234 | Adam Bryant – The Leap To Leadership 26-Sept-2023

0:00And now, Taking Care of Business, your hosts, Craig Moen and Shai Gillad. Welcome to Business Owners Radio, episode 234. Our guest today is Adam Bryant, author of the new book, The Leap to Leader, How Ambitious Managers Make the Jump to Leadership. As the creator and former author of the iconic corner office column in the New York Times, he has mastered the art of distilling real-world lessons from hundreds of interviews and turning them into practical tools, presentations, and exercises to help companies deepen their leadership benches and strengthen their teams. Good morning, Adam. Welcome to Business Owners Radio.

0:46Great to be here. Thanks for the invitation, guys. Yeah, we're so excited to talk to you today about the new book, The Leap to Leader, How Ambitious Managers Make the Jump to Leadership. Tell us what inspired you to write the book. Sure. And a bit of context might help. So over the last 12 years, I've interviewed more than a thousand CEOs and mostly CEOs and other senior leaders with a very specific focus about key leadership lessons and how they think about leadership. And all those interviews I've done, I've never asked any of them a single question about their companies or their strategy or broader macroeconomic forces.

1:22It's all about leadership. and you do thousand interviews or more and you start seeing patterns and good questions emerge and i've written four books now um and my most recent the leap to leader with all my books there's a an underlying question that i find really interesting and i don't quite know the answer to and that's sort of why i i write books to help me answer the question so the underlying question for The Leap to Leader is really focused on sort of more the internal game, the mindset shift that you need to make to be a leader. And when I think about leadership, I think of in two sort of big parts.

2:02One is sort of the external game of leadership, right? Setting strategy, working with your team, all the things that you're doing, customers, all those things. And just as important is the internal work that you have to do to be a leader. And that's what this book really gets into. What does it mean to be a leader? Not about what's on your business card, your title, and you might be managing five people or just started a company with 10 employees, but you are a leader and you can lead. That's what I really wanted to explore. The timing has worked out pretty well because I think that leadership has gotten, pick a number, five to 10 times harder just in the last few years.

2:42And so I feel like it's a good moment to sort of step back and say, what does it mean to lead? And how do we sort of own all these challenges and disruptions and uncertainties that we're facing now? Yeah, it's interesting, you know, talking about sort of the strategies and the structure around leadership, company facing things like you mentioned, but this trickier part of how you walk the walk. And I think with all the disruption we've seen in recent years and the disruption surely to come, I don't think that those two things are discrete anymore. You know, there is no discrete internal messaging, for instance, right?

3:20Your internal messaging is your external messaging because it all gets out there eventually, right? And the call to transparency. So how are leaders thinking about that challenge now? Well, you mentioned sort of the blurring lines between the sort of the personal and professional, the broader society, and everything is sort of bleeding into everything else. And I think that means for leaders, we're hearing a lot of more words that are important for leadership just in the last few years. And you guys have heard them like humanity, vulnerability, authenticity, humility, like all these things that people want and expect from their leaders.

3:59We can spend a lot of time talking about, like, those are big ideas and big words. But what I think it means for leaders is just that as they're navigating the internal challenges, the external challenges, figuring out, like, what is the role of companies in society? Wendy weigh in on issues more broadly, is that you have to do a lot of internal sort of excavation work and reflection about who you are as a leader to figure out what your personal values are and why they're important to you and how they became important to you and what those look like in practice. And I like to use metaphors. And I think if you do that work and figure out who you are as a leader, that provides a little bit of like a center board on a sailboat.

4:45And the point of a center board on a sailboat is to keep you in a true direction, keep you relatively stable, even when there's pretty high winds and a lot of chop around you. So you've got to decide like, what's important to you? What are the hills you're going to die on? What are the lines you're not going to cross? What are your values that everybody can come to rely on and see you as being predictable in the best way? And that is a long conversation that people need to have with themselves. And so to me, like, that's one of the things that this moment that we're living in, I think demands from leaders.

5:23Yeah, and it really describes how you start with that first really big question is, do you really want to lead? And to me, that's so compelling because so many of us are accidental entrepreneurs. and so many of us, even within organizations, had leadership opportunities thrust upon us or opportunities for advancement showed up and we raised our hand or maybe we didn't. Maybe we were put into those places. And maybe some of us didn't really ask for this or really have had time to do that kind of work to really reflect on what we value, what's important and what our vision is for the way we wanna be in the world.

6:05Exactly, and to your point, And I do think that a lot of people end up in leadership positions through a whole bunch of circumstances, right? But find themselves in these roles that maybe there's a little bit of like, wow, I did not know that this is what I was stepping into. Because leadership is, these are hard jobs, right? I mean, you're dealing with people problems all day long. You're putting out fires. There's no time to do work at work. So you're doing that in the early morning or late at night. And I think sometimes people get into leadership positions and go like, I had no idea. And they're not able to do the things anymore that they're really good at, that they enjoy doing.

6:43And so that's why the first section of the book is called, Do You Really Want to Lead? And the word really is italicized because I just encourage everybody to really take the time and say, do you want to do this? And also do as much as you can to find out what the job is going to entail. Talk to people who are doing it now and ask them, like, what is it like? Because I'm often struck by, I mean, now, like with kids graduating from high school, just the phenomenon of the college tour, right? Like you got to go visit 10 colleges and parents are asking their kids, like, how do you feel about how you feel?

7:18And do you think this will be a good fit? And yet, so there's all that sort of rigor around that process. And yet people step into big jobs without doing the same kind of research and trying to figure out whether it would be a good fit. So this question of do you really want to lead, to me, it's one of three core questions that people need to ask themselves. So one of them is do you really want to do this and are you clear-eyed about what it entails and your motivations? Another core question I think people need to wrestle with is, what to you is the difference between management and leadership?

7:52Because there's no cookie-cutter answer to that. But you should be clear in your mind what the answer to that question is so that you make sure you focus your energies on the leading part, not necessarily the managing part. And then the third question is what I mentioned before is the simple question of who are you as a leader? And I always tell people, you will probably go through your entire career and nobody will ever ask you the question, who are you as a leader? But I think there's a really good return on investment of when you put in the time to figure out, well, how would you answer that question?

8:26And I think if you are thoughtful about it, think about, say, your three or four core values, why they're important to you, the stories about how they became important to you, what they look like in practice. I think just knowing the answer to that builds self-awareness. It builds that magical quality of executive presence, that sense of calm and confidence that I think every leader should aspire to have. That's so true. There's so much in there. I really am curious because you've spoken to, as you've said, thousand plus CEOs over the years and really honed in on these ideas. So I have to put question two back to you because what is your personal definition of the difference between management and leadership?

9:10To me, I use the metaphor of a playbook. So I think to be a manager, there's a little bit of an expected outcomes that somebody is giving you. So the boss comes to you and say, look, we've got this project. We know what we need you to do. We know what good looks like. We know what the outcome is. And we're giving you resources, people, time, money, et cetera, to execute this kind of pre-existing, like figure out the playbook a little bit, but we already know what we need from you. And so that's to me what management is. I think leadership is to, first of all, really execute the management part of it well, because you have to do the core function of managing well to be a great leader.

9:48Do it really well, but then start just the questioning process of, say, how can I make this more efficient? How can we optimize this? How can we transform this? I have this role. I have this job description. How can I completely reinvent this? And then start looking at your boss's plate. Can I take some stuff off my boss's plate? Can I look around and see opportunities for the company that I'm going to have the courage to raise my hand and say, we should try this? And maybe there are problems that the business, the company has that they don't even know about. And so, it's just that you got to master the core job, but then always be looking at how do I transform this?

10:29Where are the opportunities? How can I go above and beyond that sort of playbook and help the company write the playbook? To me, and again, we could talk about this for hours, but that's the one I gravitate to. That is a very specific mindset. I like the phrase, in most companies, there's passengers and there's drivers, right? Like a lot of people just want to join a great company and kind of be passengers in the backseat. But then there's people who have this driver mentality. They want to contribute. They want to help lift the organization and their team. Adam, I wanted to back up just a slight bit to cover one thing regarding, you mentioned the history of management and the history of leadership and going back in time and things have changed.

11:17Can you highlight some real differences between leadership a decade, two or three ago, and the new skills and requirements that have changed for this time period? What does it look like or what have you experienced? Yeah. So I think leadership was a lot easier when you go back decades, right? It was much more of a top-down militaristic. The world was more stable and predictable. And the function of business and management leadership in some ways was to sort of optimize what you were already doing, right? That's the sort of Six Sigma and lean manufacturing and all those things. And so now I think, again, I keep coming back to this idea that leadership has gotten a lot harder.

11:59And then you ask yourself, well, why is leadership so hard? And the framework that I use and the way I like to think about leadership is that it is a series of balancing acts or paradoxes or contradictions. And I always tell people, if you're setting out to learn how to manage and lead people and you start buying books and reading articles and things like that, I always tell people get a neck brace because you are going to get whiplash from all the contradictory advice out there, right? Because everybody's telling you, you know, lead from the front. Now you got to lead from the back. You got to create a sense of urgency, but be patient, right?

12:35We're hearing a lot about compassionate leadership right now. People are going through a lot. You have to be compassionate, but you also have to hold people accountable and make sure that they're driving performance. And so, to me, part of the art of being a leader today is understanding that all these paradoxes, these contradictions, those are not or propositions. And if you find yourself thinking about, well, am I supposed to do this? Or am I supposed to do that? Or am I supposed to act like this or that? You have to understand that it's not an or proposition anymore. These are and propositions.

13:09You need to do both. Not at the same time, but you need to understand that leadership is a balancing act and then be able to flex based on what the moment demands because there's sometimes you need to really listen and make sure that your team is heard, get all the input. But then there's also a moment where you really need to be directive and say, hey, everybody, this may not be a popular decision, but we're going to go left. We're not going to go right. But I want you to know I've heard everybody. And so to me, that's what leadership is about and why it's so hard. But I think that paradox is balancing acts, contradictions, if you will, provides a little bit of a handy framework for you to diagnose whatever challenge you're dealing with about leadership at any particular moment.

13:53That's some great insight. Appreciate that so much. One of the things that comes to mind is everyone has their favorites, if you will. I'm curious, are there any current favorites that you have as far as leaders as examples? I don't because I feel like, look, we all know the sort of well-known leaders out there, but you never quite know how the person acts day to day matches the publicity around that person, right? So it's hard to know. Maybe a better question is, who are you watching these days? Well, I'm intrigued by the big brand name CEOs, just like everybody else is. I think it makes for interesting reading.

14:33There's some big personalities. You know, everybody's reading about Elon Musk these days. and others. And I will say that my approach to understanding leaders is, and I use this in pretty much every interview that I do, is to really ask questions about their early years. You know, when they were a kid, who raised them, what were the circumstances? And I bring this up because I think we need to acknowledge that, again, I'm repeating myself, but leadership is really hard. And I think there's a simple question of like, why do people want these jobs, right? I've interviewed a number of people over the years and this phrase comes up often that people are drawn to the fire, right?

15:14And so, just there's a sort of big complicated problem and they are drawn to that, whereas other people might feel like they want to run from that because like, that's like, why would I put myself through that? And so, I'm always intrigued by like, what motivates people to take on these jobs? And I've done a little bit of my sort of, it's a qualitative database, right? All these interviews that I've done, but some of the patterns to me are pretty clear. And I'd say that one bucket, if you will, is that there's just people faced a lot of adversity early in their life, right? And for whatever reason, that adversity, it spurred them on to want to have a greater sense of control of their sort of destiny of their life.

15:56And that motivates them to have these jobs. And another common theme is some version of sort of the immigrant story, right? Maybe they're children of immigrants and that they were the first in their families to always be doing new things. And that, frankly, just becomes their comfort zone. So leadership challenges are just another new path. And they've been on the new path for a long time. And so those are a couple of the common themes. But when I'm watching leaders and trying to understand their behaviors, I always do want to go back into the early years and try and figure out like, where does that drive come from?

16:29Where does the stamina come from? What are they running towards? What are they running from? Because we're all a combination of those things. And it really speaks to your earlier question about, you know, who are you as a leader and what do you value? And in that reflection, I think it can be helpful to look back and try to understand what are the things that make me tick? Why do I show up in this way? You know, what's caused me to gravitate towards these positions? Yeah, and I think there are limits to how much we can shrink ourselves, right? And there are limits to self-awareness. But there's a key insight from one CEO that I interviewed, this young woman named Layla Janna, and she died tragically a few years ago.

17:09But when I interviewed her, she was telling me about her upbringing and it was really tough childhood. I mean, she moved a lot, was really bullied at school, really rough relationship with her parents. And yet she seemed to have this incredibly positive attitude. And so I asked her, like, where do you get your positive attitude from? And she said five words that I've never forgotten. She said, reality is just source material. And what she means by that is like we go through our lives, we have experiences and we sort of say, okay, well, this is reality. This is our reality. But I think we need to be aware of the fact that we are telling ourselves a story about our experiences, that we are, in effect, writing history books about ourselves, or editing film, if you will, about what we just went through to create a story.

17:58And I think that insight alone lets you and helps you step outside yourself and just ask the question, well, what story am I telling myself? And as leaders, you need to beware of certain traps. It's not just leaders, but just as human beings. Like there's the victim trap that people fall into. I mean, stuff could be going wrong with the business you're trying to build. And you start thinking like, why is this happening to me? And that's the victim narrative. And that's not productive, right? Or there's the unfairness narrative that sometimes people have. And that's not productive either. So to me, that's a really key insight just around self-awareness.

18:35And again, you can hire a professional to help you with self-awareness, but I think you can do a lot of work on your own. Yeah, and I think a lot of that speaks to surrounding yourself with other people that will challenge your ideas, right? And that can help identify those stories, even within the workplace. One of the challenges that seems to emerge is that we know that many great leaders, specifically like to surround themselves with people that will check their biases, right? Not everyone, but many great leaders do use this type of a technique. But just to build on your point, there's a very specific tactic that I heard from one leader that I thought made a lot of sense because your point is well taken.

19:17Everybody has their blind spots, right? But one leader I interviewed, she will say not only to her board, but to her executive team. She just says up front, I have blind spots. Everybody has blind spots. It is your responsibility to help me work my blind spots. So essentially, she's sort of saying, this is part of your job. I'm not just asking you to give me feedback or anything like that, but just to say, this is your job to help illuminate my blind spots. So I mean that right in and of itself, what a leadership lesson there, right? Just that tactic of naming that and setting that expectation.

19:53Because, you know, the flip side of that is, it's also my job to name those for you. Exactly. When we wonder, how do we develop the next generation of leaders? Every leader says they want more. I know that you talk to a lot of corporations, a lot of boards, a lot of CEOs. Part of what this book speaks to is being a tool to help others that aspire to being the next generation of leaders. How are they thinking about this challenge? Yeah, it's a great question. And full disclosure, I work for a consulting firm that does leadership development. That said, in our work, I think one of the insights that we hear often, whether it's from boards or leadership teams, is that the historical thing that people have looked for in leaders and high potentials and upcoming is that sort of domain expertise, the technical expertise.

20:47Like, can they drive performance? And I think there's this sort of awareness recently. It's like, wow, like all these soft skills, right? And the soft stuff is the hard stuff. But the authenticity, the humanity, like, do people trust this leader? Are they good communicators? People are suddenly realizing, wow, that's just as important as the hard stuff. And when they find a leader, they sort of latch on to them, go, boy, this is the person. And I think there's a sort of growing recognition that we need to have more of a almost infrastructure, leadership development infrastructure that teaches both the hard stuff and the softer stuff.

21:28And in some ways, I think business schools are reflective of that because their roots are in the hard stuff, the accounting and all that. But I don't know if any business course or business school has a course on how to be a better listener. but I think every business school should have a course on how to be a better listener. Couldn't agree with you more and I think we should banish the term soft skills. It would probably take a long time to make it go away but in it of itself I mean that's just such a negative connotation for what may be one of the most important disciplines. Exactly yeah and we've talked about this for a while but the words that I would like to get rid of I mean I think it would be an interesting thought experiment if the entire business world stopped using the word strategy and instead replaced it with the word bets.

22:17Because to me, in this era of so much disruption and unpredictability and instability, that we need to be more honest with ourselves and as leaders and with our teams is that what companies do is they make bets. They call them strategy, but strategy documents are often highly polished with spreadsheets that go out 10 years and projecting profits down to the penny, right? And the world doesn't work that way. And it's not just any bet. Let's put down a random bet. It's an educated bet. It's an informed bet. But I think every company is in some stage of transformation. And one of the challenges of transformation is getting people up for that journey, like recognizing that there's some risk here.

23:00And I think one of the ways you get everybody on board with the idea of like, there is risk involved in what we do is to call things bets. Because again, I just keep coming back. Companies make bets, right? They're betting on consumer behavior, macroeconomic forces, whatever it is, they are making bets. And to underscore that, I always make the point is like, imagine being in the pitch meeting when Airbnb, the founders were pitching to VC firms. It's like, strangers are going to stay in strangers' homes? I don't think that's going to happen. Well, Well, it turns out they will. Or Uber, strangers are going to get in strangers' cars?

23:36I don't think so. Well, it turns out they will. And that's what companies do. They make bets. Sometimes they pay off and sometimes they don't. Yeah, and that leadership mindset of recognizing that and putting that into your language. Because you have to set that tone for the game that we're all playing, right? The other thing that I'm hearing in there, or at least that it's making me think about, is by calling it a strategy, it's almost like you're suggesting that it's going to lead to a knowable outcome. That's the fallacy there, right? It's like, you know, you're making a bet just like a coach is going to come up with a strategy for a specific game and it's going to be based on tendencies.

24:15This is how we think the opposing team will act based on the film we've watched or what we see, right? But in the business environment, you're working with so many different variables. And so often, despite your best efforts to learn more about the other players in the marketplace or the folks you're trying to attract and sell to, you're just never going to have perfect information. So at best, as you said, you're trying to reduce that probability. But make no mistake, the risk is definitely there. Yeah. And it's like the sort of dated cliche of business is the glossy business magazine cover shot where, you know, and we all know we can see it in our mind's eye, right?

24:53right? The CEO, their arms are folded across their chest and this look in their eye and the whole image is like, this person sees the future, right? Like they've got so much confidence because they know they can see around corners and it's like, nobody's buying that anymore. And I think one way to build a sense of cohesion and teamwork is to have a more honest conversation. Like nobody knows, right? You just, you make informed and educated bets, ideally based on data and analysis, but at the end of the day, it's a bet. Yeah. And being willing to name that and accept this idea that you're not always going to know, right?

25:32And that's part of the process. So, I mean, there was one part of your book that was really compelling when you talk about this stoplight thing where you find yourself at the stoplight, like you're faced with such a big problem. And everyone listening right now has been in a case where they have found themselves in a situation where they got some news that was so bad that they thought it might jeopardize payroll, the kind of stuff that keeps you up at night, or you just lost your biggest account, or, you know, what are we going to do? Or this piece of information that could turn the company inside out is going to become public.

26:05What are we going to do? And in that moment, you don't have the answer. And the way you describe it is, you know, you're at the stoplight, and it hits you or you get that call, and the light turns green, and you're still sitting there because you're just almost frozen in that moment. And I think one of the sub themes of that challenge and you described for business owners trying to make payroll and stuff that I think one of the challenges for all leaders and business owners is like how much of the challenge do you fully absorb and act as a buffer for all your team to kind of protect them? And how much do you share with them?