🏒What the Maple Leafs’ Playoff Defeat Can Tell Us About the Corporate World

🥅From the Ice Rink to the Boardroom: Lessons in Failure, Grace, and Double Standards

I don’t follow sports. But living in Toronto, even I couldn’t escape the Maple Leafs playoff drama. The story unfolded for me in fragments—each conversation offering a curious window into not just hockey, but power, politics, and performance.

First, a friend cheerfully told me the Leafs were up 2–0. But she quickly added, “Don’t get too excited—they haven’t won in decades.” Fifty-seven years, to be exact.

Then came another update: 2–2. This friend made an unusually astute comment: “They get paid per game played. Of course they all want seven games.”
Indeed, players receive compensation for each playoff appearance. And beyond player compensation—sponsors, TV rights, venues—everyone makes more money when there are more games. It was a bold comment from my friend. Every time I’ve dared to hint at conflict of interest (or even light corruption) in sports, I’ve usually been met with indignation.
Not in my sport! Right.

At 3–3, someone else updated me again—this time to complain about players choking under pressure. Some rise. Others collapse. That’s the playoffs.

And finally: 1–6. The Leafs lost. Fans hurled their jerseys onto the ice in protest.
I shared this with my husband—not a Leafs fan, but a former player—and he got visibly annoyed.
“Do you know how many couch critics I’ve heard scream strategy who can’t even skate five feet?”
Fair. He empathized with the players.

Until I asked him:
“How many times could you choke and fail at your job before getting fired?”
That made him pause.

Because here’s the thing.
If a mid-tier hockey player chokes in a high-stakes game, he might not get re-signed.
But if a top-league player fails to perform? He’ll likely be back next year. And the year after that. He’s already too big to cut loose.

That’s what fascinates me—not the sport itself, but the double standard it reveals.
The “too big to fail” mentality—but applied to individuals.

Same in the corporate world.
If a CEO tanks a strategy, they don’t get fired—they eventually (read: after years) “resign to spend more time with their family.”
But an executive two levels down? Miss your numbers?
Bye-bye. Thanks for playing.

Why is that?

Because once you're at the top, failure becomes too embarrassing—and too expensive—to address.
Too many people vouched for you. Too many reputations are invested in your success.
The board doubles down. The coach “stands behind his players.”
Narratives of resilience are spun.
We all nod, pretending this major screw-up was actually…a great learning opportunity.

“We’ll be stronger because of it.”
“This was necessary for our evolution.”

We’ve heard the script. Watch how quickly everyone aligns.

Recently, I was chatting with a Managing Director at a PE firm.
To get the job, he went through 13 interviews and a full case study.
How many interviews do you think his CEO had to go through? I’d bet not 13.
So why is someone four levels below getting more scrutiny?

This isn’t a rant about how high earners “shouldn’t be allowed to be human.” That’s not the point.
People are people—at the top or bottom of the food chain.
But why is compassion and leniency extended more generously upward than downward?
Shouldn’t it be the other way around?

Why do we normalize this?

We’ve seen similar dynamics in other sports.
In tennis, for instance, there’s been a lot of noise around harsh sanctions for low-ranked players—while top stars, like World No. 1 Jannik Sinner, receive far more lenient treatment for similar infractions.
The higher you go, the more grace you seem to be granted.
Why?

So next time you’re hiring an intern, ask yourself:
Who faced more scrutiny—your intern, or you?
And what does that say about the system?

Food for thought.
Peggy

Peggy Van de Plassche is a seasoned advisor with over 20 years of experience in financial services, healthcare, and technology. She specializes in guiding boards and C-suite executives through transformational change, leveraging technology and capital allocation to drive growth and innovation. A founding board member of Invest in Canada, Peggy also brings unique expertise in navigating complex issues and fostering public-private partnerships—key elements in shaping the Future of Business. Her skill set includes strategic leadership, capital allocation, transaction advisory, technology integration, and governance. Notable clients include BMO, CI Financial, HOOPP, OMERS, GreenShield Canada, Nicola Wealth, and Power Financial. For more information, visit peggyvandeplassche.com.