Issue #17: Ciao Winter Olympics. Hello Leadership Lessons.
By the time you read this, the Milano-Cortina flame will already be gone.
But the Olympics don't just stop. They conclude. With ceremony. With gratitude. With symbolism that honors what just happened and what happens next — the flame traveling to the next host city, turning an ending into a beginning.
Over the past two weeks, lessons for the boardroom, breakroom, and open office played out in parallel — on the slopes, on the ice, and behind the scenes.
American skier Breezy Johnson stood on the podium holding her downhill gold medal. Moments later, it broke apart in her hands. The hardware failed. Organizers scrambled. Athletes were asked to hand their medals back for repair.
Meanwhile, across the venue, Sidney Crosby wasn’t making headlines for goals. He was being profiled for leadership. For culture. For the ecosystem he built over 20 years. The broadcast didn’t just show his stats — it showed his influence. His mentorship. His ability to make everyone around him better. He didn’t just shine. He strengthened the system that made the shine possible.
The Olympics can teach us something here, through what they get right and what they get spectacularly wrong.
We obsess over Opening Ceremonies — the big launch, the flashy kickoff, the inspirational all-hands deck nobody remembers by Tuesday. Then we ghost the finish and improvise what comes next.
We celebrate individual stars while the systems around them quietly erode. The coaches who developed them. The analysts who built the models. The support teams who absorbed the overflow. No airtime. No budget protection. No recognition. We need more hero shots of the people building the system — not just the ones standing on the podium.
And when something goes wrong, we either bury it in carefully worded memos or let it consume the entire quarter’s narrative. No middle ground. Just silence or self-flagellation.
The Olympics hold excellence and failure in the same arena without collapsing the narrative — by design. Every competition produces winners and losers. Every Games brings together 200+ countries with conflicting values and histories. The system is built to contain that tension. Corporate teams rarely design for that level of complexity.
As the ashes from Milano-Cortina are still warm, let’s look at three patterns worth stealing while they’re still fresh.
Three Lessons Every Leader Should Steal Before the Flame Goes Out
The Olympics don't just give us highlights to watch. They give us systems to study. Every four years, elite performers gather under impossible pressure. Some rise. Some crack. And the difference isn’t always talent — it’s preparation. Infrastructure. Design.
Corporate teams operate under similar constraints. High stakes. Limited time. Ruthless visibility.
As Milano-Cortina closes, three patterns emerge—patterns that separate teams who build cycles from teams who burn through moments. Think of them as the podium finishers in leadership strategy. Not because they're ranked, but because that feels fun and apropos.
🥇 Design the Finish and the Transition — Because Endings Decide Momentum Behavioral science calls it the peak-end rule: people disproportionately remember the emotional high point and the ending of an experience. The Olympic flame doesn't flicker out randomly; it's extinguished with intention, surrounded by ritual, then travels to the next host city. Corporate teams rarely afford themselves that dignity. The ending isn't the epilogue. It's the opening of the next chapter.
🥈 Stars Shine. Systems Sustain. Every Olympic broadcast centers on the athlete, but every medal rests on infrastructure — coaches, analysts, medical staff, and the 3,000 staff plus 18,000 volunteers keeping Milano-Cortina running. Sidney Crosby's two decades of leadership prove it — his legacy isn't the goals, it's the culture he built that made everyone better. In business, if you only reward the podium, you distort what drives performance.
🥉 Excellence and Imperfection Can Coexist Milano-Cortina delivered world records and operational failures in the same fortnight — broken gold medals, ice dance judging that reignited old skepticism, logistical hiccups that required real-time adjustments. The Games continued anyway, because mature systems hold both truths: we're proud of what we achieved, and we see where we must improve. Excellence isn't the absence of flaws; it's naming them without collapsing the narrative.
🧂 Why These Lessons Work
These three lessons aren't borrowed from motivational posters—they're backed by research that's held up for decades across industries, geographies, and team sizes. And the Olympics prove them every two years under global scrutiny. Your team can prove them next quarter without cameras.
The Peak-End Rule Rewrites the Entire Story — Daniel Kahneman won a Nobel Prize proving humans don't evaluate experiences rationally—we judge them by their emotional peak and ending. The middle gets compressed, forgotten. If your project launched brilliantly, performed well for six months, then closed with a chaotic handoff and zero recognition, people remember the chaos, not the excellence. Elite leaders design endings with the same care they design launches because memory isn't fair—it's predictable.
Psychological Safety Multiplies Talent — Research across industries shows the best teams aren't defined by raw talent—they're defined by an environment where people can speak up, challenge ideas, and take risks without career consequences. When that safety exists, performance accelerates. When you only reward the podium, everyone else learns their contributions don't matter. Stars fade. Systems compound.
Acknowledged Gaps Preserve Trust Better Than Perfection — Denise Rousseau's research on psychological contracts reveals something counterintuitive: when expectations shift, what destroys trust isn't the gap—it's the silence. Leaders who openly name where things fell short while celebrating what worked preserve credibility far better than leaders who pretend everything is fine or obsess only over failures. Milano-Cortina had broken medals and controversial disqualifications—and world records and unforgettable performances. Mature systems hold both.
🍴 Try a Bite This Week
You don't need an Olympic-sized budget or a closing ceremony in a stadium to build better habits. But a good coach and a few go-to plays certainly can't hurt. Here's the latter:
🍴 The 30-Minute Closing Ceremony For your next completed project, schedule 30 minutes. Not optional. Calendared. Answer three questions as a team: (1) What worked better than expected? (2) What would we do differently next cycle? (3) Who contributed in ways that didn't make the highlights? Write it down. Share it with stakeholders. Treat the close like you treated the kickoff. Those 30 minutes determine whether people enter the next cycle with energy or exhaustion. Most teams skip it because "we're too busy." That's exactly why you need it.
🍴 The System Audit Pick one high performer on your team. Ask: What invisible infrastructure made their success possible? Coaching? Clear priorities? Psychological safety to fail without blame? Name three specific systems. Then ask the harder question: Are we investing in those systems, or just celebrating the person and hoping they don't leave? If it's the latter, you're building a house of cards. Stars leave. Systems stay. Fund accordingly.
🍴 The "Both/And" Debrief At your next retrospective, put two questions on the same page: "What are we genuinely proud of?" and "Where did we fall short, and what will we change?" Don't bury the second question. Don't let it overshadow the first. Hold both. That's not weakness. That's maturity. And it's what separates teams that improve from teams that repeat the same mistakes with slightly different PowerPoint templates.
💡 A Final Thought
The Olympic flame went out in Verona on February 22. Most people will remember the medals and viral moments. A few will remember the broken hardware.
But the athletes, coaches, and organizers who built those moments? They're already designing 2030.
Your team just finished something hard. Maybe it went spectacularly. Maybe not. How are you closing it? Whom are you celebrating? What are you learning from both the wins and the messes?
Either way, the Olympics gave us three lessons worth stealing.
Don't wait four years—or even four quarters—to use them.
🌶️ Add Your Spice
Which of these three lessons does your team need most right now—better endings, stronger systems, or honest debriefs?
Share it in the comments. Sometimes the best ideas come from leaders willing to try something different.
If this resonated, share it with someone who's building something worth closing well.