Leadership has never happened under perfect conditions. But today's leaders are being asked to navigate an unusual number of pressures at once: AI is transforming how work gets done, organizations are restructuring, trust is harder to earn and every consequential decision can unfold in public.

There is no shortage of theories about how to lead through it. But some of the most useful lessons come from people who have actually had to do it.

Across business, government, sports and media, leaders have faced very different versions of the same challenge: how do you move people forward when the path itself is changing? Their experiences point to some of the leadership skills that matter most now.

Leading Through Transformation Without Losing the Organization

Change is easy to announce. Getting thousands of people to move with it is considerably harder.

KATHRYN McLAY has experienced that challenge at extraordinary scale. As President and CEO of Walmart International and, previously, President and CEO of Sam's Club, she has led hundreds of thousands of associates through periods of significant transformation. Her experience illustrates something that can get lost in conversations about disruption: organizations don't transform. People do.

BILL McDERMOTT has spent his career leading technology companies through similarly consequential periods of change. Now Chairman and CEO of ServiceNow, and previously CEO of SAP, McDermott has operated at the forefront of successive technological shifts. As AI reshapes nearly every industry, his experience offers a lesson in making ambitious change feel like a direction people can move toward rather than something happening to them.

EMMA GREDE offers another perspective on leading through change: building organizations designed to challenge the status quo from the beginning. As a founder and entrepreneur behind brands including Good American, Grede has helped turn new ideas about consumers, representation and culture into businesses built for scale.

Whether transforming an institution or building something new, the challenge is similar: leaders have to give people a reason to move toward a future that doesn't exist yet.

Making Decisions When There Isn't a Perfect Answer

The decisions that define leaders rarely arrive with complete information.

Former Canadian Prime Minister JUSTIN TRUDEAU spent a decade making decisions in an environment where economic realities, public opinion, international relationships and competing constituencies could all pull in different directions. Former U.S. Treasury Secretary JACK LEW has faced his own version of consequential decision-making across government, diplomacy and finance.

But this challenge isn't limited to government. ALLISON ELLSWORTH built poppi from a kitchen experiment into one of the most recognizable brands in its category, making the kinds of bets every entrepreneur confronts before the outcome is obvious.

Different stakes, different institutions, same fundamental problem: at some point, leaders have to make the call before they can know whether it was the right one.

Building a Culture That Performs Under Pressure

In sports, culture isn't an abstract corporate value. Eventually, the scoreboard tells you whether it's working.

That makes championship teams particularly interesting laboratories for leadership.

GENO AURIEMMA has built one of the most successful programs in the history of college basketball, sustaining excellence even as players, expectations and the sport itself have changed. CHERYL REEVE, one of the most accomplished coaches in professional basketball, has repeatedly turned talent into championship teams, offering a powerful example of how leaders establish standards that hold up under pressure. And at UCLA, CORI CLOSE has built her program around developing people as deliberately as players.

Their careers make something clear that applies far beyond sports: culture isn't what a leader says a team values. It's what gets reinforced every day, especially when expectations are highest.

The best leaders find ways to demand more from people while giving them a reason to believe in what they're building together.

Leading When Everyone Can See You

Leadership has become increasingly public.

CEOs now communicate not only with employees and boards, but with customers, investors and audiences watching their decisions unfold in real time. Political leaders face the same scrutiny at even greater scale. Media leaders operate in an environment where trust itself can become part of the story.

GINNI ROMETTY led IBM through a period of enormous technological and organizational change while managing the expectations that come with one of the world's most recognizable companies. ANNA WINTOUR has spent decades leading at the center of a highly visible industry where influence, judgment and cultural change constantly intersect. And WENDY McMAHON, having led major media organizations through periods of extraordinary disruption, brings the perspective of someone for whom maintaining public trust was inseparable from leading the organization itself.

Today's leaders don't have the luxury of separating leadership from trust.

Communication Is Becoming a Core Leadership Competency

A leader can have the right strategy and still fail if nobody understands where they're going.

That makes communication more than a soft skill. Increasingly, it's part of the job itself.

SUZY WELCH has spent years studying careers, organizations and the choices people make about work, offering a perspective on what employees increasingly expect from those who lead them. Behavioral scientist LESLIE JOHN studies disclosure, communication and trust, revealing how seemingly small choices about what we share can shape how other people perceive and connect with us.

KATIE COURIC has spent her career doing something leaders in every field now have to do: take complicated ideas, understand what matters and communicate them in a way people will actually hear.

Clarity doesn't replace strategy. It is how strategy becomes shared

There Is No Single Model for Leadership

The CEO, the championship coach, the entrepreneur, the former head of state and the journalist have very different jobs. The environments they lead in are different, too.

And perhaps that's the point.

There may no longer be one definition of a great leader. But look across the experiences of people who have actually had to lead when the stakes were real, and certain disciplines keep appearing: judgment when the answer isn't obvious, adaptability when circumstances change, communication when people need clarity and trust when others are deciding whether to follow.

The circumstances of leadership keep changing. The work of earning people's confidence does not.

Continue the Conversation

The Harry Walker Agency represents leaders and thinkers who have built organizations, transformed industries, coached championship teams and made consequential decisions on the world's biggest stages. Their experiences offer more than theories about leadership. They offer lessons earned by doing it.

Explore more Leadership & Management Speakers >>