A Wine Time to Dine – Director’s Cut
This is a leadership self-awareness story I’ll never forget.
I was about 27 when I got invited to The Leadership Challenge — a big-deal development conference at our company’s home office. It was where the up-and-comers went to “sharpen their leadership skills.”
To be honest, I didn’t belong there. The room was full of sales managers, store directors, and polished professionals who looked like they’d been born wearing sport coats. They were sharp, confident, and had that corporate swagger. I was just a warehouse guy trying to figure out which fork to use.
Still, I felt proud to be included. The sessions were good, the discussions deep, and for most of it, I managed to look like I knew what I was doing.
Then came the final night — a big dinner in Boston.
We loaded onto a charter bus, and to my delight, the driver had a cooler full of Heinekens. I figured, “Well, this leadership thing’s looking up.” By the time we reached the city, I was three deep, feeling confident, and ready to network with the upper crust of the company.
At dinner, the red wine was flowing, and so was I. The crowd was friendly, and somehow, I’d become the life of my end of the table. For a while, I thought, “Hey, maybe I can do this corporate mingling thing after all.”
Then someone at the front stood to talk about the company’s BHAG — big, hairy, audacious goal — and asked if anyone else wanted to share what their teams were doing. Silence.
I thought, “Here’s my moment.”
I stood up, slurred my name (as I later learned), and shared a few thoughts about something we were doing back in the warehouse — because obviously, that’s what everyone wanted to hear about at a leadership dinner full of store and sales managers.
People clapped politely, which in hindsight was probably mercy applause.
Then, a man across the table stood up. He gave his name and title — a senior European executive. Oh… so that’s who I’d been talking to all night. He thanked everyone for coming to his leadership event and wrapped things up like the host he was.
That’s when I realized: I’d just given an impromptu speech at his dinner.
The bus ride back to the hotel was… reflective. Nobody said much, and honestly, I didn’t blame them.
But here’s the thing — it didn’t wreck my career. I never saw any of those people again. What it did do was give me one of my first true leadership lessons:
Using alcohol to join the conversation is understandable.
Using too much alcohol to become the conversation — that’s a different story.
I learned that night that leadership isn’t about how loud you are in the room; it’s about how you carry yourself when the room goes quiet.
At least I got a round of applause — even if it was just to make sure I sat back down.
