Podcast Episode

Ask Better Questions, Get Better Answers

with Cal Fussman

Episode Notes

Cal Fussman, a renowned journalist and raconteur, is a New York Times bestselling author, masterful storytelling coach, and world-renowned interviewer who has sat down with icons like Jimmy Carter, Muhammad Ali, and Richard Branson. Cal has an extraordinary ability to foster authentic connections and ask powerful questions that reveal profound insights.

In this episode, Cal shares his journey from writing letters as a curious child to interviewing some of the world’s most influential figures. They explore the power of storytelling, the importance of vulnerability, and how listening intently can transform your business interactions, particularly in sales. Cal’s unique experiences, including traveling the world on a limited budget while relying on the kindness of strangers, have enriched his approach to interviewing and storytelling. 



  1. Ask thought-provoking questions.
  2. Become an active listener. 
  3. Emphasize personal stories.


Connect with Cal Fussman

Website: www.calfusman.com 

LinkedIn: https://www.linkedin.com/in/calfussman/

Connect with Jeffro

Website: https://www.frobro.com

Social Links: https://www.tiktok.com/@frobroweb


00:00 Became close friends, cared for him deeply.

05:52 Overcoming setbacks in work and education.

08:33 Curiosity about vice president, letter from president.

13:53 Active listening matters for building trust; Larry King.

16:10 “Listening is crucial in sales, not interrupting.”

19:40 Ask meaningful questions to engage and win.

24:17 Success lies in mastering the basics consistently.

25:57 Tim Ferris podcast guest shares insightful discussion.


Cal Fussman [00:00:00]:
I actually encourage people to think about their stories because quite often, they could be more powerful than the numbers that represent them. 

Jeffro [00:00:18]:
Welcome back to Digital dominance. This show has always been centered around digital marketing because this is an area of growing importance as our society becomes more and more online oriented. Now a lot of people think that if you figure out the magic combination of software and automation, then that’s all you need to be successful. Tools are, of course, important, but we’ve also spent multiple episodes talking about knowing your target customer. Because once you know them, you can communicate with them and create a connection. A well researched and well written sales page that is ugly will drastically outperform a flashy sales page that was thrown together at the last Digital. And that’s because there are people on the other side of that page, and it’s the people that matter. So to continue this human centric marketing focus, I’ve invited Cal Fussman on to the show.

Jeffro [00:01:01]:
Cal seems to have the Midas touch when it comes to asking great questions and fostering authentic connections. He’s a New York Times bestselling author. He’s a masterful storytelling coach, and he’s been captivating audiences for decades. When you hear Cal speak, he’s pulling from an extensive history of conversations and interviews with household names. He sat down with world leaders like Jimmy Carter, Nelson Mandela, sports figures from Muhammad Ali to Kobe Bryant, and many entrepreneurs and celebrities from Robert De Niro to Richard Branson. So I’m super excited for our conversation today. Welcome to Digital dominance, Cal.

Cal Fussman [00:01:33]:
It is an exciting day for Cal Fussman to be on a podcast called Digital Dominance. So I’m really happy to meet you, Jeffro Roe, and looking forward to seeing where this is all going.

Jeffro [00:01:46]:
Yeah. Yeah. Well, I’m really happy to have you here. You know, earlier this week, I was going through your LinkedIn profile, and I love that you included the role of caretaker for your dad just as if it was like any other job. Right? You know, I think a lot of people try to paper over gaps in their employment because I don’t know if they’re embarrassed or maybe they put something in there like freelancing consulting work or working on my novel. Yeah. So what prompted you to include that?

Cal Fussman [00:02:09]:
So what happened was I was living in LA between 2,008 and 2,020 and moved out to help Larry King, the CNN broadcaster, write his soup to nuts autobiography.

Jeffro [00:02:24]:

Cal Fussman [00:02:24]:
And I ended up becoming very close friends with him, and we had breakfast almost every day for 12 years whenever we were in town. And when the COVID hit, basically, all the restaurants got closed, and Larry had some health problems. And my dad was turning 90 in North Carolina, and so I just knew I had to go back and just take care of them during this time. So my wife and I moved back to North Carolina, and we took that year, a little more than a year, and just were with him every day and had dinner with him every night and watched a movie with him every night, sometimes a double feature. And it’s a decision I will never ever regret. And it wasn’t like one of those movies where there were all kinds of problems and they get resolved at the last second over the bedside. You know, we had basically talked everything out, but it was really being there day after day after day, and he’d, at one point, dropped his iPhone and went to pick it up, and he fell and broke his pelvis and had to go into rehab, and we were just there. And it was it’s a beautiful thing to do.

Cal Fussman [00:04:00]:
Everybody’s got different relationships, but if you can help somebody who has given you their everything free from the time you were born, if you can step in and help them when they need it, it it’s a beautiful feeling.

Jeffro [00:04:18]:
Yeah. Well and I think there’s other people that might choose to do that and take care of a family member, but they wouldn’t put it on their resume or LinkedIn profile. Right? And that I think really reflects on you as the kind of person you are who’s transparent and, you know, it humanizes you and allows people to relate to you. But, yeah, do you have any other comment on that?

Cal Fussman [00:04:36]:
Well, I the only thing I can tell you is people have actually written or emailed me to or written on LinkedIn. Wow. Like, you never or very rarely see experience listed that way. And in fact, the bulk of what people know me about was work that I did for Esquire Magazine where I interviewed the icons of the last 75 years. And because of some of the experiences I had that I put up at top, you you actually have to click to go down and see what I’m kinda famous for. And it it was actually been pointed out to me, you know, Cal, you really should bring that up because a lot of people wanna see that first. So I may it made me think, but I decided to keep it up there because it’s like you’re saying, it’s authentically me. And if they’re really interested, they’ll keep they’ll keep clicking.

Jeffro [00:05:42]:
Yeah. Well and I think you’re setting a good example for others to show, you know, you can let people know that you have a personal side. We all do, obviously. So sometimes it’s kinda silly to try and hide that.

Cal Fussman [00:05:52]:
You know, some there’s another point, Jeffro, here that a lot of people are either they don’t understand or they may be too scared to take the risk. I can produce a metaphor that anybody in the working world could understand. If you if you have a bad experience in the working world, obviously, you you don’t want it in front of everybody. You just wanna move on and and prosper in the next step. But I I heard a story of a young man who when COVID hit, he was in high school, and he it just knocked knocked him for a loop. And in I think it was his sophomore year, his grade point was 0.00. And so what but he recovered, it might have been his freshman year, but but you’re starting you’re starting with a year of 0.00, and he got it up to, like, a a 33 or 34 by being almost perfect. And yet, if you just look at the final result, like, the top institutions would just say no.

Cal Fussman [00:07:05]:
No. Like, the the computer is just gonna throw them off to the side. And my point is that the story of what he went through to get that 0.00 and then come back and and be nearly perfect to lift himself up to a pretty high level, but not to the level where you can get into a Ivy League school. The story is more important than the numbers. And a lot of people don’t realize that, and and that’s 1. Number 2, in every story is vulnerability. There is just no good story without essential vulnerable character. It just doesn’t exist.

Cal Fussman [00:07:53]:
If the if the sense of character is not vulnerable, nobody’s going to lean forward to see what happens. And and so I actually encourage people to think about their stories because quite often, they could be more powerful than the numbers that represent them.

Jeffro [00:08:11]:
Right. Well and I love how you’re able to focus on that and draw it out because, like like you said, everybody skips over that. You know, when we look at the Olympics, we remember the people who got first place, not necessarily the ones that overcame impossible odds and only got second place. Right? You know? So I I love that you focus on that. And do you think that is one of the things that makes you special as an interviewer?

Cal Fussman [00:08:33]:
What makes me special as an interviewer goes back to a time where I was about 23 or 24 years old. To to backtrack, if I was telling this story over 2 hours, I would start with the fact that or the story of how when I was just turned 7, I was in 2nd grade, and president John f Kennedy was was shot. And the teacher came, left the room, came back in. A different person told the class we were all sent home. And I, having just turned 7, I I couldn’t figure out what it’d be like for the vice president to step up and take that oath of office. Like, how did he feel? Was he happy to be the president? Was he sad because it was only because of the assassination? Or was he scared because maybe he thought they would try and kill him too? And so I sat down and I wrote the new president a letter. And 6 months later, I’d I’d forgotten all about it that I put it in the mailbox. I got a letter back from Lyndon p Johnson, And it was a letter that kinda changed my life because I knew that if you understand the power of a question, you get to the most powerful person on earth.

Cal Fussman [00:10:02]:
And so I knew I would be asking questions. Many people don’t know what they’re gonna be when they’re 7. I understood it. And my dream as a kid back in the days where newspapers were the biggest way of communicating, like, in a city, I expected to be that person who wrote a column and you could see their face, and every day, you picked up the paper to see what they had to say. And I went to school. After that, I graduated and basically got to a big newspaper and saw my face in that paper writing a column. And a lot of things happened, but the the bottom line is I had to make a choice. Am I going to now do this for the rest of my life, or is there something bigger out there? And I took time off to travel just to see different things, and this is where the answer to your question really zones in.

Cal Fussman [00:11:03]:
Like, what made you interview the way you do? Mhmm. I didn’t have much money and very little. What I would do is I would go to a train station or a bus station, and I would buy a ticket to a destination. It didn’t matter where it was going. What mattered to me was the empty seat on the train or the bus and the person that it was next to. So I was gonna sit in that seat, and I knew when that train started rolling, a conversation was gonna get started. And by the end of that trip, by the end of that conversation, I basically needed them to, like, invite me home and ask if I I’d like to stay or if I’d like to have dinner because I had no money not enough money to spend on hotels. And so what happened is when I started to sit in that seat and people started to invite me home, they then created parties because it was like something exotic was happening.

Cal Fussman [00:12:07]:
This this is a day before the Berlin Wall came down. So now I’m, like, the centerpiece of a party meeting all these people who are then inviting me to their homes, and then telling me about their relatives and sending me their relatives. And I traveled this way for roughly 10 years without a home, going around the world to where people pointed me to or I may have just bought a ticket and got on the train and looked for that empty seat. And it was in that empty seat that I learned trust because I literally was asking people to trust me enough to take me home and offer me a bed to sleep that night. And that trust is what went into all of the interviews when I came back, and I’m interviewing Mikhail Gorbachev who became the last leader of the Soviet Union or Muhammad Ali. They they felt that, and so the interviews often were different from anything that they encountered, and that’s where it came from.

Jeffro [00:13:18]:
Right. Well, I mean, that’s amazing because a lot of people who are journalists or any viewers, asking questions a certain way is a skill they learn in journalism school. But for you, it this was a way of life. This was a matter of survival, literally. And so it just comes out of you naturally. You have to be authentically interested in the person and caring about the answers to their questions and listening to what they’re saying. And that’s just that’s that’s you. Right? There’s you’re

Cal Fussman [00:13:53]:
that’s a great point, and I’m happy you brought up the listening because that is what makes all the difference. And, you know, Larry King once told me he was interviewed all the time, and it would drive him crazy when interviewers showed up with notebooks with their questions, like, written out 1:1 to 20 or whatever and just following what they wrote down instead of listening to what he was saying and responding it to it or amplifying it. And so one time, a woman was going through those questions, and she actually after she would ask the question, she was, like, looking down at her nails or and she wouldn’t even caring about what he said and then moving on to the next question. And so he just started inventing answers that had nothing to do with the questions, and she just kept rolling right on. And I I don’t I don’t know only Larry King would do that because he was a comedian at heart. If he hadn’t been the guy on suspenders asking questions, to world leaders, he would have wanted to be a stand up comic. So but it brings back to your point. If you’re not listening, nobody’s gonna trust you.

Jeffro [00:15:16]:
Right. And you’re never gonna get past those surface level answers. Right? There there’s no reason to open that door.

Cal Fussman [00:15:21]:
And will wouldn’t the same apply for sales?

Jeffro [00:15:24]:
Exactly. Yeah. And, I mean, that’s the natural segue into this. Right? We have business owners listening. And, you know, if you wanna understand how does asking good questions apply to a business, this is how. Right? Sales is really about connecting and trust. You know? Because customers have so many options, they can Google find dozens of options in their area for who to hire and work with. But when they’re on the phone with you, you know, your job isn’t to say, okay.

Jeffro [00:15:48]:
Here’s our packages. Which one do you want? You gotta find out, okay, what’s the actual problem here? Because sometimes you gotta dig a little bit. Maybe they’ve tried something before, the thing that you offered, and it failed. But you won’t know that until you’ve uncovered and talked to them and kind of listened and drawn that out because then you can actually address the issue that they have, not the one you assume they have.

Cal Fussman [00:16:10]:
You know, I went into a company to monitor a sales team because they wanted to see, like, how the sales team was asking questions, listening, and telling the story about the product. And we went through this a few times, and the leader of the sales team was talking to the group about it. And he said, you know what the difference is between Cal and us? He’s actually listening to the answers. You’re already thinking about what you wanna say next to make the sale. But the reality is if you’re listening and people can see when you’re listening, they can sense it, and they can sense when you’re just allowing the words to come out and waiting for the pause so that they can jump in with the pitch. And listening is so important, and I I get it in sales, there’s you got a quota. The time is really important. You gotta get your information out.

Cal Fussman [00:17:23]:
You gotta move things forward. But you know what? Maybe just taking a little more time to actively listen would pay off big time as the process keeps rolling. Right.

Jeffro [00:17:39]:
You gotta slow down to speed up, because otherwise, you’re gonna have a lot more sales calls before you get one closed. Whereas if you spend a little time in each one, alright, you’re more likely to get more closes because the people feel like you’ve heard them, you understand their problem, and you are able to fix it. You’re not just forcing something on them because that’s your job.

Cal Fussman [00:17:57]:
There you go.

Jeffro [00:17:58]:
So that’s, you know, an interesting dynamic when you’re 1 on 1 back and forth in business owner wants to run a survey to their clients? You know, there’s no back and forth, but they wanna know what their clients think. You know, they can be intentional, you know, really wanting to understand this. But how should they approach writing those questions in order to get the most helpful and meaningful answers, you know, and feel like they’ve been heard and understood?

Cal Fussman [00:18:25]:
You know, that’s so interesting because I came upon a company that actually pays people to, like, play video games for for money. Like, if you reach a certain level, you get a certain amount of money in a certain amount of time because the company wants to understand how the players are thinking. And companies have surveys that they want filled out just like and they’re willing to pay, to have those surveys pulled out because it a lot of it is the the timing that we have. I mean, think about it. If somebody wants to ask you 20 or 30 questions, and you’re in the middle of a packed day. Are are you gonna even give it a look? Nope. No. So it really does seem to me that if it’s at all applicable to incentivize with something maybe from the product so that people will say that this is a good deal to take this survey.

Cal Fussman [00:19:40]:
And and then making the questions coming up with questions that make people do do this. They’re they have to think for a second. It it it’s not just yes, no, yes, no. And then when somebody is forced to think that way, they’re appreciative of the question because when you’re looking up like that, you’re reaching deep into yourself. And when you’re reaching deep into yourself, it’s important to you. Something deep down, there’s some kind of memory there, And when you pull it up, it has a reaction. And maybe it was a a terrible reaction, and maybe something in the survey is gonna get a really bad mark, but wasn’t that what you were looking for? And so if you can get the customer to just look up and think, which means that they’re really looking down to dredge something up, then you’re gonna win. If if if you’re just asking yes, no, yes, no, yes, no, okay.

Cal Fussman [00:20:47]:
You’re you’re gonna get data, but I wonder how truly authentic it’s gonna be. So And I

Jeffro [00:20:56]:
think the same applies, not just yes and no questions, but also the rate this on a scale of 1 to 10. Because even if they go through that thought process, you now reduce it to an 8, and you have no idea how they got there. So you need the open ended questions.

Cal Fussman [00:21:09]:
Exactly. They you know, there was a a wine critic named Robert Parker, who for years was he literally could determine the prices of the wines that got sent out because before they were sent out, he would taste them, and he would give them grades be generally between, like, 70 a100. And if wine is very competitive, there are so many wines in Bordeaux. If you’re to go into a wine store and you’re gonna look at them, how are you gonna know? Well, it came down to what did Parker say? And what Parker said was a number. And, man, you talk to these people who are making the wine in France. Parker drove them nuts. Like, why is how could they give me an 88? And, like, the difference between an 88 and a 91 was a lot of money, and and it’s completely subjective. And if you have Robert Parker’s taste, great.

Cal Fussman [00:22:21]:
You but what if you don’t and you’re just told, oh, Robert Parker says 94. Great. I’ll get it. So surveys really can probably be rethought to get to what the companies really wanna know.

Jeffro [00:22:40]:
Right. So, I mean, it kinda leads me to my next question, though. You know, as a business owner, they obviously wanna make money. Do you think that the profit motive interferes with someone’s ability to ask these good authentic questions?

Cal Fussman [00:22:52]:
No. I think it overlaps. Man, you talk to the CEOs, they wanna know. They really wanna know, and I can’t imagine that they wanna turn away from the way their customers are thinking about their product. It just doesn’t make sense. Their company depends on it. So putting the time into the questions you’re asking people is a valuable asset. You know? Listen.

Cal Fussman [00:23:27]:
Just look at it this way, Jeffro. And these are the simplest things. This this is talking about childhood curiosity and the ability to ask a transformational question. A question that’s gonna give you information that may not have been expected. And then the power of listening to the answer. And then the power of telling the story of your product based on what you’ve put into it and what your customers have gotten out of it. Those three simple things. You and look, it’s got artificial intelligence and, all the data out there, which I’m all for.

Cal Fussman [00:24:17]:
But if you just went back to the basics, you’re going to get the answers you’re looking for, and I’ll back this up with one story that I just heard, about a coach who he’s coaching middle school and high school players, and then Nike hired him. And he went to a 3 AM workout of Kobe Bryant. And he’s watching Kobe workout, and Kobe is doing these basic drills that he was giving his 7th graders to do. And at the end of the workout, Kobe goes over to him and he says, you know, what do you think? And he said, I don’t understand Kobe. Like, this same drills that I that I’m teaching 7th graders you’re doing, and you’re, like, the best player in the world. And Kobe said, that’s exactly why I’m the best player in the world because I never got bored or tired with the basics. There you go.

Jeffro [00:25:19]:
The fundamentals. So any any good CEO is gonna understand that and want to, you know, get to the root of what drives a customer, what makes them tick in order to move that business forward. So I I I like that that they do overlap in that sense. We are at the end of our time, though, Cal. I love, hearing all your stories. Thank you for spending time with us today. I sincerely hope that businesses continue to become more personal and authentic, and I think your insights can help us move in that direction. So for those of you guys listening, go connect with Cal on LinkedIn.

Jeffro [00:25:51]:
Hire him as your next keynote speaker. Go read one of his books. Cal, would you like to leave our audience with a question to ponder?

Cal Fussman [00:25:57]:
With a question to ponder? What? That should be for a philosopher. But you know what? Tim Tim Ferris had me on his podcast a few years ago, and the question he asked me was, what would you put up on billboards? If you could put up any message to people who are driving by, what message would you put on the billboards? And I I didn’t need to even take a second or 2. I just said, listen. And so I everybody’s gonna have a different answer, but I think that’s a great question. What message would you have for anybody who could put up a message on a billboard? And I think you’ll get to the essence of the person answering that question. And it’s it’s gonna be very different. Most people wouldn’t say, listen. Only I’ll say, listen, and you just found out why.

Cal Fussman [00:27:04]:
But they’ll find out something very I found out something about myself when I answered that question. So I’m happy, to pass it on and very grateful that Tim Ferris passed it on to me.

Jeffro [00:27:17]:
I appreciate that. Well, thanks again for being here, Cal. Thanks to all of you for listening. Let’s all try to ask better questions, be better listeners, and I’ll see you back here for the next episode of Digital Dominance. Take care.

Cal Fussman [00:27:28]:
Thank you, Jeffro.

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