New York Times Bestselling Author

Advice from a New York Times Bestselling Author: Ask Questions

This past weekend, I made the trip from Boston to New York City to work an event for Puma. The sportswear company hosted the Kansas City Chiefs’ All-Pro running back Jamaal Charles, and his trainer, Alphonso ‘Zo’ Hodge, on-site to recognize Puma’s New York City trainers. The event was produced by Boston-based startup Exquisite Design Concepts and held at Glasshouse 21, a venue surrounded by breath-taking views of Manhattan. After some issues with travel arrangements, from Kansas City to New York City, Charles was picked up by helicopter at the airport and flown directly to the venue to ensure that the event would still be carried out (just one of the perks of being a star athlete).

At the event, Charles and Zo discussed Charles’ in-season and off-season training routine, his relationship with God, and his inspiring journey overcoming a learning disability to become one of the top running backs in the NFL. The Puma trainers were given free gear, the opportunity to ask questions, and were run through a fitness workout directly from Charles’ routine.

Participants from all parties involved enjoyed themselves, the puma trainers left with new training tips, and the event went smoothly. Overall, it was a success.

Puma trainers look on as Jamaal Charles and  Alphonso ‘Zo’ Hodge talk about the All-Pro Running Back's training routine.

Puma trainers look on as Jamaal Charles and Alphonso ‘Zo’ Hodge talk about the All-Pro Running Back's training routine.

What does this have to do with a New York Times Best-Selling Author?


Well, during my time in The Big Apple, I set up a few business meetings to catch up with some colleagues and make new acquaintances. One such meeting was with New York Times bestselling author, and one of the greatest writers in magazine history, Cal Fussman.

On a beautiful, sunny Friday morning, while the streets were booming with activity—from tourists hustling around to visit famous sites to locals carrying out their daily activities (which mostly entails trying to sell you their mixtape)–Cal and I linked up in a much more calm environment, the café of his Times Square hotel.

The opportunity to sit down with Cal was one that I was going to be sure to take advantage of. We chopped it up about a variety of things—his recent foray into public speaking and the expectation he places on himself of bringing the crowd to their feet in applause, cultural differences of the east and west coasts, the NBA Finals, our sports affiliations, and breakfast with Larry King—which he so graciously invited me to whenever I visit Los Angeles.

I enjoyed my time speaking with such a brilliant person who has transformed oral history into an art form through the art of the interview. As we were about to part ways to go about our day, I had to stop him for one more question. My commitment to personal growth and lifelong learning would not allow me to leave without asking—“Do you have any advice for me?”

His response was brief:

“Ask questions”

Ask questions? This advice only prompted me to have more questions.

That’s it? What do you mean, “ask questions?" What else?

This is a man who is known for a column called ‘What I’ve Learned’ where he shares lessons from interviewing some of the greatest people of the past century—Pele, Richard Branson, Dr. Dre, Al Pacino, Jeff Bezos, John Wooden, Serena Williams, the late, great Muhammad Ali, and countless others—and the best advice he could give me was, “ask questions”? This response was puzzling.

Photo of Manhattan taken from the hotel posted to my Snapchat My Story (@glove13)    

Photo of Manhattan taken from the hotel posted to my Snapchat My Story (@glove13)


New York is known as the city that never sleeps and, later on that night, I found that to be the case for me.

At night I couldn’t sleep, I tossed and turned from the advice that I couldn’t immediately wrap my head around.

I couldn’t help but wonder if I had really taken advantage of the opportunity. I looked back on it. Cal had been asking most of the questions, and I was doing most of the talking.

I felt that I had squandered the opportunity to gain insight to wisdom accumulated over decades of interviews with the greatest icons over several generations, across all fields and crafts.

While I laid in my NYC hotel bed, I thought of his advice over and over. Our interaction replayed again and again in my head.

It finally clicked.

Within our interaction was the answer to the enigmatic mystery that his advice gave way to.

Although the sun had gone down, and it was then a dark night in Gotham City, Cal’s advice would eventually shine through like the bat signal and illuminate my outlook. I finally got it.

There is tremendous power in asking questions.

Whether it was the Puma trainers at the event asking Jamaal Charles questions about his training to learn new tips to implement, or Cal asking me questions that enabled him to learn more about me and who I am, asking questions is vitally important because the answers to those questions have the power to teach you something new and allow you to develop relationships and connect on a deeper level.

Larry King once wisely said:

“Nothing I say to this day will teach me anything. So if I’m going to learn, I must do so by listening.”


To ask questions is to grant yourself with the opportunity to learn. To ask questions is to connect with others, develop relationships, and build your network.

The lesson that I’ve learned is this:

Be curious, listen up, and never forget to ask questions.