Francis Wade | How good leaders don’t keep things the same

Two Caribbean CEOs retired recently from similar sized companies. Marcus left with emotional tributes, his board praised his “collaborative leadership”, his team genuinely mourned his departure, and his farewell was attended by three cabinet ministers.

Six months later, the company announced a major restructuring that eliminated the divisions he had protected for a decade. Millions of dollars of shareholder value were lost, and 50 per cent of the workforce was gone a year after that.

Sandra left with mixed reviews; her board called her tenure “necessary but difficult”. Several executives had departed during her five years, and her farewell was notably subdued. However, six months later, the company reported record profits from the strategic pivot she had championed over fierce internal opposition.

The pattern reveals an uncomfortable truth: Each executive had been asking themselves very different questions. They may have been invisible to outsiders, and even unconscious, but they had a powerful effect on performance and corporate functions.

Marcus achieved unanimous board approval and high satisfaction scores by proposing only moves people were comfortable with. Sandra generated regular conflict by advocating for positions she might be wrong about, market exits, controversial partnerships, challenging restructuring efforts.

Marcus was beloved. Sandra was respected. And only one of them (the latter) transformed their company.

In the “small” picture, we would all prefer to work with a Marcus. It is just easier. But in the big picture, the Sandras of the world achieve more.

As a leader looking ahead to 2026, what legacy should you be leaving behind? What key question could you ask yourself?

Contrasting Transitions from Management to Leadership

Marcus rose through conventional management success, delivering immediate results, working long hours, building others’ skills. Everyone appreciated his collaborative style and he had a long list of admirers.

But as CEO, his “nice guy” instinct became deadly. He sought comfort over conflict, adjusting proposals until opposition disappeared. Board meetings were harmonious, his team content, but no one challenged weak ideas. Only after his Runaway Bay retirement did the damage emerge, destroyed shareholder value, a gutted workforce, all while the well-intentioned leader had everyone smiling.

By contrast, Sandra prepared for C Suite roles by hiring coaches, engaging in weekend intensives and training herself to ask, “What am I willing to be wrong about?”

She even used a large language model (LLM) to push the boundaries of her thinking. As CEO, she pushed for market exits, restructures, and pivots that sparked real debate in board meetings and forced her management team to think independently.

So, when a hurricane struck after her departure, the company was ready, her tough choices and re-engineering project launch had already started to build capacity. Now, the organisation could adapt to and turn the disaster into an opportunity to energise its internal change efforts.

The True Leader’s Results

When the hurricane hit, Sandra’s team moved with unusual speed. Years of re-engineering, AI integration, and market testing had built adaptive capacity. The hurricane did not create team strength, it revealed the resilience her uncomfortable decisions had forged.

A former VP explained, “Sandra never asked what we were willing to do. She told us what she believed we could do, then demanded proof. At first we resisted, but eventually we became more than we thought possible”.

That is the insight that transformed Sandra’s leadership. People do not discover their capacity through comfort. They discover it through confronting challenges they initially believe are beyond them.

Sandra made a conscious decision. She stopped optimising for board approval and started advocating for market reality. She stopped asking what people would give and started demanding what they could become.

The three principles that emerged from this insight became her leadership operating system:

• Advocate for what others will not see. Not the obvious moves everyone agrees on, but the non-obvious plays that data suggest and comfort resists.

• Demand what others will not give. Not what people volunteer, but what you believe they are capable of becoming.

• Test what others will not risk. Not consensus driven certainties, but hypotheses you are willing to be wrong about.

As a leader 10 years from now, your successor will either build on your legacy or repair what you avoided. The companies thriving in 2035 will not be led by consensus builders like Marcus, but by Sandras, leaders willing to make boards and teams uncomfortable to drive transformation.

This week, starting on Monday, choose one strategic position you believe in, but have not voiced because it risks discomfort. Do not ask if the board will like it, ask if you are willing to be wrong.

Managers chase comfort. Leaders pursue transformation by demanding more than people thought they could give. Your next decision will define the farewell speech already being written.

Francis Wade is the author of Perfect Time Based Productivity, a keynote speaker and a management consultant. To search his prior columns on productivity, strategy, engagement and business processes, send email to columns@fwconsulting.com.