Carolyn Dewar spent two decades counseling Fortune 100 CEOs as a senior partner at McKinsey and founder of the firm’s CEO Excellence practice. She’s seen a lot and heard a lot (both good and bad) along the way. But one thing she didn’t see—yet many clients asked for—was a handbook to help guide them through all the tricky parts of the CEO job. So she, along with colleagues Scott Keller, Kurt Strovink and Vikram Malhotra, wrote one. AGENDA
A CEO for All Seasons: Mastering the Cycles of Leadership (Scribner) distills research from 83 top-performing CEOs into a stage-by-stage playbook. The premise is simple: The CEO job has distinct seasons—preparing for the role, transitioning in, sustaining momentum and transitioning out—and each requires different capabilities and support.
What makes this relevant for directors is the corollary: boards have distinct roles to play in each season if they want the company and its leader to succeed. “The board plays a critical role in supporting the CEO at every stage,” Dewar says. “Both to support the CEO and to fulfill their fiduciary responsibility to shareholders, that relationship through every phase is critical.”
Here’s what Dewar’s research suggests boards should be doing.
Spring: Build the CEO Bench—Before You Need It
Two to three years before a CEO transition, the best boards are already developing multiple credible candidates. The emphasis on “multiple” matters. “Ideally, you don’t want just one,” Dewar says. “Brad Smith at Intuit talked about how not every horse is good for every course. As a board member, you don’t know what context the company will be in or what kind of leader you’re going to need.”
This means demanding the sitting CEO and CHRO spend serious time developing a slate of candidates. But it also requires boards to resist the common trap of looking for a clone of the current CEO, especially when things are going well.
“The default mode of boards when things are going well is they want to keep the trains running,” Dewar observes. “They think, ‘We’ve had a great run with this person. Let’s find a mini version of them.’ Not only is that not realistic, but it’s unlikely that your company needs the exact same thing for the next five to ten years that they’ve needed for the previous decade.”
Instead, boards should use CEO succession planning as an excuse to have honest, forward-looking strategy conversations. What are the business priorities likely to be in three to five years? Is this growth mode or cost mode? Do we need someone digitally fluent? Someone who can navigate geopolitical complexity? The answers should shape who you’re looking for to run the company.
Dewar’s research points to four capabilities that will matter most for next-generation CEOs: First, constant learning—leaders who see the CEO job as the beginning of their development, not the finish line. Second, comfort making decisions with incomplete information, finding the signal in the noise without analysis paralysis. Third, technical fluency, particularly around AI and emerging technologies. Fourth, stakeholder management—the ability to bring people along rather than command from on high. “These jobs are just too big for any single human being to be the all-knowing CEO,” Dewar says. “You want someone with a demonstrated track record of leading a team to do great things, not just themselves.”
Boards should also look externally, even when they have strong internal candidates. “It’s easier to be more critical of the people who are internal candidates because you know more about them,” Dewar notes. “You can get enamored with the shiny object of someone new, but you actually just don’t know what you don’t know. So have that calibration of what’s out there.”
Summer: Reset the Board
Once you’ve made a hire, the board itself needs a reset. This is particularly true for boards that have worked with the previous CEO for years and developed comfortable, hands-off rhythms. “If you’ve been in smooth sailing mode, that’s a watch-out,” Dewar says. “Obviously, if it’s a crisis and an unplanned transition, you’re probably already in it. But for planned transitions, the board might need to step it up in terms of being more engaged early, asking good questions, making sure that new CEO is off to a good start.”
This doesn’t mean micromanaging. It means helping the new CEO nail their firsts—the moments that will set the tone for their entire tenure. First board meetings matter. So do first earnings calls, first investor presentations, first regulatory meetings, first client visits. “That’s going to set the tone for their tenure and have ripple effects on how your choice of candidate is perceived,” Dewar says. “What can you do to help them really show up well in those first moments?”
The relationship between the CEO and the board chair or lead independent director is disproportionately important. Dewar recommends the chair spend real time with the new CEO early on, getting into a good rhythm and sync. “Your role as chair is to manage the board so the CEO can be doing their job,” she says. This might mean previewing topics with board members, gathering feedback and feeding it back to the CEO or helping evolve the board itself.
At the same time, boards should encourage new CEOs to meet one-onone with each board member, not just hold board meetings. These individual relationships matter. Dewar points to Ajay Banga at Mastercard, who used his board as a consulting service, calling on individual directors with specific expertise. M&A question? Call the board member who’s done deals. Regulatory issue? Call the one who’s navigated Washington. “Helping them build out those relationships and realize what skills are on that board that they can tap into is incredibly important,” Dewar says.
One critical element often overlooked: Boards need to create space for new CEOs to be open and transparent rather than feeling they need to pretend everything’s perfect. The tone set in those first board meetings—whether it’s safe to admit uncertainty or share concerns—will determine whether you get candor or performance art for the rest of the tenure.
Fall: Fight Complacency
This is where boards earn their keep. Three to five years in, when the CEO has started strong and results are good, the biggest risk is complacency. “Everything’s going well,” Dewar says. “Can’t we just keep running the same play? And so how do you have the discipline as a board to really shock the system?”
The best boards don’t wait for crisis. They provoke the CEO and top team to think ahead even while current priorities are still playing out. This might mean taking the board on the road for a listening and learning tour—Piyush Gupta, former CEO of Singapore’s DBS Group, took his board to Silicon Valley to understand where banking technology was heading. It might mean annual strategy offsites where board and CEO push each other’s thinking about what could come next. “They’re on a learning journey together,” Dewar notes.
But boards also need the courage to ask harder questions. “If you were new in the seat, if you came in externally, or worse, if you were an activist—what would you see? What would you be doing differently?” These aren’t antagonistic questions. They’re provocative ones designed to ensure the CEO is thinking boldly enough about the hill they need to climb as an organization.
Michael Dell, who’s been a CEO since age 19 and navigated decades of changing technologies, markets and customer needs, would tell his team to imagine a competitor that in three years would be beating Dell on every dimension—product, service, price. “Now imagine if we were those competitors, what would we be doing now to be ready to outmaneuver Dell in three years?” Dewar says Dell would ask. “Are those the kinds of questions board members are asking?”
This also means giving the CEO grace to make big bets that might create near-term turbulence. “You’re going to need to maybe give your CEO a little bit of time and know that there’s a quarter or two that’s bumpy because they’re making a big investment for the future,” Dewar says. At the same time, you need to be close enough to understand those puts and takes so you’re not surprised.
But beware: Some CEOs constantly chase the latest idea without staying the course. “Sometimes you need to say, ‘No, we placed this bet. We believe in you. Even if there’s some noise in the system, we’re going to stick with it and give it the time we know it needs,’” Dewar says. The board’s job is knowing the difference between strategic persistence and strategic complacency.
At least annually, boards should ask a version of Netflix’s famous question: If you had to rehire this CEO today, would you? “That’s not to have change for change’s sake,” Dewar says. “There’s a lot of cost that comes with disruption. But at least have the conversation: What are the qualities this organization needs of its CEO? Is that what we have?”
Winter: Orchestrate the Handoff
The baton pass from one CEO to the next destroys an estimated trillion dollars in S&P value every year through bad transitions, says Dewar. “There are CEOs who cling to the job because they can’t imagine life beyond it,” she says. “They’re worried about not being relevant, not having purpose.” Helping them develop relationships, hobbies and interests isn’t just kind; it’s protective.
The bigger governance issue: 17 percent of retiring CEOs now stay as executive chair, with an office, coming into work daily. “That’s not great governance,” Dewar says. “It’s really hard on the new CEO. It’s confusing in terms of accountability.” There may be specific reasons to keep someone around for a defined period—you’re mid-merger, for instance—but it should be time-limited and tied to specific work, not a courtesy.
Dewar likes the idea of a “one-way phone” for the new CEO to the outgoing CEO for advice. The person who left shouldn’t be dialing back in multiple levels down, figuring out what’s happening, having opinions. “Warren Buffett said he’s going to go quiet,” Dewar notes. “Should the exiting CEO go quiet? That’s something to address.”
Getting a leadership transition right requires boards to manage both the exit and the entrance. Intuit’s Brad Smith talked about CEO succession with his board 44 times over 11 years—once a quarter. Sometimes it was about bench development, sometimes about timing, says Dewar. “At least every year, step back and ask: Given where the business is going, would we rehire this person today?”
The most delicate conversation involves grooming strong successors who might leave if the transition takes too long. “I’ve seen boards say, ‘We could probably get another few years out of our current CEO. But if we don’t make the call now, we’re going to lose the person who’s going to be CEO for the next decade,’” Dewar says. “Those are very mature conversations to have.”
Asked for a final word of advice for board members, Dewar returns to mindset. “How would you engage with the CEO if you genuinely want the board to be helpful? If you genuinely want it to be a productive, forward-looking, expansive relationship, how honest will you be with one another? How much information will you share?”
The principle, as always, is nose in, hands out. But Dewar pushes boards to ask themselves throughout the journey if they are doing all the things they can to make the CEO wildly successful. “Because that’s great for shareholders and employees and all the constituents,” she says. Not just the CEO.
