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Breaking Through – The New York Times

In a meeting at work last week, my colleague told the story of how she recently took her son, age 17, to his first concert, Kim Deal at the Brooklyn Paramount. She was so excited to blow his mind, to introduce him to the magic of live music that she’d discovered at 15 when she first went to a rock show herself. How cool, I thought, imagining her son, forevermore when asked “What was the first band you saw live?” getting to answer that he went with his mom to see a rock icon like Deal, bassist and frontwoman of the indisputably hip bands the Pixies and the Breeders. This occasioned everyone at the meeting revealing the first band they saw in concert.

Perhaps more than any other bit of personal trivia, I find this one fascinating. You learn about their teenage tastes in music. If their parents took them, you learn something about their childhoods. (“Oh, he had the kind of parents who took their 6-year-old to see Steely Dan!”) My colleagues’ first concerts were impressive: Duran Duran, R.E.M. on the “Monster” tour. Mine was the English rock band Squeeze, age 15, third row, Madison Square Garden.

And people love to tell you about their first concerts. It’s a jewel box of a question, an invitation to reveal something unique about themselves , to tell a well-practiced personal story. They get to convey as much or as little about your taste as you feel comfortable with — “See, I’ve always been cool” or “God, look what a dork I was.” It’s the perfect specimen of that most reviled form of corporate get-to-know-you activity: the icebreaker.

I have, over the past few days, conducted an unscientific but wholly convincing study of my friends’ feelings about icebreakers. They all, to a person, hate them. I get it. On their face, team-building exercises of any sort should be treated with suspicion. Icebreakers are meant to loosen people up. How loose, one might wonder wisely, is it ever appropriate to get at work? We’re going around the table stating our favorite breakfast cereals, innocuous enough, but I’m not sure I want to reveal anything more intimate than that to the entire marketing department.

But, as cheesy as they can be in a work context (is there anything more humiliating than trying to conjure “a fun fact about yourself”?), I will defend a good icebreaker as a delightful shortcut to a measured intimacy. In a past job where I ran a weekly staff meeting, I began each meeting with an icebreaker. A good portion of my team was remote, before remote work was normal, and it seemed impossible that we were going to get comfortable with one another without some kind of corny intervention. I may be deluding myself, but once the team members got to know one another a little, the icebreakers became a fun parlor game, a way to get closer, to remind ourselves that we were interesting, dynamic human beings even in the matrix of the workplace.

Looking back at my icebreakers from those weekly meetings, I see in my notes questions I have no idea how the people closest to me would answer, and I’m tempted to ask them. Some of these questions I devised myself, some came from the writer Rob Walkers’s newsletter “The Art of Noticing,” some came from the team. “What’s the first thing you bought with your own money?” “What were you doing at 23?” “What’s something you’re great at but hate doing?” “What are the most common things people say when you tell them your hometown?”

It might feel awkward or artificial to pose these questions in the middle of a regular conversation, but it might be fun to deliberately ask an icebreaker of your family at dinner, or a group of friends about whom you think you know everything, or your spouse. For those of us who understand the utility of small talk but deplore the slow, inefficient on-ramp of get-to-know-you questions — where are you from, what do you do, any siblings? — icebreakers do just what they claim to. You can wait for the ice to melt, or you can just smash it with a question that gets at something actually a little interesting, a little revealing. And you don’t have to call them icebreakers. Outside of a corporate framework, icebreakers are just manifestations of curiosity. What do you really want to know about the person you’re talking to? Why not just ask them?

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