just said that I hadn’t thought about before was clearly that restaurant was all windows from floor to ceiling. When you’re sampling wine, you’re looking at the windows that the wine creates in the wine glass. I love that double meaning there.

I don’t know anything, John. They took me in on a two to three-year adventure. I wasn’t working at the restaurant every day but when I could, I would stop in and they taught me all about wine service. I had to go out and learn all about wines and the differences between all of the different types of grapes and where they came from. You had to be able to describe the sense and the taste. It is a long process. I don’t know if you’ve ever seen the documentary, SOMM. I recommend this to everybody. It doesn’t matter if you like wine or not. It’s a documentary about excellence and it shows a few guys going through a test to be a master sommelier and what they have to do in order to achieve that grand status. Hardly anybody passes this test because you have to be able to pick up a glass without knowing anything but what you’ve just tasted you’ll say, “This is the country that is from. This is the region in the country where it’s from. These are the grapes that were used and this is the year that the wine was made.”

If you give people a canned question, then you would have a canned answer. Click To Tweet

The amount of information that you have to accumulate is stunning. I didn’t do anything near that but for me to understand where all the wines on the Windows wine list came from and what they tasted like and to know enough about the grapes to talk about them. It took more than two years. Whenever I was traveling around the world, I would stop in the wine regions. It was beautiful the way the wine world opened up to me. Everybody embraced me and poured their wines for me and allowed me to taste. One night in 2001 shortly before the planes came in and took the World Trade Center down, I was the sommelier there. It was a glorious night. The beauty of it was there were many people who had no idea I was just doing this to write an Esquire magazine story. They thought I was the sommelier.

Very few people have the time and the luxury of being funded for two years to learn the job so well that you can write a story about it.

That was the great thing about my experience with David Granger and Esquire. If you had a great idea, he’ll go with it.

It’s almost like being undercover for the police and your identity starts to blur a little bit because you’ve become such an expert in that that you think, “This is my new career. Who needs journalism?” When the planes crashed into the towers and Windows on the World no longer existed, did you feel as if you lost part of your identity?

I had many feelings going through me. I felt odd because I didn’t know any of the people who were on those floors at the top of the World Trade Center because I was working at night. There was a whole different group of people working in the morning but there were certain people like General Manager Glen Vogt and the Head Chef Michael Lomonaco that I knew they were there all the time. Miraculously, Michael was coming into work at that time and he stopped to pick up a pair of glasses. Because he did, he was not at the top of the World Trade Center when the plane hit and is alive and Glen survived as well. I felt so close to this place. I remember having dreams of all the bottles and the wine cellar just tumbling into the abyss. You feel so connected to all the beautiful moments that that place had provided and all the beautiful moments that it had given me. The reaction I had was it was hard for me to drink wine for a while after that. I don’t think I’ve ever returned to the place I was at when I was a sommelier and the wine was that integral in my life. It was something that I was thinking about for hours in a day. It’s hard to answer the question because so many emotions ran through me.

They had a fundraiser to help out all of the wait staff and restaurant folks who lost their jobs. It was a beautiful dinner. Wines from around the world donated some of their best wines to be auctioned off so that the money could go to help support the restaurant staff and waiters. We’re in the middle of this beautiful evening and they start announcing the different people who would help put this fundraiser together and they were announcing the sommeliers of various restaurants. They announced like, “Sommelier from Windows on the World.” They mentioned my name and the place wraps with a roar and applause. I felt odd like, “I’m not the sommelier. I’m an impostor. I’m a writer who’s just doing a story and here is everybody jumping to their feet in support.” There were so many feelings that came out of this that moved me and almost crippled me because it was my job at that point to write a story about the experience and I couldn’t write it. I’ve heard of people having writer’s block. I never had that experience but it was too close. It took me ten years to get the distance to be able to look back and understand what I’ve been through. I did write the story at that time and it won a James Beard Award. That’s the best thing I’ve ever written.

People will know how much you care by the way you're listening. Click To Tweet

You’re not only a great writer and interviewer but you’re also a great keynote speaker. I want to touch on some of the places you’ve spoken up and your fundamental idea that changing your questions can change your life. That allowed you to speak to Facebook, Twitter, Apple Music and UCLA. In fact, Facebook Marketing said that your technique has become a staple in the department. They have people using the term Cal question, “What Cal question are we going to use to get the understanding we need?” You changed their culture. Cal, can you leave us with what is a Cal question?

On my podcast, I ran a contest with a Cal question. The question is, “Why is your best friend your best friend?” The reason that I like that question is it does many things. One, it’s not threatening at all. It allows somebody to speak intimately about themselves without feeling that you’re prying into a dangerous place. Two, it brings the person who has the question coming at them their best friend. It makes them warm and it makes them happy to think about their best friend. Three, it’s not a typical question. It forces them to think about something that they know in a deeper way. The best questions are questions that make the person asked just as curious about the answer as you are or maybe they’re even more curious than you are to get to an answer. Here they are with their friend in mind and now they want to look into themselves in a deeper way to find out, “Why is my best friend my best friend?” When they do come to that answer, they’re going to be happy that they’ve got that question and they’re going to look forward to the next question.

Cal, I can’t thank you enough for sharing with us your journey and your insights about what it takes to get a good question that strikes at the heart and how we can learn to listen better and become storytellers so that every pitch we are on is framed in a whole new way. If people want to find you, they can go to your website, They can listen to your podcast, Big Questions. Do you have any last thoughts you want to leave us with?

I must say I’ve known you for a very short time, John, but I feel very close to you. We are almost mirror images of each other in terms of where our careers were. You were on the advertising side and I was on the editorial side but we’re seeing that it’s all much bigger than this fragmented way of looking at things. What I’m discovering through the time I’m spending with you is that it’s the questions, the listening and the storytelling that work across the board.

Thanks. It’s been a pleasure having you on. There are so many more things people could ask you. I just added my own questions because I feel you on the other side of the things. I could talk to you for hours. I appreciate you sharing your wisdom with us and I’m looking forward to watching what your next question is going to be.

The best is yet to come, John. I look forward to seeing you down the tracks.


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