What the Best Leaders Know — and What Skills They Develop

Deals not just another payroll platform, it's when your team might actually enjoy. HR, IT, and payroll together finally, built in-house, built for peace of mind. Visit D-E-E-L dot com slash HBR podcast. Welcome to the HBR IDA cast from Harvard Business Review. I'm Kurt Nickish. There's a memorable interview with the CEO that I read in the New York Times years ago. It was with Duke Energy's James E. Rogers. In it, he talked about how his reports would delegate up. With email, he said, "It's just so easy to pass decisions along to him." And he would sometimes simply respond, "Your call." I remember that more than a decade later. There's a lot of leadership maturity in being able to say to your team, "Your call." To allow them to make decisions for the organization and to live with them. That is just one of many insights that Adam Bryant has won from interviews over the years. He wrote the Corner Office interview series for the Times and has interviewed hundreds more people for his new book, The Leap to Leader, How Ambitious Managers Make the Jump to Leadership. He says that the most underappreciated aspect of becoming a senior leader is that it demands a new way of thinking, a mindset shift with a careful plan around that. Here to tell us more is Adam Bryant. He's a senior managing director of the ExCo Group. Adam, thanks for coming on the show. Thanks for having me, Kurt. Adam, why is the transition to leadership so rocky for so many people? It's just such a significant step. And I think to me the biggest difference between a manager and a leader is a manager. Usually somebody is handing them kind of expected outcomes. It's like this is what we want from you and your team. We're giving you resources. Please fulfill this playbook that we are handing you. And to me, to be a leader is to write the playbook. And yes, maybe there are things that are expected of you and your team. But to always be looking for opportunities. What is the problem that needs to be solved that maybe the boss isn't seeing or that the company isn't seeing? To take the company where it needs to go, to tackle the tough problems, to do that with courage, to be able to place bets and be wrong, and maybe even risk your job. But to me, that's one of the big mindset shifts to become a leader. Gotcha. So this is way more than just, you know, here are these great skill sets I've developed. And now I've been promoted. What does an unsuccessful transition to senior leadership look like? You know, where do people go wrong with this? Boy, how much time have we got hurt? I mean, look, leadership is so hard, right? And I honestly think it's one of the hardest things on the planet. That's why for me, it's so endlessly fascinating. And there are so many traps that people can fall into in this age of so much disruption and uncertainty. If people are looking for certainty, if they want to create a strategy document and put it on a spreadsheet and take it out for the next three or five years and then get frustrated when the world doesn't comply or employees don't comply with that. It's just a recipe for disaster. If you go in with these jobs thinking it's like, okay, I'm going to have a certain amount of control. You're just going to be disappointed and frustrated and ultimately become a bad leader. Everything to me about leadership is this kind of balancing act that sort of handling a series of contradictions or paradoxes. And yes, you have to have it kind of a clear and simple plan about the direction that you want the company, the team to go. But also create enough room for adaptability and flexibility. And if the world serves up some different data or information, you say to your people, okay, we're going to flex. And so there's so many paradoxes and contradictions of leadership that require you to be in that sort of center point and know which way to flex depending on the moment. And one of the biggest ones we've been living through just these last few years is this notion of compassion. I mean, people are dealing with a lot during the pandemic at home. And everybody's being told you got to be compassionate, but you also have to hold people accountable. And you have to create a sense of urgency, but also be patient. You need to be inclusive and give, make sure everybody has a sense of belonging. Yet you also have to be clear about what your values are as a leader and what you stand for as a company. And so there's just all these new challenges around leadership that, for me, I pick a number card. I mean, I think leadership has gotten five to ten times harder just in the last few years. It's a big shift already for somebody to move from being an individual contributor to a first-time manager. Is this shift to a senior leader, a bigger shift? As you move up, I mean, I think what changes is that the problems that land on your desk become harder and harder. There's more gray areas, you know, all the easier decisions are taken care of below you. And so you just got to be comfortable making decisions with less and less data. And have the thick skin to know that whatever you decide, it may anger or annoy some constituent. But to have the courage of your convictions that what you are choosing and deciding is ultimately best for the organization. Another one is that as you move up, I like the expression that leaders are over red. And so you need to be so aware that you are being studied at every single moment. Like, people are watching, like, just are you fering your brow? Are you hunching your shoulders a bit? Are you a little concerned? Do you seem distracted? People can take those tiny little signals and create really dark narratives out of those things. Like, oh no, the company is being sold or we're going out of business. And so you have to have that level of self awareness. Another hallmark of this era of leadership we're in right now is that people expect, you know, all these words about humanity and transparency and compassion and authenticity. This is what leaders are hearing. This is what people want. And those are big words. And we can spend a lot of time unpacking what they mean. But I think one of the demands it creates is that four leaders, they have to be much clear about who they are as a leader and what their personal values are. And the way I often describe this is that when people are moving up in their careers, you know, we're all taught, we've got to have an elevator pitch, right? But I don't think people spend enough time thinking about what their elevator pitch is for who they are as a leader. And you may go through your entire career as a leader and nobody will ever ask you who are you as a leader. But I think if you spend some time on the introspection, reflection, where you become really clear about like these are say the three values that matter to me most. And it's not just words, it's not just fridge magnet poetry of leadership. You've got to be able to answer the double click questions that people might ask. It's like, okay, you say those are your three most important values. But why are they important to you? How did they become important to you? What do those look like in action? You know, how do you make sure you hold on to those when you're under stress? You've worked with lots of people who are making the move to senior leadership. Are there other aptitudes or mindsets that you look for to see if somebody's, you know, ready, ready for that move? Yeah, one of them in this sounds really simple, but just having the clarity about why you want to lead because I think a lot of people when they're looking at jobs and plotting out their career, there's this sort of built in assumptions like I want that job and leadership jobs are really tough managing people is really tough. I think people need to spend some time reflecting on why they want those jobs, right? Because expression I heard from one CEO, like everybody wants the CEO's job until they have the CEO's job, right? And I think it's true for a lot of these big jobs. I mean, you know, the hours are long, the problems become more difficult. You're dealing with more people and all their challenges. And so just being clear to yourself about why you want to do it. And I think that if the answers are for power and money, those aren't good answers because the day is past when you can, you know, wield power as a leader just doesn't work and cultures anymore. And whatever you're paid, you know, the sacrifices are just so steep in these very senior jobs that the money is ultimately not going to feel worth it. So you have to first of all be very clear about why you want to do this. I interviewed a young CEO years ago for corner office woman named Layla John, who unfortunately passed away when in 2020 from cancer. But, you know, I had this fascinating interview with her. She was telling me about her childhood and Kurt was this horrible childhood. I mean, she's removed a ton. She was bullied at every school. She went to so many problems with her family and her parents and things like that. And when I was interviewing, she had such an incredibly positive attitude. And at one point I asked her, I said, where did you get your positive attitude from? And she said, just a handful of words that I have never forgotten. And she said reality is just source material. And it was such a powerful insight for me because we've heard the expressions, we all are the stories, we tell ourselves, but if you think of reality, a source material, it creates an ability to sort of step outside yourself and help you analyze, like, why are you thinking that way? And I just think if you have this ability to understand that personally, that you have the power to create and influence the narratives you are telling yourselves, I think that insight, and if you can practice it with yourself, I think it's an incredibly important and crucial skill as a leader because what you are doing as a leader in many ways is creating narratives for your team for the organization. I mean, strategy is just a part of the narrative. Another part of the narrative is the mission, the purpose, the values, the culture, you know, the general direction you're going, why you exist, it is your job to create those narratives. Is ambition important here? You know, there are people who don't really seek leadership, but it comes to them. Yeah, and, you know, I feel like we could talk for hours just about that one word ambition, especially as we've been in this kind of quiet quitting year for a while now. It is why in the subtitle of book, how ambitious managers make the jump to leadership. I wanted that word to be in there because I wanted to acknowledge that, like, if you're not ambitious for these jobs, there's no judgment there, right? Like there's no assumption that if you're a really great individual contributor that you should want to move into these leadership positions and I think companies fall into a trap where they assume that people want to move into these top roles and they don't necessarily do. You need to be clear about what ambitious means and if you do self-identify, if you do say to yourself, I am ambitious, then I do think you should double and triple click on that and say, well, why are you ambitious and what are you ambitious for? What are you trying to achieve? What does winning look like for you? Very often that if the leadership positions are the goal themselves, or is it just a platform for you to have a greater impact for you to achieve the things that you want? So again, we've been talking about sort of self-awareness and reflection and to me, this is part of that. You have so many great little takeaways in this book from all these interviews with CEOs. Can we do a little bit of a lightning round where I run through a few of the takeaways? Please. Beware the logic box. Yes, this is something that I learned personally the hard ways. So the logic box is my shorthand for how you can find yourself, start fooling yourself into thinking that you're making really smart choices and smart decisions. But if you raise yourself out of to a higher altitude, you realize like you're making smart trade-offs and choices among the choices that you see in front of you, but you're basically in the wrong box. The whole framework is wrong and you shouldn't be in it anyway and I sort of realized this myself. I had a couple of things like some real estate deals that I almost did and there was a book proposal that I was so certain was 100% right and then I realized like ultimately is like, what was I thinking? I had so many moments where I was saying myself, what was I thinking? And so I developed this metaphor of like, you know, you're trapped in a logic box, you're making really smart choices and decisions from a bad set of options. So it's just something as a leader, I think it's a handy thing because you always have to be super clear on what problem you're solving. Companies can get trapped where they're like solving for the wrong thing. So it's just like, it's a good check, you just sort of say to yourself, you say to your team, are we trapped in a logic box here? Look in the ugly mirror. Yeah, it's what if you're takeaways. So a challenge for a lot of companies and leaders is that they want to be cheerleaders for how awesome the company is and this can happen to teams, but you just like, you know, you want to be a positive leader right? You want to set tone and keep everybody motivated. And so everything is like great. And there's a little bit of a cheerleader trap that people can fall into. And I think it's essential for every leader to be brutally honest with yourself and with your team at large about what are the challenges you face? What is the brutal honest reality of the context that you're facing? And as much as you want to say, like you're killing the competition, if you're not, you got to be brutally honest about it. Because to me, that's the first step in ultimately driving transformation because you have to be able to say to people, look, we need to change what we do. Status quo is not an option. We need to get better. And the starting point is to be able to say, this is why we are not good enough, right? This is, this is the ugly mirror of the challenges we are facing and we need to be brutally honest with ourselves about that if we are going to change and get to a better place. You also recommend mastering the art of compartmentalization. What does that entail? I have met a lot of leaders over the years. You have two. We all work for a lot of different bosses. And I think you can plot them kind of an on to continue more in x, y, axis, if you will. There are some people who have like a tremendous amount of empathy and they feel the weight of the impact of their decisions. And you can over index on that, right? The empathy is good, but you can have too much of it. And it can get in your way as a leader because you sort of feel the mood of the room and individual employees and you feel the weight of every single decision and imagine all the consequences of it. And you can find yourself staring at the ceiling for three hours every night when you should be sleeping. On the other extreme, we've all met leaders who have seemingly no empathy at all, right? And at some level, it's good in the sense that they may not be picking up on the body language and signals and the impact. You know, you need some of that to be a leader because everything needs to be filtered through like what is best for the organization and, you know, CEOs at some point in their tenure, they might have to upgrade their their leadership team. So people, they worked with, they hired personally, they need to sit down and say like, I know you and I spent a lot of time in the fox hole together, but you're not going to get us where we're going to need to go. It is that balancing point of like you need to have the empathy so you could pick up the signals and just have good antenna in general for people and, you know, culture and things like that. On the other hand, you've got to be able to sort of make the hard decisions and live with them and not chew yourself up because then you're not going to be effective. I often think about something that former CEO named Bob Brennan told me where he works a lot with young entrepreneurs and he sometimes tells them if they're beating themselves up, he says, you know, if you talk to your friends the way you talk to yourself, you wouldn't have any friends. Set the bar for your team's performance. What do you mean by the setting the bar part? If the leader is the one who's decide like, okay, this is what great looks like this is what good looks like and this is what middling looks like you're essentially setting expectations for the team. And as a leader, I mean, the traps you can fall into, you can make it so ambitious that it ultimately becomes entertaining and people go, well, you know, we're never going to get there. So it actually destroys morale. You can set the bar too low where people succeed just by getting up in the morning and running a comb through their hair and that's not good enough. So to me, it is one of these, it's kind of like an infinite learning curve as a leader and I've talked to so many leaders about this and they make the point that you never, you never get it exactly right like every day. You sort of fiddling with the knobs or as one CEO described it, it's like a sound mixing board right like just making these constant adjustments for what does good look like and that that important insight that you are setting expectations, you are setting the scoreboard and to understand the impact of that. Another takeaway that was common across the folks you talk to is know your triggers and this goes in the bucket of self awareness, right. And just being really clear with yourself about those things that kind of set you off and that prompt these outsized reactions that may not be completely rational and especially when everybody's watching. Exactly. We're all human beings, we've all got our quirks, we've all got our triggers. It might be something based on when we're kid growing up, but you have to be able to step outside yourself and know what those are. You need to have a plan for managing them and how you keep yourself in check because it's again CEOs are over red, they're every, you know, furrow of your brow, every word you have to imagine you've got like 10 megaphones on your shoulder that is amplifying those. And when you have these sort of outsized reactions, they're they're going to become just part of like company legend of like, you know, somebody punched a hole in the wall after a meeting or something and you might have something like that over 10 years, but people will be talking about it for a long time. I often think of this expression that Ron Williams, a former CEO of Etna Shared, he said, leaders need to he called it trade in a narrow range. It basically means like your your mood, your behavior shouldn't go from extreme to extreme. Right, you need to be predictable and I think predictable has like downsides to it, but I think it is really important to be predictable as a leader because if you are unpredictable. Then people are going to be spending a lot of their energy trying to figure out what mood you're in today when they should be thinking about the work. Consistency, right? That's what predictability gets to there. That was another takeaway in the book, provide context. There was a Chevron executive, biology, Christiana, mercy, he shared with me and it really stayed with me and his basic point was that just about everybody thinks they are making the right decision, whatever their role is in the company, everybody thinks they're making the right decision based on the context that they have. And that context may be very narrowly defined and they think within that context, me doing this is the best for the company, even though it may be serving themselves or advancing their particular part of the business. And so what biology was saying that you have to create that broader context for people so that everybody has the shared context of what the company is trying to accomplish within the broader industry and all the challenges it's facing. And by relentlessly communicating that context, you are much more likely to get people to make the right decision to help drive the strategy and it comes back to this idea of narrative and alignment. But your job is leaders to create that shared context, a shared story, a shared understanding so that when people say themselves, well, should I go left or right, should I choose chocolate or vanilla, that they have the broader context that helps guide them to what is the right decision. One thing you recommend is that people really hone their decision making and they do this even before they become leaders, that they practice it and work on it. Look at successful, really successful executives, what do they do differently in their decision making that makes them stand out? It starts with acknowledging that whatever problem you're facing or decision you have to make at a very senior level is probably a tough decision. Part of the becoming a leader is recognizing that you don't really have too many easy days anymore, right. So you're probably staring at a really tough problem for which there is no obvious answer and there's negative consequences, whatever you choose. So the first thing is to get comfortable with that reality. Secondly is be able to make a call. I've talked to a lot of CEOs and sometimes I ask them like when you're taking on a new role at a new company, you have to decide with the existing leadership team who's going to stay and who's going to go. And what is your framework from that and what I've heard over the years, a lot of them say I need people who can make decisions because a lot of people are afraid to or they just really struggle with making a decision because making a decision involves risk, right. You're choosing left versus right and putting yourself at risk and a lot of people just have problems doing that. So realize that part of your job is to have the courage to make the decision and to own it. And then I think as much as you can get as much input before you make the decision and don't feel like you have to make the decision alone. I mean one of the most courageous and powerful things you can do as a leader is to say I need help and what do you think and making sure you get as much as many different perspectives and insights from people on your team before you make a decision. That's one of the many benefits of diversity, right. You have people who see the world through different lenses and might spot something that you're not seeing. So to me, those are just few of the key strategies for making good decisions and actually making the decision in the first place. So there are a lot of small insights that people can use and apply. There are a lot of big composite lessons here. I wonder what piece of advice you would give to somebody right now who's earlier in their career. Maybe they're still an individual contributor or a young manager. What if they're at that stage in their career, but they have the ambition to go a lot further. They have the benefit of time, right, that they're going to be able to work on these things. What should they do today? What's a big focus for them going forward? To me, it's about being clear about why understanding your motivations that if that person you describe is saying, you know, I think I would like to move up into these leadership roles to spend a lot of time, reflection, internal work, being clear about why you want to do it. I also think they should spend as much time as they can talking to senior leaders so that they really understand what the job entails, right, so that they go into these roles, clear-eyed and they know what they're signing up for. Because I think there are just too many people who just say, "Yeah, I want that job. I want that promotion." And then they get the promotion and then they realize that most of their days spend dealing with people's problems and putting out fires and all these challenges. Maybe the thing that they really love doing, you know, the thing that is their superpower that really motivated them is actually now a much smaller part of their job and they really miss it. To me, that would be my advice to them. It's like, be clear about why you want to do it and do as much work as you can to find out what job you are signing up for so that gap between the theory of the job and the reality of the job is very small. Because I think for a lot of people that gap can sometimes be big where I thought I was signing up for this, but now the job is that and I kind of wish I knew that, but you need to take some control and ownership for the fact that you should do some detective work before you commit to a big new chapter of your career. Adam, thanks so much for coming on the show to talk about this. Really appreciate the time, Kurt. Thank you. That's Adam Bryant. He is a Senior Managing Director of the Exco Group and he wrote the new book The Leap to Leader, how ambitious managers make the jump to leadership. And we have more episodes and more podcasts to help you manage your team, your organization and your career. Find them at hbr.org/podcasts or search hbr, an Apple podcast, Spotify or wherever you listen. This episode was produced by Mary Do. We get technical help from Rob Ackart. Our audio product manager is Ian Fox and Hannah Bates is our audio production assistant. Thanks for listening to the hbr.id cast. We'll be back with a new episode on Tuesday. I'm Kurt Nickish.