Big Question of the Week: How to Get Started

Cal Fussman
3 min readDec 20, 2017

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Of all the questions that people ask me, there’s one that comes up the most.

It’s expressed in different ways because it applies to such diverse areas as job interviewing, sales and dating.

But it always boils down to this:

What do you ask to break the ice and start a good conversation?

Last week, after I mentioned that I wanted this newsletter to be a two-way street, I got a note from a pal with a smart take on this.

His name is Gautam Gulati, and not long ago he had the good fortune of watching a presentation made by one of the world’s great photographers: Platon.

Platon photographed many cover stories for Esquire while I was writing them. You may recognize his style.

I’ve heard Platon speak before, and I’ve found his approach to making subjects comfortable quite similar to mine.

We often find ourselves in the same kind of bind — though his are arguably more difficult. I definitely have more time to warm up a subject during an hour and a half interview. When you have only a few moments to snap a cover photo of Vladimir Putin for Time Magazine, how do you strike up a conversation that, within a few seconds, will make him feel comfortable enough to allow you to peer into his soul?

(Platon engaged Putin by asking him his favorite Beatles song. No, it wasn’t Back in the U.S.S.R.)

I suppose the Beatles question could start an intriguing conversation with many different people. But not everybody. There are young people who may not be that familiar with The Beatles. That’s why I don’t recommend relying on the same question over and over as an icebreaker. I just don’t believe there are special keys that open every lock. Besides, if you think you have that key, you may not be as alert and spontaneous in the moment.

After Platon came off the stage at the annual holiday party thrown by Klick, an awesome health company headquartered in Toronto, Gautam approached the photographer and asked:

“What do you say when you walk into a room to elicit such immediate authentic emotion from your photo subjects?”

Platon responded with a question of his own: “Do you have kids?” he asked.

“Yes,” said Gautam, “a 7 year old and a 5 year old.”

“Do you have to think about what you are going to say when they walk into a room?”

“Of course not,” Gautam said.

“That’s authenticity,” Platon said. “Let the conversation unfold through pure spontaneity and curiosity. Be in the moment.”

Gautam wanted to see what I thought about that.

I am in complete agreement, with maybe one slight alteration. I recommend going into each meeting with the curiosity of a five-year-old.

Cal Fussman has spent the last 20 years interviewing icons who’ve influenced the world. His podcast, Big Questions, can be downloaded on iTunes and Stitcher, or streamed here.

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Cal Fussman

New York Times bestselling author, world-renowned interviewer, keynote speaker and host of the podcast Big Questions.