What It Takes To Be A Great CEO

When Chief Executive launched its CEO of the Year award 40 years ago, let’s face it, the job was simpler. CEOs commanded and controlled, made decisions with quarterly updates and could disappear to mountain retreats to think strategically. The biggest technology accelerant of the day? The fax machine.

Today, as we mark four decades of recognizing exceptional leadership, that world feels as antiquated as carbon paper—and that’s before imagining the AI-driven changes of the next decade. So, what makes a CEO great? And how will that change? What skills, abilities, areas of expertise will it take to succeed in the years to come? And why the hell would anyone want to do this, anyway?

We took those questions to a unique group of current and former chief executives who spend a lot of time each year contemplating the craft of being a CEO: a few members of our CEO of the Year selection committee, including Bob Nardelli, the former CEO of Home Depot and Chrysler; Carmine DiSibio, former global CEO of EY; Jeff Sonnenfeld of Yale University, a longtime Chief Executive contributor who has been on our selection committee for 20 years; Fred Hassan, the former CEO of Schering-Plough, and Tom Quinlan, CEO of RR Donnelley. Together, they’ve seen the role evolve from the era of Jack Welch to the age of AI, and their insights map the contradictions that define—and will define—executive leadership in the decades ahead.

The big takeaway from our conversations: CEO success still depends not on nailing some academic playbook or developing some specific set of skills from a manual. Rather, it’s about the circus art of plate spinning, navigating critical tensions—simultaneously—treating them not as either-or choices but as dynamic balancing acts. One-size solutions? Tough to come by. And if you think the gig is hard now, just wait. It gets even harder from here.

“That’s one reason why you keep hearing about CEO turnover—and previously experienced CEOs coming back,” says Hassan. “Because people have a tough time finding CEOs to deal with all the problems that we have. If you just look 20 years from now, that’s only going to get magnified.”

Rate of Learning vs. Rate of Change

The No. 1 challenge facing CEOs, according to our selection committee? The ability to learn and grow faster than the world around you. If you don’t, you risk becoming the bottleneck for your organization. Nardelli is characteristically blunt about it: “You have to grow if you want your business to grow.”

The trick—the requirement—for success here is tough to learn and impossible to fake. The “joy of learning and then sharing that learning with people around you is what really keeps people like me going,” says Hassan, who spent decades leading complex, global organizations at the cutting edge of biology and medicine despite being neither a scientist or doctor. He continues to work in the sector long past the time when many of his peers have traded their briefing decks for golf clubs. It’s simple, he says: Those who don’t find learning “a joy” won’t survive in the corner office of the near-future.

Insulation vs. Engagement

But learning, of course, requires time amid a calendar strained daily by the firefighting and operational oversight needed to run a modern business. Sonnenfeld, who acts as a quiet advisor to many of the world’s top CEOs, says the pull of countless speaking invites, networking opportunities and a rising concern about personal safety are all adding to the burden—more so than at any time in his career. “Nobody wants to talk to anybody else in the company except the CEO,” he says. “So, the CEOs are obliging, and boards are getting concerned about CEOs being worn too thin but also, they’re worried that it’s hard for them to stay engaged with what’s going on.”

One of the biggest changes: the growing pull for the CEO to engage directly with government. Even in mid-market companies, the amount of government involvement in business—promulgated by both parties at the federal and state level—is unprecedented. “In the past, most companies just haven’t had much interaction,” says DiSibio. “They might have that person in Washington, D.C., doing lobbying, but now… I don’t think this is just a Trump situation because now the doors are open to government looking at the government as a company itself and trying to maximize taxpayer money and taking equity stakes and so forth.”

Balance here is going to depend on one of the most underrated but essential CEO skills: calendar management, finding support staff who keep you the right amount engaged without letting you get either swamped or over-insulated from information.

“They can’t let their staff control them,” says Sonnenfeld. “They’ve got to figure out how can they still manage by wandering around, how can they get to know what’s happening in the grassroots level of their own companies and with their owners and all the rest, and not just be a trained seal going around from event to event.”

Trust vs. Control

This speaks to another tricky tension: The organization of the future will require leadership that can sort out decentralized decision-making at unprecedented speed without making break-the-company mistakes. Again, this has always been the case, but the spiraling complexity of business, plus the astounding amount of data available to nearly everyone in a company, will grow in the years to come.

Nardelli sees this strain growing already at the private-equity backed companies he works with. “Everybody wants authority, everybody wants control. It’s a reverse pyramid,” he says. But “few want accountability.”

To strike the right balance, CEOs will need to use technology to help augment their scope of vision and develop organizational structures that are more autonomous and closer to operations and the customer—without sacrificing accountability. It means developing and leading both excellent tech and excellent staff, not one or the other.

“You’re going to need a lot more people who have broad knowledge, who are critical thinkers, who can adapt, who are nimble,” says DiSibio. “And yes, those people will also have to be technology savvy. They will have to understand how technology works, how obviously AI works and so forth. You’re going to have to have a combination. But the actual people skills will be even more important than they have been, partly because then you’re going to have fewer people—and you’re going to need to keep those people.”

Strategy vs. Agility

Meanwhile, the era of three- or five-year strategic plans in leather binders seems as pragmatic as accounting with an abacus. The idea that the calendar year has some mystical bearing on strategy is increasingly passé, with many companies already moving to rolling monthly reprojections and re-budgeting to match fast-changing market and geopolitical conditions. Increasingly autonomous technology and democratized data will make cycles run faster still.

But all that agility will pull against the need for CEOs to provide a constant north star for the organization or else risk endless, vertigo-inducing pivots. Even in this ever-faster era, “it’s good to paint a dream, a future state for the company,” says Hassan. “That’s very important. People still need to see the place where they’re going to go while they deal with the short-term lurches.”

Borrowing from his time in the eye business as chair of Bausch & Lomb, he thinks the path forward is being “multifocal”: to see the business and the landscape in which it operates in the immediate distance, out to the horizon and peripherally—all at the same time. No easy trick.

“We have a tendency in companies to start chasing the big money makers and really pouring on resources on the money makers, which is great,” he says. “But then, there might be new profit streams opening up down the road that you’re going to lose. You have to have a sense of a portfolio manager in terms of still thinking about creating new profit streams for the future. Too many companies fall into the trap of chasing their immediate money makers in a very big way.”

Health vs. The Job

Asked what’s changed most about the CEO job over his career, Quinlan holds up his iPhone. “These devices,” he says. “What Steve Jobs did was cause us to be 24-7. As a result of that, you have to go ahead and treat yourself in a different manner than what you used to because there is no downtime.”

“You have to take care of yourself better,” says Quinlan, even as the phone buzzes and business swirls. That means being a lot more deliberate about getting rest, eating right and working out.

For many big-company CEOs, taking care of themselves can also mean an increasing focus on safety. Among enterprise CEOs, “it used to be 5 percent of them had personal security,” says Sonnenfeld. “And now, way more than half have personal security of some form.” That could end up being the case for mid-market CEOs if the increasingly violent attacks on business leaders—from both the extreme left and right—continue.

Humility vs. Ego

Finally, there’s the challenge that crops up when you least expect it, a growing sense of “I’ve got this” infallibility that all too often accompanies success in the job—and has to be kept in check to succeed. That’s part of what hasn’t changed about being a CEO, says Quinlan—and probably never will.

“Whether you’re leading a Fortune 500 company or your own family business, having the humility, having the ethical leadership, having empathy—that still has to be there,” he says. “Those things have been there. They’re going to continue to be there… You are going to go into the room. You think you know the answer, but if you’ve got a good team around you, they may convince you otherwise. Don’t fight them. They’re probably right.”

At the same time—let’s be honest here—the job will still require what we’d all wink and call “a healthy sense of self.” To be a chief executive, you must get juiced by running and growing a business and have faith you can rally others to feel that way, too. That’s not going to change either.

“It’s the thrill, man,” says Nardelli. “It’s gotta be exhilarating to you to be able to do this. It can’t be low and slow, right? It just cannot be. I mean, people who have that kind of energy or that kind of inquisitiveness or, you know, that competitiveness in them to be able to handle this—that’s what it’s going to take. It just is.”