413 A CEO for All Seasons: Carolyn Dewar on What Great Leaders Do Differently—From Bold Beginnings to Graceful Exits

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Mahan Tavakoli: \. [00:00:00] Carolyn Doer, welcome back to Partnering Leadership. I am thrilled to have you back with me. 

Carolyn Dewar: Me too. It's fabulous to see you again. It's terrific. Thanks for having me. 

Mahan Tavakoli: Carolyn. Before we got started, I was mentioning to you. As I have said it on LinkedIn posts and to every CEO client that I work  every CEO I've interacted with your book, CEO Excellence is on top of my two be read list to be done list and repeatedly to.

So I am thrilled. We had a conversation back in episode 1 64. We've released it as a best Love episode, but I wanna first start with CEO Excellence. Carolyn, before we go to your new book, the book has done outstandingly well, and you've talked about it to clients and others all around the globe. Would love to know how your views on what you shared in CU Excellence have [00:01:00] evolved since you wrote the book.

Carolyn Dewar: That's a great question. And you're right. In a way it feels like it just happened, but it's also been a couple of years with so many conversations. I think the thing that's been most exciting is similar to what you described is the number of people who found it genuinely helpful, no one wants to write something that sits on a shelf, but I've been really surprised how many people come up to me.

With notes in the margin or they've made their own crib sheet so people are using it as a workbook, which honestly not only is, thrilling and delightful, but also just shows people needed it. I think there was a real craving for that and for this sort of behind the scenes guide, this advice sharing for all of us.

So a lot of it seems to still be resonating and to your question of what have we learned, what's the same and what's different? I think the six big principles are the mindsets. The role of the CEO still hold true, you set strategy, you align your team, you mobilize your organization, you work with your board, your external stakeholders, yourself.

That's still the job. And those [00:02:00] six ring true and are timeless in many ways. I think the degree of difficulty of some of those elements, given what CEOs have been going through the last few years has ebbed and flowed.  The external stakeholder piece, everyone having opinions about your business.

We bounced off the guardrails a little bit in terms of CEOs really engaging in public discourse, taking opinions on social issues. Whoop, that was troubling. They ramped back the other way. We've bounced around on that one. The degree of change and the pace of change obviously hasn't slowed with geopolitics trade policy and.

Climate change, all of the things is still continuing. So if anything, CEOs are just feeling more and more that they need to be intentional, they need to be ahead of it. These jobs are big jobs and the scope scale and pace is not slowing down. So if anything is just even more of a need of, gosh, are these almost super human roles now, and how do we do it well?

Mahan Tavakoli: They really are superhuman roles. But as you mentioned, one of [00:03:00] the things I love about the book is filled with frameworks that can serve as a basis of ongoing thinking and conversation. Carolyn, I find myself rereading the book and referencing it in conversations with CEOs because I find it's.

For me at least. It's not one of those books that I read through and I got it all. I got the point and moved on. There are some valuable books that make a point and then you move on, so I find myself referencing it and going back to it.

Now I want to get another perspective from you on that as well. Is there anything you have changed your mind on or recalibrated based on the book being out there in the world as CEOs are actually reading, thinking about these six mindsets and implementing them? 

Carolyn Dewar: I think it's a great question. The six mindsets have held the test of time,

what it takes to pull them off is a lot of the conversations we've had. So around setting strategy, being bold, what does that really [00:04:00] mean and what does that practically mean in terms of your degrees of freedom as a CEO? , To be fair, it should have been, be bold and be right.

Yeah. 'cause if you were bold and wrong, the performance isn't good, right? Yeah. You also can't be incremental. And every CEO will say you're not gonna have standout performance if you're incremental. But how do you gain that confidence in a world of change and limited information flow sometimes to make these hard calls?

And that's hard to do. And that's been a lot of the conversation, some of the stakeholder pieces, some of the org design pieces. The. Mindset is still there, but how you pull it off has been a real form of the conversation. 

Mahan Tavakoli: It is a lot of paradoxes as well as you were mentioning. You have to be bold, but be right. now I really like the. Next layer of onion that you have peeled with your new book as CEO for all seasons, in that you share these six mindsets and frameworks that [00:05:00] relate to all CEOs now in this new book, you're looking at time and fit, playing a role in making a great CEO as well.

So I would love to know what brought that whole different framework in mind for you. 

Carolyn Dewar: In many ways it feels like a natural extension, because the tenements of being a great CO were still there, but a lot of the questions we were getting and the conversations with CEOs and the counseling was, okay, that's all great, but I'm at this point in my journey.

What does it mean for me? What should I be spending my time on, either disproportionately across the six, or in terms of just being ready and being able to deliver against the role. And both from CEOs themselves, but also leaders who aspire to the role. And that's why there's that first piece of what does it take to get ready?

But increasingly with boards, with heads of hr, for folks who are thinking about that whole cycle we've all seen, . The frictional cost [00:06:00] of getting some of that transition wrong, almost a trillion dollars of value was wiped off outta the s and p each year with CEO transitions that don't work out, so I think everyone's just seeing the value of how do we go along that journey with that leader, with the organization so that they don't have things like sophomore slump and these other things that you hear about that naturally can occur. 

Mahan Tavakoli: , One of the critical points that I get from reading of the book, sort of general points before diving into it is that a lot of times we tend to simplify and think of a great CEO.

It's not that there is a great CEO that time. Space the right fit makes a huge difference. Now, you referenced the fact that in many instances, many boards, Carolyn, including boards that I serve on and I've worked with, spend a lot of time trying to recruit the right CEO, but there isn't that [00:07:00] right fit. So where do you think.

There is the breakage that causes the trillion dollars of loss that you mentioned, and the many struggles that I see the best intentions not resulting in the right CEOs being placed. 

Carolyn Dewar: I think this is so important and it's so important for people who aspire to the role as well as the decision makers like the board who are one of their most fundamental jobs.

Is that higher fire decision of CEO and how do you get it right? I think it's. Treating it as a pure talent decision as opposed to very much linked to the business and the strategy, so the boards that are doing this well are doing this multi-step process of where is the company going, where is it going strategically?

Therefore, what is the work. The next leader is gonna need to do,  is this a growth phase? Is this a contraction? Is it a whole strategic pivot? Are we building a new business? Are we going global? What is it that the businesses are gonna go do in this next era? And then what does that imply for the type of leader we [00:08:00] need?

Both their experience, their knowledge, but also their leadership style, do we need someone who can build consensus? Do we need someone who's gonna be directive? And I think it's too easy for boards to short circuit and say the current person's doing all right, they're doing great, they're retiring.

We just want more of the same, that's the easy or the lazy answer as opposed to say, what do we need going forward? And that may or may not be the same as what you've had, however successful the current CEO is. And it's hard work to really think that through. and Then obviously  to your trillion dollar question point even once you've picked the right person, supporting their transition is another whole piece as well.

Mahan Tavakoli: That transition is really hard. Now, one of the things that you mentioned though, that I've seen a struggle with some boards, Carolyn, is that you mentioned that you need to have a clear strategy in mind and therefore in. Bringing the right CEO, they need to be a fit for that strategy. I've seen quite a few instances where boards have [00:09:00] said, we want to bring in a CEO and let the CEO guide the strategy.

So where is the balance in those two? 

Carolyn Dewar: That's fair. And I almost hesitated in using the word strategy because I think it's an even longer term view that the boards have to take, because ideally, if you have a successful CEO, they're gonna take your company through 1, 2, 3, 4 different s-curves of strategy, maybe over a decade or more, so I wouldn't wanna suggest it's just what has to happen in the next year, but I do think a direction of, Hey, where's the industry growing broadly? What will the next era look like in the broadest sense? I do think that's the role of a board, they talk about being forward looking, having that telescope.

And I think that's part of the board's role as being educated in that way. It doesn't mean that they're gonna dictate the strategy to the CEO, what is it they say? Boards always have to be nos in and hands out on strategy. It's not confusing those two but you do need to know what's the kind of leader we need for this next era.

Mahan Tavakoli: There [00:10:00] is a clarity of directionality from what I'm hearing from you, and then therefore the kind of leadership that will take for that organization. The specifics of the strategy, the new CEO can come in and iterate on that and have new strategy, as you said, few iterations of it over their tenure.

Carolyn Dewar: Absolutely. That's a better clarification. I think that's right. It was Brad Smith, who was the former CEO of Intuit. He loves horse racing, and he was talking about how there's very few triple crown winners, because the idea that the same person or the same horse would be the right pick on multiple tracks that are very different.

 he's quite proud of the fact that he grew. Multiple potential candidates on his slate. Now, ultimately, one was picked that was right for where Intuit needed to go next, but those other candidates, many of them went on to be CEO's, other places, so there is something intrinsic about the leadership quality, but you need to pick a right fit for where you're going.

Mahan Tavakoli: That right fit becomes really important. Now in CEO for all seasons, [00:11:00] you go through seasons of leadership, spring, summer, fall and winter. 

Carolyn Dewar: There was a reason why we picked something that was cyclical, like the seasons . 'cause as we'll talk about, in a way the winter, the fourth season of an outgoing CEO overlaps with season one of the new person coming in. So there's something about that cycle that's important, but essentially the four are the first season, which is spring is before you even get the job.

And some people. Think about that too late, both boards and candidates. It's, all of a sudden we're in a succession, we need to make a pick. Or all of a sudden my interview with the board is in three weeks, can you help me prep? That's not what we're intending for the first season. This is two, three, even more years before you could imagine a transition happening where.

The potential candidates, the sitting CEO, who's developing them, and the board are already starting to think ahead saying, are we building a slate? Do we have people who could be great options? What does that look like? And for the folks who are the potential [00:12:00] future candidate, what's the last mile development that they wanna do?

So that's spring, you're preparing. If anything, it's early spring, it's like the seedlings under the snow. I'm from Canada that are like waiting to burst through. , And then you're in it. It's summer. You are the CEO. Your early days, it's more than a hundred days.

There's a lot of talk of a hundred days, but that first year, 18 months where you're finding your feet, you're setting direction, you're getting your team you're mobilizing and getting that first s-curve of your agenda really up and going. I would say the broadest season is what we call season three, or the autumn or the fall, depending where you are in the world.

And it's this broader thing anywhere between, you're out of the gates, you're not a new CEO anymore, but you're not yet preparing to hand over the reins for successful CEOs. That period can last a while. Sure. Maybe it's only two or three years. It could be 10. And the key in that season is making sure you have that renewal that you don't get stagnant, and then the last season, which we're referring to is winter, [00:13:00] but really is about planting the seeds for the next year and for the next generation, is something that is under thought, there's a lot of thought on the first a hundred days or first year. There's less thought in that last year, especially if it's a planned transition. And how do you wanna be thoughtful, both in terms of leaving the business well? Being graceful in the transition. And there's a personal piece too, of understanding what your next chapter will be, some CEOs find it really hard to move on because they don't know who they'll be beyond that role. So there's some personal work even in that last chapter to hand over well and set the next one up for success. And then the cycle repeats. 

Mahan Tavakoli: So in that cyclical view, as you were talking about it, you started out with Spring and you mentioned some of the preparation that goes into it ahead of time.

Is that primarily with a focus on internal candidates? How does it work when many boards and organizations want to seek someone from outside the organization [00:14:00] for that new spring and energy in. 

Carolyn Dewar: Super. I think it's good governance for any board to always look internal and external, I don't think they should be myopic.

The focus of what we've written about is more from the candidate's point of view or the potential candidate of what you would do to get ready, whether it's in your own organization or maybe you aspire to be a CEO somewhere else, and that's fine too. Just like CEO Excellence, this book is very grounded in the real stories of all the CEOs we interviewed, so these. World-class CEOs and what was the advice of things they wish they had done to make use of that time? It's this beautiful time, and I think some people can get overly focused on the process, what will be the selection process? When will I be interviewed? When will the search firm do my psychometric test?

Whatever it is, and , while we spend some time there, we really focus on the other aspects. Have you really stepped back and reflected, why do you even want to be a CEO? Do you know why you wanna be a CEO? And are those motivations ones that are gonna sustain [00:15:00] you even when the job's hard, because if you're so fixated on getting the job and you haven't realized that the prize for that is you're now in the job, you really need to have thought about what that's gonna look like and why you wanna do it, and what will give you energy. There's last smile. Development that you can do?

Are there exposure experiences you should have? Things you need to learn so that you would be ready to hit the ground started if you were picked, how do you make use of that wind up time to really round yourself out as a leader? 

Mahan Tavakoli: I laugh Carolyn, because it's interesting. A couple of weeks ago I had a CEO tell me I spent most of my career wanting to be the CEO.

Now, I'm not sure this is what I was hoping for and wanted. No, so you're absolutely right. At a certain point, many go-getters aspire to that next step. , Right? Without reflecting on what it means. 

Carolyn Dewar: Oh, absolutely. And I think what we heard loud and clear from the CEOs who've been able to [00:16:00] sustain it over time is the motivation has to be broader than just, I want the title.

Because , that shine wears off pretty darn quick. So , do you have a vision for where you wanna take the organization? Do you wanna be of service to your customers, to your employees? What is it that you're hoping to do while you have this moment in time where you're the custodian of this organization?

Unless it's coming from something deeper it runs out pretty quick. 

Mahan Tavakoli: It is really hard. I respect people who aspire to it, but as you said, there has to be that inner purpose drive and vision that aligns with it. Now, another element that you mentioned in spring is you talk about an unfreezing moment.

So that brief window. Where you can reset expectations and narratives. What do the best CEOs do differently in that brief window, , as you said, it's not specifically a hundred days, it can be six months, it can be that first year, but there is a brief window. What do the best do [00:17:00] differently in that window to set up their spring wealth?

Carolyn Dewar: Absolutely. And really that window is in that transition between spring and summer, it's when either you know you're gonna get the role or you've just received the role where the organization and your other stakeholders, they're expecting some sort of change, and how do you think about and capitalize it, not just as a moment transition for you.

Of the organization and are there things that have been stuck for a long time where you might have a unique window to reset, whether it's talent at the top and really getting your leadership team in place, resetting the ambition, we talk a lot both in CEO excellence and here about a new CEO can decide what is the game we're trying to play,

are we actually even thinking broadly enough about , the company, its purpose, what it's trying to get done? We had this story before from Ajay Bonge MasterCard where a lot of the discussion had been, how do we gain market share? How do we beat Visa or American Express? [00:18:00] And in that window, that unfreezing moment, he and his team came back and said, that's actually the wrong game.

We're not trying to steal market share, which a decade ago in credit card was still like 10% of the world's transactions. Why aren't we going after all of them? Why aren't we trying to kill cash? That was the reframe that he came out with in his unfreezing, and so it expanded the tam. It expanded how we thought about things, and I do think in those early months as a CEO, people are looking for that and there's an opportunity, and if you don't seize it, it's not that you can never do it again, but it's just a lot harder.

People have decided. If you wait a year or two before you're bold, they've said he's not that guy. She's not that person. And it's harder for them to follow . Things have started to lock in about how you lead, what you expect, what pace you set.

So you've gotta seize that moment to really set the. 

Mahan Tavakoli: And that I find is, critical and one of the hardest things to do. I [00:19:00] worked for an outstanding CEO and COO and they kept emphasizing the need, what they called paint the wall moment where. In their analogy, when people walk into the building, they notice something is different or something is better as a result of this new CEO coming in.

Yeah. So there has to be a sense that the organization is on a different trajectory, as you mentioned, potentially a new S-curve. And you have a limited window to be able to do that. 

Carolyn Dewar: Absolutely. We talk about in that summer season, which is this sort of transition piece, nailing your firsts.

These first impressions, your first board meeting, how are you resetting the tone with the board in terms of what you've inherited, the truth of the scenario, as well as how you interact with them. Your first investor day, your first quarterly earnings, your first top team meeting. All of these moments, people are gonna be reading the tea leaves.

Who is this leader? What are they trying to do? What do they stand for? [00:20:00] And whether you're intentional about it or not, they're going to interpret. So you might as well, set the tone you want. 

Mahan Tavakoli: So as you set that tone  what I found is that it becomes hard for CEOs to.

Open feedback and not repeat the previous year, especially people who have been successful have led their organizations to a new S-curve of growth. What ends up happening is a repeat of the previous years. What do the best do differently to be able to go into a new S-curve rather than a repetition of the past?

Carolyn Dewar: I think this is such an important one, the biggest threat in those middle years is your own success because it breeds complacency or you think it's working well. Why do you need to change anything? And so you have to vary. Purposely build in mechanisms to shock the system for you and for the organization.

One of the CEOs we talked about using heart paddles on the organization 'cause the organization can [00:21:00] get complacent as well. They know what they're doing. We're in a good path. And so what does that look like? I think , having some mechanism to learn and listen is key. A lot of CEOs, the really successful ones, are quite specific about how they choose to learn and push their own thinking, depending on their style. Satya Nadella sets aside a day a month. Literally to learn, to read, to have people come in and provoke his thinking, to challenge himself.

Others go to industry events, others engage in round tables with other leaders. There's a bunch of things that CEOs themselves can do so that they are looking ahead, looking around corners, why the organization is operating day to day. 'cause if you imagine they're executing on your current S-curve, you need to be almost a year ahead of them.

Saying what's gonna come after that? What's gonna come after? You touched on an important point, which is even listening within the organization, the other risk is that CEOs become a bit of an echo chamber, they surround themselves with people who they hand pick, who don't wanna deliver bad [00:22:00] news.

You have to find ways to break through that. There's some CEOs we talked to who had say a reverse mentor. They picked someone a couple of levels down in the organization to purposely give them feedback and to say, what are people not telling me? What do I need to know? Now, you have to create real trust to be able to do that, but it's super valuable.

Or maybe there's some other people on your team who can be those eyes and ears for you. Do you sit in the cafeteria and eat with people? Do you walk the shop floor? All of these things to make sure that you're not so far removed from the day to day that you're not seeing the reality of what's happening.

Mahan Tavakoli: It is really hard to do that, Carolyn. , I mentioned I worked with an outstanding CEO, but before he would visit an operation. Everyone knew what they were gonna say, what clients we were going to meet with. Everything was prepped so much. It's orchestrated, absolutely. Yeah.

That the CEO wanted to interact with clients and see people, but they were all preselected who was going to get a chance to interact with the [00:23:00] CEO. So it takes a certain level of intentionality and awareness to push beyond those. Bubbles. , Most of the CEOs I've interacted with are smart people.

They want to dedicate time and they dedicate time to learning and development. If they were asked, they would say, I am very open. I get feedback from everyone. People are open to me. You can't believe it. In our last leadership team meeting so and so said this, or in our last all hands or staff meeting people said that.

But I do also see incredible blind spots, and those blind spots grow as people move up into organization. So what are some additional things, that the best CEOs do to minimize those blind spots and really keep that feedback coming in a way that they are fully aware of what's going on around them.

Carolyn Dewar: Yeah, I love that. As you say, some of it is setting the right tone, but I think you need to be more formal than that. Some CEOs have seen do an edgier approach [00:24:00] where essentially they. Task a team, internal or external, to act as if they're an activist. That's an extreme version. No one wants to have an activist in their stock.

It's never any fun. So how do you get ahead of that? And can you actually give permission? It's a little bit of the devil's advocate or Red team Blue team. Give permission to a small group to say. Go away and crunch the numbers, do the analytics, push on things. If an activist came in today, what would they say?

What would they poke out? What would they look like? And you're giving them permission and almost a stage to say, no, I'm actually expecting you to come back with edgy views. It doesn't take courage. I'm expecting you to do that., leads to really interesting discussion as a leadership team around what are we not seeing?

What are we afraid to face into? What does that look like? That's one technique that's been, , really powerful in a lot of situations. And just continuing to, look for the external world as well. I think this is one where we've seen more and more CEOs engaging with other CEOs and leaders outside of [00:25:00] their industry were the analogy.

Can be really helpful, especially if there's an industry that's maybe farther ahead than you. You saw what happened in regulatory and banking. You wonder if that's coming to yours. How can you learn from that? Any of those things that bring another point of view really challenges thinking.

Mahan Tavakoli: a lot of that comes down to creating the kind of environment, pushing for it. 

Carolyn Dewar: . And making sure you formalize some mechanisms, whether it's, red team, blue team in decisions or devil's advocate, whether it's this activist idea, even your annual strategy review or planning offsite. Are you really being edgy. Are you really having the right discussions or is it a paper exercise?

You can bake it into some of the rhythm of the business to force the challenge? 

Mahan Tavakoli: So that becomes essential for getting that feedback for an ongoing growth and development. I've seen very few CEOs that do it really well for long periods of time. Satya Nadella that you mentioned has done it [00:26:00] superbly well over the years, but at a certain point there is time for transition and.

, At times there's comfort at the CEO level and comfort at the board level.

Carolyn Dewar: Especially if things are going well, right? 

Mahan Tavakoli: Yes. So what would you say are signs that indicate we might want to be thinking about initiating conversations around a transit? 

Carolyn Dewar: , Two thoughts.

One is the great CEOs talk about succession and transition almost from their first year in the job, and so it also takes some of the air out of this being an awkward topic that no one can raise. So Carolyn , 

Mahan Tavakoli: what you just said is a shock to the system.

Of most organizations   I love that perspective. Yeah. It should be a conversation from the very beginning, not a conversation later on where it becomes a lot more threatening. That is such a brilliant point that [00:27:00] makes it a very different conversation when it's an ongoing one that starts at the very beginning of the CEO's tenure.

Carolyn Dewar: Absolutely. And of course it's not at the beginning that you're setting a date saying, here's when I'm out. But it starts with the how I'm gonna structure my team to create feeder roles that will build leaders for the future. How do I think about succession? All of those kinds of things. And then it isn't this sort of elephant in the room that no one can mention, right?

It's just part of your agenda. I do think both for the board and for the CEO at some point, there's some self-reflection questions and a lot of people say it's good to do once a year.  Even if it's just to yourself around, if I put myself in the CEO's shoes for a second. On the business side, do I have an exciting, clear vision of where I'm gonna take the business next? Do I have that? If I don't, maybe that's a hint of why not? Am I not in it? If I do have that vision, what does that imply in terms of the type of leader we'll need? Am I the right one? If it's a big pivot or a whole skillset that I [00:28:00] know I don't have, is that a natural place?

Sometimes there's a natural transition point. You've had a big merger or you've had something where you say, okay, here would be a natural time. There's a consideration of talent and there's been a fair bit of debate in the press on this one where you know if you have ready now successors at some point, if you're still hanging around, you're gonna lose them.

We've seen that play out. That is a risk. And then there's personal considerations, , do I still have the energy? Am I excited or are there things I'm excited for outside of work now? I ready to do that? So I think from them and from the board, that's just a good, healthy check-in to make every once in a while.

And then at some point in a well-planned transition, you do wanna be thoughtful well enough in advance, and at some point communicating to the board. Or have them communicate to you, this is the timing we're thinking about so that you can really do that transition and it's not a shotgun panic.

Mahan Tavakoli: Transition  should be part of the conversation from the [00:29:00] beginning and ongoing. Not that there's a specific date set for it, but it is not a conversation that you get into because something has gone wrong, gone wrong, 

or we are about to lose a specific talented person. Because that changes the dynamics of the conversation and the kind of thinking it takes to bring on the new CEO. Now, that said Carolyn, there are lots of high profile organizations that don't do this well at the board level and with the CEO.

So what do you think gets in the way in addition to some of the processes that you've mentioned of making sure that the board. Is able to develop and recruit the right CEO for the organization. 

Carolyn Dewar: I think developing  and recruiting and selection is a piece of it, and we should, we'll talk about that.

I think there's other pieces of doing it well as well. CEOs in their last [00:30:00] year. They're worried about their legacy. They wanna finish strong, they wanna go out. The shadow side of that, if I'm very plain, is you see CEOs who, squeeze every last cent out of the last quarterly earnings so that they look really good in their last quarter, and they leave the new person with a hole to dig out of, or they make a huge strategic commitment in the last.

Months now their pre, you know, their new person is stuck with, those kinds of things are unhelpful gifts to leave. The helpful ones are, maybe there's a long overdue talent decision that's really hard, that's much easier for you as the outgoing CEO to take care of than to saddle the new person or a budget decision.

The graceful CEOs. Do the helpful parting gifts, not the ones that , lock the hands of the new person and they really are helpful in that transition. The other sort of blind spot we see sometimes it's almost 20% of public company CEOs now when they retire in good standing, move [00:31:00] into an executive chair role.

I actually think it's really challenging governance, especially if it's open-ended. There's CEOs where literally they still come, retired CEOs still come to work every day. They don't even move out of their office. They start attending the leadership meetings also not helpful. Right now there are a time and a place where exec chair can make sense as a transition role, but it has to have a defined time period.

It has to be clear what that person is supposed to be doing with their time. I love the phrase that someone used it. It's a one-way phone, the new CEO can call them for advice, but the phone doesn't work the other way. And so there's a lot about the transition. And when you think about some of the recent ones that have gone not so well, or where there's been a boomerang, CEO who's left and then had to come back, some of these things weren't handled that well.

And so selection is a piece , but all the other things I don't think are talked about enough. 

Mahan Tavakoli: I think all of those are really important and I tease and make fun of and joke about [00:32:00] CEOs that end up bringing in a successor and then finding out that the successor was not good enough and then come back to become CEOs.

There's something wrong with the recruitment selection and development process of that new CEO if. That's where you are, have to come back to the organization. So this is a really important thing to get right now. One of the other things that I really appreciate you going into in the book is this ongoing reinvention that CEOs go through while in the role, in addition to some of the learning that you talked about and the feedback, what do CEOs do to reinvent themselves while in the role?

Carolyn Dewar: I think it's a great question. We've talked about some of them in terms of the learning mindset, that struck us across all the interviews with these CEOs. You would imagine these folks who've been in role for a while are doing really well. They'd probably be [00:33:00] pretty confident. Yet there was a humility.

Honestly is surprising in some of these legends that we talk to, and especially with the pace of change, an acknowledgement that they constantly had to be learning and being very specific about That's a piece of it. I do think there's something about their own personal operating model and managing the sustainability of this job.

Literally. Are you sleeping? Are you exercising? Are you doing the things that aren't about, fluffy, nice? Let's not go work hard things. But if you imagine one of your biggest assets is your brain and your ability to make great decisions, it's actually poor asset management to not be taking care of.

The singular brain that's making the biggest calls in the company, and so are you doing those things? I think that really matters. And I worry a little bit about some of the dialogue of, 24 7 and we should all be working more. I think that's true,, but you need to be smart and you need moments of [00:34:00] recovery.

We talk about multiple sprints, because it's not just a sprint. This is a long haul job. It's also not a marathon. 'cause you can't wait till the end to show results. And so what are these moments where you surge with your team to accomplish something great and then you have a moment of recovery to celebrate, to pause, to recoup, okay, now we're ready to go again.

I think all of those things are important, not just for the CEO, but frankly they're role modeling for their team as well. 

Mahan Tavakoli: exhausting just thinking about it, Carolyn, but as you make the point, I see it, there is that need for , the sprints and ongoing refresh as well, because the ones that are in it have incredible demands and stress placed on them from all kinds of stakeholders all around them. Therefore, need to be able to prioritize some of the balancing, some of the refresh in order to be able to contribute back well to their teams and organization.

Carolyn Dewar: [00:35:00] Absolutely, and it came back to something I think we talked about in our last conversation, which is the CEO can only do the work. Only the CEO can do, if anything can be delegated, if anything can be passed on, because for the work that only the CEO can do, because you have the purview that no one else has.

That alone is enough to more than fill a day. So if you're taking on even more, that's just a problem. It was funny, I'm smiling 'cause yesterday I was reminded of, there was an HBR article from 1999, which is hard to think that it's still relevant about who's got the monkey. I dunno if you remember.

Yes. It's a classic, right? The monkey on the back. And I do think, especially early tenure CEOs, it's easy to wanna take it all on yourself because you feel that. And unless you have a team in place where you're getting leverage, if you're finding yourself digging into someone else's job, at some point you have the wrong person in that role.

And you need to make those hard calls. 

Mahan Tavakoli: , It is really hard. And that is a relevant point and [00:36:00] article and a challenge that I continually see where, as you mentioned, the CEO is taking on more than what only the CEO can do. That's great advice. Now, one of the things that I would love to get your thoughts on, Carolyn, is that.

 Now AI is playing a role, not just in terms of organizational effectiveness and strategy. I've been fascinated that there are few CEOs that have used AI avatars to make themselves or a version of themselves available to all employees where they can have conversations with them. Huh? Would love to get your thoughts on.

As we are transitioning into a world where digital avatars can be trained with all of our content, all of our thinking, where do you see that playing a role? The C-suite with the CEO and the [00:37:00] board.

Carolyn Dewar: That's, I think that's fascinating. I've thought more about AI broadly than avatars specifically.

I think it's a fascinating concept. I worry a little bit about the human connection. I still believe I'm old school, that there's no substitute from people hearing from their leader and knowing that their leader is human and gets them and sees the reality. But I do think CEOs are. Served to start getting smart about ai, not just for their company, but for themselves and their own operating model.

How are they using it, essentially as a, coach in their pocket? Dedicated business analyst, someone they can ask questions to, someone they can test thinking with. There's some fascinating use cases there that we're gonna explore over time in this world where the demands of the job are bigger than what one human can do, is it maybe your sidekick and I get more excited about the idea of it as your thought partner and sidekick than your avatar replacement.

But it's an interesting concept. 

Mahan Tavakoli: I love that perspective. Use it to augment, not to replace. [00:38:00] Yeah. In that a part of the value. CEOs, in my view, bring is that human connection and that human inspiration, which goes back to what you mentioned, why the CEO also needs to have a purpose that they want to achieve through this role.

If they do, then it is important to be able to, in a human way, connect that with the employees, with their team, which becomes essential. So use it as. To augment your thinking and tool as a cognitive sparring partner, not necessarily automation and replacement. 

Carolyn Dewar: We'll see. The world is changing so quickly, but that's where I'm at today.

Mahan Tavakoli: So Carolyn, now as you've written this book, you're going out with it, if we have a conversation a year from now. I have no doubt this will be another bestseller . What is the difference you are hoping a CEO for all seasons will make? As you do, [00:39:00] talks all around the world and interact with McKinsey clients.

What is the one thing you're hoping CEOs will tell you? It has helped them do differently or one way it has helped them think differently. 

Carolyn Dewar: Sure. And maybe two lenses. One is for the co themselves, and then one more broadly, my mind goes to the CEOs themselves first. These are incredibly lonely roles.

There's been lots of talk about why that's lonely. I still love Satya Nadal's answer, which is, it's an information asymmetry problem. No one else sees all the things that you see,  I love the idea that people would feel they have a coach, a trainer, a playbook in their pocket that's been there, done that with advice from some of the best CEOs in the world that they can flip to in the moment.

As you say, it might not be a read through from beginning to end. It's a guidebook that you can flip to in the moment when you're struggling with something that makes you feel less alone and that, frankly, share some of the best [00:40:00] practices that we know work so that people don't need to be recreating. So inefficient for everyone to be rediscovering and recreating themselves.

So that's my hope for individual leaders, that they feel successful supported and less alone, and that we can share all of this. I think broadly when we step back a world where we have CEOs that are more successful, that are better prepared in season one, that the transition goes well and we don't lose a lot of value and frictional cost of the churn of getting it wrong.

We have folks who then. Don't get complacent and they're charting exciting s-curves and then they hand over with grace and are excited about their life beyond. I think that serves all of us, all of the constituents, the hundreds of thousands of employees that report to them, the customers they serve, their investors and the communities they operate in because the world needs great leaders.

That's something we've really experienced time and again. Increasingly, we're looking to our business leaders to provide some of that steady [00:41:00] guidance. And so it serves us all to have folks who are doing these really difficult jobs.

Mahan Tavakoli: We do need outstanding leaders and the world has continually become more complex.. Yeah. So  we do need great CEOs.

And great leaders who can effectively lead their teams and organizations through this greater complexity. That said, your books, CEO Excellence, and now the brand new CEO for all seasons. Our outstanding reads and in my view, books to be read and reread, highlighted, as you mentioned, notes on the side so we can do things differently because there's a huge difference between knowing what we're supposed to say and do and being able to do it.

Where would you send the audience, Carolyn, to find out more about the books and also follow your outstanding writing and [00:42:00] work? 

Carolyn Dewar: First of all, thank you for saying that. I know, especially for you as someone who spends so much time with CEOs, hearing that it's practical on the ground means the world, and I think that's the goal of all of this.

If you type in a CEO for all seasons in McKinsey, it's gonna get you to our landing page that gives you all kinds of more content. There's video interviews with some of the world's best CEOs. There's articles, there's all kinds of things. It also can lead you to the book itself. And then , you and I even together , try and have fun conversations online that are timely, right on LinkedIn of how is this playing out, what are people struggling with?

And that's invaluable input to us, but also hopefully for folks who are in these roles or broadly leadership. I think 90% of this applies to anyone in a leadership role. So that's the goal. 

Mahan Tavakoli: One of the things you mentioned about some of the top performing CEOs is reflective of you. Carolyn, you said you can't believe it. You talk to some of these top CEOs. [00:43:00] They are so humble and genuinely curious. One of the things I've appreciated both in reading your book and then in ongoing engagements on LinkedIn and elsewhere.

Is your genuine humility and curiosity. So I really appreciate having you back on partnering, leadership, talking this time about a CEO for all seasons. Thank you so much, Carolyn. Doer, 

Carolyn Dewar: thank you so much. It's been wonderful to chat. Always a joy.