The Olympic Leadership Mistake: An Awkward Conversation I Avoided
Imagine not realizing you’re being invited to a fancy party.
Someone picks you up and takes you there. Suddenly you’re surrounded by caviar, champagne, men in tuxedos — and you’re painfully aware you’re wearing a ripped t-shirt and old track pants.
That was me. Only the “party” was the Olympics. Watch the video to learn what happened.
At the time, I was head of content at a national news network. I was asked to come up with a plan for how we could broadcast live during the Winter Olympics in British Columbia. The problem was that if we did anything — and that was a big if — there were only a few thousand dollars available.
Doing anything at the Olympics is expensive. So I built the best plan I could. It was small. Very small. The budget was so tight I literally had thirty dollars for an intern’s lunch in it.
Then I found out our U.S. sister network was going big. They saw the Olympics as an opportunity. We were treating it like an expense.
They were ten times our size and willing to spend about a hundred times the money.
I didn’t understand the size of the gap until my boss invited me to a meeting. The U.S. team wanted to talk about partnering resources.
They were discussing satellite trucks and expanded crews. We were hoping for one camera and maybe a parking pass.
When it came time to show my budget — including the thirty dollars for lunch — my counterpart reviewed it, paused, and called it “an interesting document.”
Yes, I was embarrassed.
But looking back, the real awkward moment should have happened earlier.
I should have asked a simple question: Are we treating this like an opportunity, or an expense? Because right now we’re pretending it’s both.
Leadership Lessons
• Avoiding a strategic question doesn’t eliminate it. It delays it.
• The awkward meeting often reveals the conversation that never happened.
Reflection
The mistake wasn’t the size of the budget.
It was that I didn’t step back and ask the harder question sooner.
When you avoid the awkward conversation, the awkwardness doesn’t disappear.
It just waits for you in a meeting room, when you least expect it.
If this story resonates, it’s part of a broader leadership conversation I bring to conferences and leadership teams through Awkward Leadership™.
Learn more about my keynote topics here.