This conversation, just like Cal Fussman, gets better as it goes. I really enjoy the conversations, that at the end, I walk away saying, man, I’d love to spend more time with him/her….This was one of those conversations. 

He’s known for his skill of asking great questions — yet his talent of storytelling is world class. 

Questions are to illicit responses and engagement — and — there is so much more beneath the surface of an answer — body gestures, emotions, hints of motivation, and ultimately, snips of the framework that the person is working to share how they understand the world (and people). It’s all in there — does the responder orientate to protect, to embrace…. to explore, to have fun? And — Cal takes that understanding to the next level by doing it artistically through storytelling. 

We all have a story — thousands of stories. Cal pulls back the curtain to share his — and the challenge is set for us all to become better at asking questions to learn other’s stories — and — to become thoughtful on how we share our own stories with people who are thoughtful — caring — interested — enough to offer their time and attention. 

This is a two-part episode — it’s too good, way too good to cram. When you listen to Cal’s stories, listen for the framework, for the stuff underneath the surface — and — also see if you can listen to how he constructs his stories. 

We also talk about the art of interrupting others — during storytelling — He doesn’t — I do, and we have fun with it (and if you’ve ever wondered why I purposefully  interrupt folks — it’s all by design, and we talk about it just a bit in this conversation).

“Asking ‘why?’ makes a person who knows something about a subject think deeper about it. Just the word why. It makes you stop and look inward.”

In This Episode:

  • Moving to LA to help Larry King write his autobiography
  • The art of speaking less in an interview
  • His thoughts on interruptions during interviews
  • Why you should never ask a two-part question
  • His favorite question to ask… “Why?”
  • Breaking bread with Robert De Niro
  • Learning patience and storytelling from his mom during his adolescence
  • Not having money and wanting to do something different than dad
  • How his internal drive to explore led him to riding trains to new places
  • Why he would never sit next to an empty seat
  • His process for organizing his thoughts and putting them on paper
  • His ability to listen, put himself in someone else’s shoes and feel what they feel
  • Curiosity as a driving force in why he does what he does
  • The lesson he received on not discriminating against those of beauty and fame
  • Being ordinary in front of extraordinary people
  • Why he gives a gift to everyone he interviews



“Some people can listen, but they can’t stop from getting in the conversation. I will let you talk, I’ll give you the chance to tell a story.”

“Very rarely will I ask a question that has a yes or no answer. I always to try to start with ‘why?’”

On asking multi-part questions: “If you ask four questions, you are not going to get the answer.”

“I can be on the phone and somebody’s talking and I can get their feelings through their words.”

“If someone’s disrespectful to me I’m curious what’s in their mind that’s making them disrespect me. Why are they that way? What happened to them that’s making them act this way?”

“People will think about a gift in a different way once a story is attached.”


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Writer at Large at |

Cal Fussman is a New York Times bestselling author, writer-at-large for Esquire Magazine, keynote speaker and corporate culture consultant.