Two CEOs retired recently from similar-sized companies. Their departures couldn’t have been more different—and neither could the legacies they left behind.
Michael’s farewell was everything you’d expect from a beloved leader. The board praised his “collaborative leadership style” in glowing terms. His team genuinely mourned his departure. Government officials attended his retirement celebration. By every visible measure, he’d been a success.
Sally’s exit was more muted. The board called her tenure “necessary but difficult.” Several executives had departed during her five years at the helm. Her farewell event was notably subdued compared to the celebration Michael received.
But here’s where the story gets interesting.
Six months after Michael left, his company announced a major restructuring that eliminated the divisions he’d protected for a decade. Millions of dollars in shareholder value evaporated. Within a year, 50% of the workforce was gone.
Six months after Sally left, her company reported record profits from the strategic pivot she’d championed over fierce internal opposition. When an unexpected crisis hit shortly after her departure, the organization adapted with unusual speed and turned the disaster into an opportunity.
The pattern reveals an uncomfortable truth about leadership that most of us would rather not confront.
The Questions Leaders Ask Themselves
Each executive had been asking themselves fundamentally different questions throughout their tenure. These questions were invisible to outsiders and perhaps even unconscious to the leaders themselves. But they had profound effects on performance and organizational capability.
Michael achieved unanimous board approval and high satisfaction scores by proposing only moves people were comfortable with. His instinct was always to adjust proposals until opposition disappeared. Board meetings were harmonious. His team was content. Everyone liked working with him.
Sally generated regular conflict by advocating for positions she might be wrong about—market exits, controversial partnerships, challenging restructuring efforts. She created tension in boardrooms and pushed her team beyond their comfort zones.
Michael was beloved. Sally was respected. And only one of them transformed their company.
In the day-to-day reality of organizational life, we’d all prefer to work with a Michael. It’s just easier. Less stressful. More comfortable. But when you step back and look at the big picture, the Sallys of the world achieve something fundamentally different—they build organizations capable of thriving in uncertain futures.
From Management Excellence to Leadership Impact
The irony is that Michael rose through conventional management success. He delivered immediate results. He worked long hours. He built people’s skills. Everyone appreciated his collaborative style, and he accumulated a long list of admirers throughout his career.
But what made him an excellent manager became deadly when he stepped into the CEO role.
His “nice guy” instinct—so valuable when managing projects and building teams—became a liability when leading organizational transformation. He sought comfort over conflict. He adjusted strategies until opposition disappeared. Board meetings remained harmonious, but no one challenged weak ideas. Everyone was smiling while the company slowly lost its competitive edge.
Only after his retirement did the damage emerge in stark financial terms and workforce devastation.
Sally took a different path. She prepared for C-suite roles deliberately—hiring executive coaches, engaging in intensive leadership development, and training herself to ask a fundamentally different question: “What am I willing to be wrong about?”
This wasn’t just a philosophical exercise. She actively sought out perspectives that challenged her thinking, including using AI tools to stress-test her assumptions and identify blind spots in her reasoning.
As CEO, she pushed for market exits, restructures, and strategic pivots that sparked genuine debate. Board meetings became intellectually rigorous rather than comfortable. Her management team was forced to think independently rather than seek consensus.
When that crisis hit after her departure, the company was ready. Years of her tough choices—the re-engineering projects, the technology integration, the market repositioning—had already built adaptive capacity into the organization’s DNA. The crisis didn’t create team strength. It revealed the resilience her uncomfortable decisions had forged.
What Transformed Sally’s Leadership
A former vice president who worked under Sally explained the shift this way: “Sally never asked what we were willing to do. She told us what she believed we could do, then demanded proof. At first we resisted—some of us vocally. But eventually, we became more than we thought possible. We discovered capabilities we didn’t know we had.”
That insight became the foundation of Sally’s leadership philosophy: people don’t discover their capacity through comfort. They discover it by confronting challenges they initially believe are beyond them.
This realization required Sally to make a conscious decision about what kind of leader she would be. She stopped optimizing for board approval and started advocating for market reality. She stopped asking what people would volunteer and started demanding what they could become.
It wasn’t about being difficult for its own sake. It was about holding up a mirror to the organization’s potential and refusing to settle for the comfortable status quo.
Three Principles for Transformational Leadership
From this fundamental insight, Sally developed three operating principles that guided her leadership decisions:
Advocate for what others won’t see. Not the obvious moves everyone agrees on, but the non-obvious plays that data suggests and comfort resists. This means being willing to be the voice in the room that says, “I know we’ve always done it this way, but here’s what the market is actually telling us.”
Demand what others won’t give. Not what people volunteer to do, but what you genuinely believe they’re capable of becoming. This requires a deep confidence in human potential combined with the courage to ask for more than people think they can deliver.
Test what others won’t risk. Not consensus-driven certainties, but hypotheses you’re willing to be wrong about. This means running controlled experiments with strategic bets, learning from failures, and iterating quickly rather than waiting for perfect information.
These principles aren’t about being contrarian or difficult. They’re about recognizing that transformation—real transformation—requires someone to push beyond the boundaries of organizational comfort.
The Legacy Question
Here’s the question every leader should be asking: Ten years from now, will your successor be building on your legacy or repairing what you avoided?
The companies thriving in 2035 won’t be led by consensus-builders like Michael, despite how beloved they were. They’ll be led by leaders like Sally—people willing to make boards and teams uncomfortable in service of genuine transformation.
This isn’t an abstract theoretical point. It’s playing out in real time across industries. The organizations that thrived through the pandemic weren’t those with the most harmonious cultures—they were those whose leaders had already pushed them to build adaptive capacity through uncomfortable changes.
Your Next Move
This week, starting tomorrow, challenge yourself to do something concrete: Choose one strategic position you believe in but haven’t voiced because it risks discomfort.
Don’t ask yourself if the board will like it. Don’t wonder if your team will resist it. Instead, ask yourself: Am I willing to be wrong about this?
If the answer is yes—if you genuinely believe it’s worth testing even though you might be wrong—then you have your next leadership move.
Because here’s the final uncomfortable truth: the farewell speech that will eventually be given at your retirement is already being written. Every decision you make today, every time you choose comfort or conflict, consensus or transformation, is adding another line to that speech.
Managers chase comfort and celebrate short-term wins. Leaders pursue transformation by demanding more than people thought they could give—and building organizations capable of thriving long after they’re gone.
The question isn’t whether you’ll be liked or loved. The question is whether you’ll be needed—because you built something that couldn’t have existed without your willingness to make people uncomfortable in pursuit of something greater.
What will your legacy be?
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This article is based on a column published in the Jamaica Gleaner.