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The "Icebreaker" Gone Horribly Wrong that Turned Into a Gift

Posted on September 6, 2017 at 1:10 AM

The year was 2002. When the new Vice President (VP) arrived at my Fortune 500 company, we had an “off-site” meeting to introduce him to his new team. He was a big shot partner from a high-powered consulting firm who was going to ‘take us to the next level,’ according to corporate communications. As a mid-level manager, I was one of the 15 or 20 people who made up his ‘skip level reports’ – or fancy corporate language for “my boss’s boss.” We each introduced ourself, described our role, and then answered a few innocuous icebreaker questions to include a personal touch. I forgot what the other questions were, but one got burned in my mind.


“What was the last music album you bought?”


In a moment of immature bravado, I decided to be funny with my answer. “I know the last album I acquired was Yankee Hotel Foxtrot by Wilco, but I don’t remember the last time I’ve been to a music store since Napster came out.” Even though I wasn’t a Napster user, I guess I wanted to impress him with how internet-savvy and musically hip I was for a mid-level manager. I also was trying to look cool and funny to my peers.


“My brother helped make that album. He was in Wilco.”


I am not sure what reply I was hoping for, but that definitely was not it. At first, I thought he was joking right back at me. But he wasn’t smiling. I later found out he was serious. And unauthorized, free downloading of songs via Napster was not a funny joke to musicians in those days.


Wilco was famous by 2002, so the odds that Wilco’s Yankee Hotel Foxtrot was the newest CD in my collection were not that long. But what were the odds that our new VP was the brother of Wilco guitarist Jay Bennett? If I could remember the exact date and time of that meeting, I would play that number combination in the Mega Lotto every time.


I don’t remember what happened in that meeting after that. I was in shock after making a self-inflicted, career wound. If there were a contest for “worst first impression with the new VP ever,” I would have won.


After the meeting, the new VP pulled me aside to smile and let me know he was not offended. He was as surprised as I was by the coincidence. From that conversation, we figured out we had similar tastes in music. We later found out we both had a passion for bicycling too.


Fast-forward 15 years later, and the VP and I had dinner this week. Our initial awkward connection had blossomed into an enduring friendship, powered by social media and a surprise meeting or two at airports. We reminisced about our time working together. We also talked about the documentary film project about his brother that we were both following on Facebook. (Jay Bennett tragically passed away in 2009.) When he told me his story about being at a Billy Bragg concert and hearing Billy dedicate “California Stars” to his brother Jay, we both got teary-eyed.


I learned a lesson from this experience. Whenever I have a conflict with someone at work, the good news is it means we share some common passion. We may not agree on how to address the issue, but we can agree that we both care about the issue. We can go back to that common ground to get the relationship back on track. In this story, our common interest in a music group caused an awkward moment at first, but we ended up building on that shared interest to form a lasting friendship. Looking back, I’m glad I fumbled that icebreaker.

Categories: Communication Skills, Meeting Effectiveness, Coaching