Carolyn Dewar shares insights from top CEOs on how to master each season of your leadership career.
You’ll Learn
- How to avoid the nearly universal blind spot of leaders
- How to thrive in any leadership role
- How to nail your first impressions and set the right tone
About Carolyn
Carolyn Dewar is a senior partner in McKinsey’s San Francisco office. She coleads McKinsey’s CEO Excellence service line, advising many Fortune 100 CEOs how to maximize their effectiveness and lead their organizations through pivotal moments. She has published more than 30 articles in the Harvard Business Review and McKinsey Quarterly and is a frequent keynote speaker. She is also the founder of and faculty member for many of McKinsey’s client master classes for sitting CEOs and those preparing for the role.
- Book: A CEO for All Seasons: Mastering the Cycles of Leadership
- LinkedIn: Carolyn Dewar
- Corporate Profile: McKinsey & Company
Resources Mentioned
- Book: Born a Crime: Stories from a South African Childhood (One World Essentials) by Trevor Noah
- Past episode: 1066: How to Thrive When Your Resilience Runs Out with Dr. Tasha Eurich
Thank you, Sponsors!
- Strawberry.me. Claim your $50 credit and build momentum in your career with Strawberry.me/Awesome
- Vanguard. Give your clients consistent results year in and year out with vanguard.com/AUDIO
- Quince. Get free shipping and 365-day returns on your order with Quince.com/Awesome
Carolyn Dewar Transcript
Pete Mockaitis
Carolyn, welcome!
Carolyn Dewar
It’s great to be here. Thanks for having me.
Pete Mockaitis
Well, thank you. I’m excited to be chatting about CEOs. You and your co-authors studied 200 of them to write this book, A CEO for All Seasons. Tell us, how was scheduling all those interviews? That must’ve been a nightmare.
Carolyn Dewar
It was quite busy. These are very, very busy people. So, certainly, we were a taker on the calendars. Whenever they offered, we said, “Great,” and we made it work.
Pete Mockaitis
Well, I’d love to hear, so engaging with all these folks, any really fascinating or surprising discoveries bubbling up here?
Carolyn Dewar
Oh, my goodness. I mean, there’s so many we can dive in. First of all, it wasn’t just 200 CEOs. We tried to find the best 200 CEOs, and there’s lots of questions around what makes best, but we wanted to take advice from people who were awesome at their job, right, which is, I love the whole ethos of the conversations you have.
And so, we were looking at these folks who’d all been in role for at least six years, had been outperforming and doing really, really well, and there were so many surprises when we talked to them. I mean, we can dig in. I guess one would be, you would expect folks who are so successful like that, you would wonder if maybe they’re a little arrogant, maybe they think they know everything.
It turns out the longer they were in role and the more successful they were, the really good ones actually realized that they still needed to be learning. And so, they were curious, they asked questions, they were always trying to find new information. Maybe that’s why they’ve ended up doing so well, but they never stopped learning and growing and trying to get even better.
Pete Mockaitis
Well, beautiful. I mean, we’re all about that here. Well, since you brought it up, I have to ask, your research revealed that the average CEO, does that mean not the super high performers, or does that mean a representative group of your CEOs scored themselves higher than their boards and their direct reports? Can you dig into that a little bit? Are you suggesting that the top CEOs don’t fall for that or this is prevalent with this grouping as well?
Carolyn Dewar
So that research and survey was sent out to all CEOs, all CEOs, in general. And we were asking them to assess themselves around the elements of the role and how well they did. And it’s fascinating. It’s the only time I’ve done research where the answer was 100% of the CEOs that we surveyed scored themselves higher than the direct reports scored those CEOs, 100%, which is fascinating, right?
And it says, gosh, when you’re in these roles, I don’t think it’s that you suddenly think you’re amazing. I think a lot of people stop telling you the truth. You run the risk of being in a bit of an echo chamber. Are people really giving you input on whether things are going well, how it’s landing? And so, for all CEOs at all 10 years, it’s really important to think about, “How do you break through that echo chamber and make sure you’re listening and learning and growing?”
And the CEOs, the high performers we looked at, though, they didn’t hit that sophomore slump that you see from other CEOs, where they got off to a good start and then it whittles away. These are all folks that continue to go from strength to strength. And that’s why we wanted to really understood what they did differently.
Pete Mockaitis
Well, boy, I think we could chat for half an hour about this alone because, yes, that is striking whenever 100% of anything happens in this kind of a research, that is wild. And we had Dr. Tasha Eurich on the show talking about how we’re not as self-aware as we think, and here’s a dimension. When you say score themselves, could you give us an example? Like, score them on like what kind of dimensions or what kind of questions are we talking about this scoring?
Carolyn Dewar
So, it’s very much grounded in research we’ve done on, “What is the CEO role and what does it mean to do it well?” So, there’s six parts of the role. You set direction, you align your organization, manage your team, your board, external stakeholders and yourself. And on each of those, we have a view of “What does really great look like?” And we had each of the CEOs score themselves on how well they thought they were doing. We had their direct reports do it and we had their boards do it.
Now it’s interesting. For new CEOs, the board often actually thinks they’re doing a better job than the newbie does, which maybe isn’t a surprise because you’re new, you’re a little bit nervous, and you’re probably at the peak of the honeymoon period where the board thinks you’re great because they just picked you, so they obviously think you’re great.
So, there’s these different moments where the self-awareness flexes and flows. But the most important thing we were trying to figure out is, “What are those blind spots? And what do you do to make sure that you get ahead of them and you don’t fall into those traps?”
Pete Mockaitis
Well, why don’t we just go right there? What are some of the most common blind spots?
Carolyn Dewar
Well, the reason we anchored this work in the four seasons of the CEO is it turns out a third of CEOs don’t even make it past three years. So, they get out of their gates and they stumble. And I think it was 68% of CEOs, who were experienced that we talked to, said the job actually wasn’t what they thought it was when they started, and they weren’t maybe as well prepared as they thought they were.
And all of that got us to thinking, “Gosh, isn’t it important to help people understand each step of the job, right? When you’re a candidate, when you’re new, in your middle years, and then as you’re thinking about finishing strong and exiting, there’s different expectations at each of those stages that your investors have, your employees have, your organization has, and what do you need to be doing as a CEO in each of those?
And so, we kind of went through and said, “What do the greats do? What are the blind spots at each of those stages?” So happy to dig in on any of those, but that’s the four seasons, essentially, is this cycle that CEOs and companies go through.
Pete Mockaitis
Well, yes, we are going to hit the four seasons. That’s a clever little metaphor. It reminds me of the “Gilmore Girls,” spring, summer, fall, and winter. But perhaps, first, could you share with us, what is the biggest mismatch or surprise CEOs have in terms of, “Oh, wait, this is the job?”
Carolyn Dewar
I think when you dig into that 68% who say, “Gosh, the job was not what I thought it was,” if I think about these six aspects of the job, the first three, anyone with a big role has done. You’ve set direction and strategy, you’ve figured out how to align your organization, your talent, your culture, and you’ve worked with the team. So, I think on those three elements, CEOs are like, “Well, yes, it’s new, it’s bigger scale, it’s more complicated, but I’ve done it before.”
The other three parts of the job is the ones they feel least prepared for. Suddenly, you’re engaging with the board, you’re working with your board, you have 12 bosses. It’s the only job where you actually have 12 bosses. All the external stakeholders, you’re suddenly the public face of the company. There’s a million people with opinions externally on what you should be doing. Especially in the last few years, we’ve seen a lot of CEOs struggle with, “What issues do you get involved in? How do you interact with government and regulators and all these things?”
And then the last part is your own personal operating model, which is how you spend your time, how you show up as a leader. I think a lot of CEOs are just overwhelmed in the first year about the magnitude of the role. There is just endless demands on your time. And it’s up to you to be really quite ruthless about, “What are those critical few things that if you don’t do them, no one else can, right?”
The mindset on that is “Do what only you can do.” What’s the work that only the CEO can do? Because, frankly, that alone is going to fill your whole week. And so, how do you make sure all the other things that can clutter your calendar, you find another way to manage?
Pete Mockaitis
Yes, that notion, “Do what you alone can do” is a nice mantra there. And so, what are some of the most insightful questions these ruthless prioritize-rs are using to identify and surface and truly say, “Yes, indeed, only I can do this”?
Carolyn Dewar
It is one of the questions people struggle with the most, right, is having that clarity. I think it needs to start with a real grounding in, “What are the priorities of the business?” So, what are the two, three, four big moves, big priorities, big strategic shifts that you’re going to drive that will create value? And if they’re at that level of importance, they probably need some involvement from you. So, you should be spending time on really driving the priorities that matter.
I think leaders also recognize they need to shift into a mode where they’re not only the ones, they can’t be doing everything anymore. They need to lead through others, lead through leaders. And so, how do you get your leadership team working really well, not just with the right bums in seats and the right people, but actually aligned on the vision, making decisions well together so that they could make great decisions even if you weren’t in the room, right? That’s another big piece.
And then there’s some invisible work. There’s kind of the running the company. But there’s invisible work that, while the company is running, you need to be the one that pops your head up and looks around corners, and sort of says, “Well, what are the trends that are coming next? What could be some of the threats coming? What do we need to be thinking about for years two and three beyond this?” That’s your job, too.
And so, recognizing these pieces that, if it’s not for the CEO, no one else can set that kind of clarity. And then, honestly, working with your EA or your chief of staff to be really disciplined about, “Are you actually spending time on the things you said you would? Or, are you letting a bunch of firefighting creep into your calendar, which can just overwhelm?”
Pete Mockaitis
Well, you mentioned working with your EA, and I want to get your hot take on this. Most of our listeners are not CEOs. But I’m curious, having such a deep inside perspective of CEOs and what makes them great, what are some of your top recommendations for, when a professional in a more junior role is interacting with the CEO or a senior leader, given all you know, how can we be maximally helpful, insightful, differentiated in how we interface with these executives?
Carolyn Dewar
I think it’s a great opportunity to practice kind of putting on that CEO hat, right, because the one thing about the CEO job is they’re the only one that sees all the pieces. Everyone sees a part of the elephant. They’re the only one that kind of sees it all together.
So, the more you can try and put yourself in their shoes, and say, “If I was solving not just for my team or my function or my business or my geography, and I was actually solving what’s right for the company, would I think about this differently? Would I pose different questions? Would I answer them differently?”
Because the CEO job, they talk about it being lonely, and part of it is they’re the only ones sometimes trying to take that high-level view. Any of us can do that. Any of us can try and put ourselves in those shoes, and say, “Okay, if I’m thinking like a CEO, is this keeping me up at night? Is it really about, is the enemy me versus my other business unit I’m battling with? Or, is there kind of a bigger fight we’re fighting out there and we need to be working together?”
I think having that enterprise mindset is a big deal. It was Brad Smith, who was the CEO of Intuit, he talks about a sports jersey. Now I’m not a great sports person, but the thing that appealed to me is, “Your team’s name is on the front and your individual name is on the back. And he says, “When you’re coming to those situations, are you coming, representing and doing what’s right for the team? Or, are you trying to just optimize for your piece of the business, your piece?”
I think that’s the biggest shift in terms of thinking like a CEO and working with them is you got to put yourself in that enterprise-mindset view.
Pete Mockaitis
Well, that’s so helpful. And it’s funny because, in a way, it seems like, “Yes, of course, they would appreciate that.” And yet, boy, there’s so much working against that.
Carolyn Dewar
It just drags you down.
Pete Mockaitis
In terms of, “Okay, there’s urgency, there’s complexity, there’s too much to do. And then there’s, frankly, you know, my goals, my KPIs, what shows up in my performance management, reviews and process. It’s, like, I don’t so much get credit, if you will, for thinking about that and raising that.” And so, but call me an optimist, I think that just makes that an even more delightful opportunity in terms of, if you go there, boy, what a breath of fresh air.
Carolyn Dewar
You’re refreshing when someone does it.
Pete Mockaitis
Yeah. It’s like, “Wow, that’s so thoughtful.” It’s like, “Hey, we’re making this but, boy, it seems like this is going to be a nightmare for the sales team to be able to gather all of these requirements from their customers when they’re trying to win them over at the same time. Is there, hopefully, some easy process by which we’re collecting that information?” Like, “Oh, none of us have thought about that yet. Thank you for bringing that up. That’s huge.”
Carolyn Dewar
Exactly. I think it’s huge, right? And it differentiates yourself as a leader and you stand out, but it’s also just the right thing to do for our customers and our clients.
Pete Mockaitis
Certainly. Well, let’s hear this metaphor. So, we got the four seasons: spring, stepping up, preparing for the role; summer, starting strong, leading with impact; fall, staying ahead, sustaining momentum; and winter, sending it forward, succession planning, lasting legacy, sorts of things. Could you perhaps share with us a fun story and perhaps a best and worst practice that you see among CEOs within each of these four seasons?
Carolyn Dewar
Yeah, absolutely. We can start with the first one, which is really about when you’re preparing for the role, and it could be the CEO role or, honestly, any next big job that you aspire to. What do you do to get ready? I think a lot of folks fixate on, “What do I have to do to get the job?” and they don’t think about what it means to be great at the job.
It may be an unrelated but interesting analogy. There are some people who are focused on having a wedding and they forget that the prize is now you’re married to this person. It’s the same kind of mindset. You have to think about the long game.
And so, the candidates that do really well, take time in the two, three years leading up to it, really thinking about two things. One, “Why would I even want that bigger job?” Because if the answer is just, “Because I deserve it,” or, “It’s my time,” or, “I want a promotion,” that’s not going to give you the energy to sustain it when those jobs get really hard.
You’ve got to be motivated by something else. Is it that you have an exciting vision for what you’ll do in that role? You’re excited by a mandate you could set, or a customer journey you could create, or some value you could create, or the people you’re going to help to be successful.
You need some bigger purpose in taking on the role or, frankly, the honeymoon period weighs out pretty quick and then you’re just stuck in this job and you weren’t sure you wanted it. So that’s one mindset shift is really thinking about the motivation and the why.
Pete Mockaitis
If I may pause right there, and say that is so valuable to not just fall for the trap of, “Oh, it’s the next step.” I’ve lived it myself. I remember, in a volunteer organization, one time I was the seminar chairperson, which was fun. I’m in charge of this whole event. And I’ve got my team and volunteers and all the thing.
And so, I’ve been volunteering for a long, time and I say, “Oh, the corporate board president for the state is the next role, so, naturally, of course, I should do that.” But I was just a fool. I didn’t stop and think, “What is this role about? Oh, this is about, like, compliancy things and like running a board, and making sure we have the audits done, and the bank account in good shape, and things are filed with the right entities, ensuring that we are in good standing with the mothership, the parent organization.”
It’s like, “Oh, I hate all of those things.” Like, I love being in the mix, and running it and, and doing the creative things. And then that wasn’t there. And I’m reminded of Star Trek. Jean-Luc Picard got some advice from an Admiral at Starfleet, saying, “Don’t ever let them take you out of that chair because this job, it’s more senior, but it’s not nearly as cool.” And so, having a good picture, eyes wide open in advance, can save everybody a lot of heartache.
Carolyn Dewar
Absolutely. I sit here in Silicon Valley, and so tons of tech friends and tech people around me. You can get someone who’s amazing at technology and, somehow, we’ve decided the way to reward them is to promote them into a people-leader role where they’re no longer doing the tech and they’re just managing.
A lot of them, they hate it. They’re not good at it. And it’s not the highest and best use of that person’s talent, right? So how do we really make sure you even understand what’s involved in that next role and have an honest conversation with yourself on, “Is that a great fit?”
Pete Mockaitis
Beautiful. Well, let’s hear about the next season, summer.
Carolyn Dewar
So, the next season is, you’re now spring, you’ve sprung out as a little bud, you’re in flower, you know, it is summer, you’re in the role. And a lot of folks think about, “Okay, I’ve got the job now. Now what?” And a couple of ways to think about that first time, absolutely important to spend time listening and learning.
Frankly, people are going to tell you stuff when you’re new, honest things, hard things that they may not tell you a little bit later on in your tenure. So, when you’re doing that listening tour, you’re getting around talking to employees and customers and regulators, whoever it is, ask the hard questions.
One of the CEOs talked about, when he initially went out, he said, “Well, what’s the thing that you were all afraid to tell my predecessor? What is it that I need to know that they didn’t know?” It’s such a great question.
And because you’re new, they know you’re not fully associated with the track record so far, and so they’re willing to be honest, “What’s working? What’s not working? What are some of those elephants in the room that no one’s pointing out, but we really need to address?” And so, really use that time to soak up and learn.
I say it’s not enough, though, just to listen. You actually do need to start acting and hit the ground running. And we talked about nailing your firsts. Your first top team meeting, your first town hall, your first board meeting, your first quarterly earnings. You really do only have one chance to make a first impression.
And so, how do you go into those moments being really conscious of, “What’s the tone you want to set? How do you want to show up as a leader? What signals do you want to set in terms of your expectations and where you’re going to take the place?” And so really being mindful because, whatever you do in those moments, will have a ripple effect down through the organization, whether you were intentional about it or not. So, you want to set the right tone.
Pete Mockaitis
Oh, that is powerful. And I love that question. And, boy, it really speaks to a reality that we, people are quite reluctant to criticize folks who are more senior than them or even, tangentially, criticize them in terms of like, “This thing isn’t working and you are kind of the person in charge, so it’s, in a way, kind of your fault.” So, yes, seize that window and a fantastic question, “What were you afraid to tell my predecessor?”
And I also want to get your perspective, when getting, nailing these first and having big wins. It’s funny, because, of course, your predecessor was also, hopefully, you know, trying hard to win a lot and nail things well, and you’re new and have less experience, so that kind of seems like a tall order. Do you have any pro tips on, is there any way we can identify some easy quick wins or any little tips and tricks and hacks to be able to pull that off?
Carolyn Dewar
I think my brain is going in two places. One is the practical, and we can get into how you identify what you’re going to do to lend value and what the strategy should be. That’s one thing. But the hacks and tips, it’s a bit of a delicate time, especially sometimes your predecessor is still around. They might’ve gotten promoted too and they’re your new boss. Or, even for CEOs retiring, I think 17% of them now stay on as executive chair and they’re still coming to work and they’re still involved.
And so, how do you both set a new tone without completely throwing them under the bus in a way that’s unproductive? And I’ve seen folks do this judo move a few different ways. One is, it’s usually true, the context has changed. So how do you celebrate the past and say, “Here’s how we got here, here’s what’s great, here’s all the things that we all should feel proud of”? Because people want to feel like you see them, especially if you’re coming in from the outside. You get with how they got there.
“But, look, here’s what’s changing. Here’s what’s going on in the external world. Here’s what’s going on with our aspirations that’s changing and implies that we might need to do something differently. What got us here might not get us there.” That’s sort of an elegant way that I’ve seen a lot of leaders nuanced that, especially when they want to be really respectful to the past.
I think it’s different when you’re stepping into a complete turnaround and everyone knows there’s burning ships and you’ve got to just wreck and rebuild everything. I think, in a way, it’s easier to drive change in those moments. You don’t have to be quite so nuanced. I think, when things are going reasonably well and you just want to continue and make it better, that’s where you’ve got to be a little bit more thoughtful in how you communicate.
Pete Mockaitis
Okay. Thank you. Okay, well, let’s hear about fall.
Carolyn Dewar
Sure, let’s go into fall, and this hits on your question a little bit, too, about how you know big moves. The big risk in the fall, this is your middle years. You’ve gotten out of the gates, you’ve done well, the initial strategy, the initial team have delivered, and now you’re trying to think about what to do for years three through 20, however long those are going to be.
The biggest risk is your own success makes you complacent. Things have been going well, and so you hope you can just keep running that play and it’s going to continue to go great. That’s when leaders feel caught out. I know Jamie Dimon at JP Morgan talked about that was his biggest risk. And even when the “London Whale” happened and things that he dealt with, he said, “I got a little complacent. I assumed the things that have been working would just keep continuing.”
So, how do you break through that? I think about Michael Dell, the Founder and CEO of Dell computers. He’s been a CEO since he was 19. So now it’s been, gosh, I think half a century, if you think about it, or almost, that he’s been a CEO. He’s had a few of these times where he’s had to say, “How do we refresh? How do we not sit back on our laurels?”
And one time, he went into his leadership team, and he said, “Imagine it’s three years from now, and there’s a new player, a new attacker that understand our customers, understand our business. They’re better than us. They have new products. People love them. They’re really threatening our business. Now let’s assume that that attacker was us. What would have to be true? What was it that we were doing that we could disrupt ourselves and be the greatest threat to our current business? What would we look at?”
And it forced them to take a real outsider view, to look at it from the outside, and say, “Where are the opportunities? Where are we getting lazy? What could be possible given what’s happening in the world?” and they kind of reinvented themselves. You see companies do that reinvention several times. Lego has done the same, right? Who would have thought they would have ended up in theme parks and movies and adult Lego and all these other things?
It’s because they stepped back, and said, “I don’t want to just be a little plastic bricks company that, hopefully, you don’t step on in the middle of the night.” And so, how do you ask those questions of your team, ask the questions of yourself and really provoke yourself to not get too comfortable?
Pete Mockaitis
And to this point, I also want to hear, how do we become the rare, less than 1%, or 0% right now, CEO or a leader who is truly getting the full scoop from their team, from their direct reports, and able to have an honest assessment of their relative strengths and weaknesses?
Carolyn Dewar
Yes, so important, right? And I think you have to be really, really deliberate about it because, as soon as you’re made CEO, your jokes are funnier, you’re taller, all these things happen, and people start treating you differently. I think the CEOs we talked to put very deliberate things in place. Most of them had kind of a kitchen cabinet or an unofficial mini board that they went to for advice. It might just be three, four people.
Maybe someone in the organization, often people outside, maybe it’s other peer CEOs, maybe it’s other advisors they have, but they’ve got a small group of people who will hold up the mirror and tell them the truth about how things are going. That’s kind of one technique that we’ve seen. I think there was one CEO who had a reverse mentor.
So, they picked someone two, three levels down in the organization, someone who normally wouldn’t have direct access to the CEO. And they built a relationship with that person over time and gave them permission. In fact, really asked them to teach them, “How are things landing two, three levels down in the organization? What’s the chatter that I need to know about? What’s the feedback for me?”
But also, it turns out, that person, in this case, were younger, they were more tech savvy, they were kind of further ahead on some of the changes that were happening in the industry, and they learned a lot. And it became this kind of reverse mentoring relationship, which was very, very cool.
One more final just tactical one is, even in your meetings, you can use things like devil’s advocate, for example. If everyone is getting excited about an idea, especially if they think the CEO wants the idea, the risk is people fall in line and they all just start agreeing. Can you appoint someone in the meeting explicitly to say, “For the next five minutes, we want you to critique our idea and tell us all the reasons why it’s terrible and what aren’t we thinking of.”
It gives permission to someone to play that role and they can be purposely edgy and no one can be mad at them because they’re like, “Well, I was just playing the role you asked,” right? That’s a simple technique, but any of us can use that to make sure we’re really getting into it.
Pete Mockaitis
Yeah, that’s excellent because, I think, a lot of folks really need perhaps dramatic intervention to contradict those instincts of, “Be agreeable and do what the person in charge seems to want.” And so, I think that’s a very clear and direct way to achieve just that.
Carolyn Dewar
Yeah, absolutely. You have to create a safe space for people to do it. And they recognize pretty quickly, if you react badly to the honest feedback, you’re not going to get it again.
Pete Mockaitis
Yep, certainly. Okay. And winter?
Carolyn Dewar
So, winter, by design, and it is a cycle because it does overlap very much with spring. As you’re preparing to hand over the reins and to finish strong, that’s the same time where that new candidate is getting ready to take on the role, so you need to think about them together. I think it’s a phase that is really under, people don’t talk about it enough. There’s a lot about first hundred days. There’s almost nothing about last hundred days or last year, and what does that look like.
I think there’s a few things going on. One is there is a very personal journey, that outgoing leader, especially when it’s planned and it’s a retirement, is going through. It’s been a huge part of their identity, usually for years. And they have to get comfortable with it’s time for them to go. So, they actually set timing and talk to the board about when it’s time to go. Are they excited about what’s next for them, whether it’s, you know, friends and family or boards or whatever it is they’re going to do?
They need something they’re excited to go to or else sometimes you see people hanging on too long, to be honest, and that’s not good for anyone, especially if they’re hanging on because they’re worried about not being relevant or what’s next. And the best CEOs have this conversation all the way along. So again, Brad Smith of Intuit talks about he had this conversation 44 times with his board, which meant every quarter for the 11 years of his tenure.
Right from the very beginning, he started with, “How am going to prepare my successors? How are we going to start putting people in place to be a great bench of leaders going forward?” Because sometimes it feels awkward if you wait till the end. Who’s going to be the first one to say, “Hey, maybe it’s time to move on, right?”
But if you’ve had the conversation all the way along, you’ve built a great bench of leaders, then your focus can be on the right things, which is how to hand over with grace. Is there some cleanup you’re going to do to make it easy for the next person? Maybe there’s some lingering talent discussions that have to happen that are overdue or some budget issues.
Clean that up. Use your political capital to get some of the hard stuff done so that the new person taking over can do really, really well. I think we’ve seen a few of these boomerang CEOs in the last while, where they leave and then the new person doesn’t work out and they have to come back. I don’t think that’s a great sign of your legacy. Part of your legacy is that the organization continues strength to strength after you. You shouldn’t want to have to boomerang back.
Pete Mockaitis
Well said. Well, so walking through all this, I’d love it if you could share with us any story of a CEO that’s really stuck with you in terms of it’s made an imprint in terms of a lesson or a way to play the game a bit differently that made you go, “Yes, that is excellent.”
Carolyn Dewar
I think it comes back to where we started, which is the learning mindset of these excellent CEOs. And not only is there just a natural curiosity and humility, but they built it into their calendar. They made time for it, right? So, Satya Nadella spends one day a month doing nothing but learning. Now he’s Satya, so he can, like, cast the net wide and he has the world experts on everything submit things for him to spend and read during that time.
But the number of CEOs who really had something deliberate about how they would learn, they show up in their peers, they attend different sessions. Again, Brad Smith at Intuit used to do job shadows with other CEOs. All the way in, it’s like a 10-year, he would go and like shadow, you know, the Ford CEO or, he would shadow Zuckerberg at Facebook and learn from him. I mean, this is someone already a decade into an amazing career.
I think their willingness to admit they have something to learn and then making the time for it is role-modeling for all of us, as well as it makes them better CEOs. So that’s one that really stood out for me.
Pete Mockaitis
Well, that’s beautiful. And, yeah, I’m reminded of Bill Gates as well. He has the “Think Weeks” just disappears with the books and Diet Cokes, and that’s what he’s doing. It’s like, “Okay.”
Carolyn Dewar
And goes off to a cabin somewhere? Yeah, absolutely, right?
Pete Mockaitis
Super.
Carolyn Dewar
And we can all do that even in micro ways, right? Maybe you can’t take a whole week, but it’s not selfish or self-indulgent to invest in time for you to learn because it’s going to make you better at your job. And so, how do we not treat it as just sort of a nice-to-have that always gets punted off the calendar?
Pete Mockaitis
Okay. Well, Carolyn, tell me, any final things you want to make sure to mention before we hear about some of your favorite things?
Carolyn Dewar
I think these were the biggies, other than these amazing CEOs, it’s easy to be sort of wowed by them, but 90% of what we learned and what we talk about in the A CEO for All Seasons applies to any leader. These are phases we all go through. We’re getting ready, we’re new, we’re kind of in role, we’re thinking about what’s next.
And so, I think there’s learnings for everyone. There are also learnings for anyone who’s supporting a CEO. It’s good to understand their journey so that you can work with them well and support them over time. So, investors, boards, others have also looked at this, and said, “Oh, wow, it’s worth being really thoughtful about what happens at each stage.”
Pete Mockaitis
Okay. Well, now could you share a favorite quote, something you find inspiring?
Carolyn Dewar
It’s probably a quote and a tip that we heard. So, this was Michael from Cincinnati Children’s Hospital. He talks about your to-be list. And he doesn’t just talk about it, he does it. So, as well as your to-do list with your agenda every day, he writes next to each meeting, “Who does he need to be in that meeting?” which is interesting, right? It’s not just about being inauthentic or not being himself.
But he’s recognizing like, “What does the organization need of me as its leader in that moment? Do they need me to be decisive and just stop the swirl? Maybe in this town hall, even if I’m having a crazy crummy day, I need to be inspiring. I need to show up that way.” So, this whole idea of how you show up and how you are is just as important as what you do. Really, I always come back to that thought.
Pete Mockaitis
All right. And a favorite study or experiment or bit of research?
Carolyn Dewar
There’s an old experiment called the lottery ticket, which is about, recently, they’ve done it thousands of times. A room full of people. You give half the room a number with their lottery ticket on it, and half the room a blank piece of paper, and you say, “Write your own number between one and X. That’s going to be your lottery ticket number.”
Just before they’re pulling the winning ticket at the front of the room, they call time out, and they go back out on the floor. And then the question they’re trying to answer is, “How much more of anything do we have to pay the people who wrote their own number versus those who were given a number?” So, quick picks versus filling out your own lottery number. How much more do you think you have to pay the people who wrote their own number, if at all?
Pete Mockaitis
You mean, to take their ticket from them?
Carolyn Dewar
To buy it back, oh, sorry. To buy it back. Apologies. So, you’re offering to buy back the ticket. How much more do you have?
Pete Mockaitis
Oh, this is juicy. This is fun. Well, it’s like, I’m thinking about the IKEA effect in terms of they put effort into it, or these numbers are special to them, so it’s more than zero, but I’m guessing it’s irrationally high if you love it so much. So, I don’t know, 20% premium?
Carolyn Dewar
That’s a good guess. It turns out it’s five times more, which is completely irrational, right? It’s completely irrational. I think what it means for leaders is, if you can involve people, if they feel part of shaping it, if they feel like they’ve had their fingerprints on your strategy, your planning, whatever it is you’re doing, their level of buy-in and commitment is irrationally high.
And that’s a great superpower for you to tap into as a leader. And so, just telling someone the right answer versus bringing them along, it might be faster in the short term, but it doesn’t get you as far.
Pete Mockaitis
Beautiful. Thank you. And a favorite book?
Carolyn Dewar
I like ones about people and dynamics. So, it’s older now, but the Born a Crime by Trevor Noah, it’s just a fascinating one. It puts you in a different mindset of, “Gosh, we can’t all assume that the way we grew up is the way everyone does.”
Pete Mockaitis
Yeah. And a favorite tool, something that helps you be awesome at your job?
Carolyn Dewar
I am starting to play around with AI. I think I’m very much a newbie. I saw Sam Altman was talking about how Boomers use it versus how Gen X and Gen Z use it. I’m probably somewhere in the middle. I’ve moved beyond using it as Google, but I’m just starting to play around with little ways to build it into my day.
Pete Mockaitis
And is there a key nugget that you share, in your writings or with your colleagues, that people really dig and they quote back often to you, a Carolyn original?
Carolyn Dewar
I think the to-be list one that I shared is a big one. I think the only other one is this idea of doing what only you can do and how freeing that can be. And so, if you really think about the hours you have in the day and what’s the highest and best use of that time, and you lived your life that way, it’s freeing for you, it’s higher impact for others, and I think we’d all be better served if we kind of operated in that mode.
Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?
Carolyn Dewar
Sure, you can always find us. I think if you type in A CEO for All Seasons and McKinsey, it’s going to get you to our homepage, and there’s access to any of our authors and video clips and things to read. So that’s probably your best bet.
Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?
Carolyn Dewar
So final call to action is probably this idea that, ultimately, it’s not about you. You’re being given the privilege of being in this role, and your goal is to leave it better than you found it and to do everything you can to sort of serve all your stakeholders while you’re in the role. And I think that prompts all of us to think bigger and bolder about what we’re trying to do, and also get out of our own way a little bit.
Pete Mockaitis
All right. Carolyn, thank you.
Carolyn Dewar
Super. It’s terrific to talk to you. Thanks so much.






