Episode 369 – The Leap to Leader with Adam Bryant

Adam Bryant‘Everything at its core has to be one of those three things: a great insight, a great story, or a great practical approach.’

Adam Bryant, creator of the New York Times‘s Corner Office column, has interviewed a LOT of top leaders, but not in the way they expected. He ask them about leadership, rather than strategy, and their own leadership in particular: questions that allow them to articulate answers they haven’t seen before. 

In this fascinating conversation we explore how he’s built on this journalistic approach to write a series of books, and how writing in public builds credibility, expands networks, and creates a perpetual motion machine for authorship.

If you’re interested in leadership and writing, and if you love a good metaphor riot, this is unmissable. 



Adam’s website: https://adambryantbooks.com/

The ExCo Leadership site: https://www.excoleadership.com/

Adam on LinkedIn: https://www.linkedin.com/in/adambryantleadership/

Adam on Twitter: https://twitter.com/AdamBBryant

Alison on Twitter: https://twitter.com/bookstothesky

The 10-day Business Book Proposal Challenge: http://proposalchallenge.com/

Power Up Your Writing workshop at Gladstone’s Library: https://www.eventbrite.co.uk/e/power-up-your-writing-workshop-tickets-600773689277

WriteBrained: A 28-day exploratory writing adventure: https://pi-q.learnworlds.com/course?courseid=writebrainedcourse

The Extraordinary Business Book Club on Facebook: https://www.facebook.com/groups/1447064765612358/

Alison Jones: I am here today with Adam Bryant, who is Senior Managing Director and Partner at the ExCo Group, where he works with hundreds of senior leaders and high potential executives. He’s the creator and former author of the iconic Corner Office column in the New York Times, distilling real world lessons from hundreds of interviews with top leaders, and he’s the author of The CEO Test: Master the challenges that make or break all leaders and The Leap to Leader: How ambitious managers make the jump to leadership.

So first of all, welcome Adam, very, very good to have you here.

Adam Bryant: Thanks so much, Alison, appreciate it.

Alison Jones: And congratulations on the new book in particular. How’s that feeling? What stage are we at?

Adam Bryant: It’s launching in about two months, so yes, it’s exciting and as you know, writing books is a long process and take a lot of work.

Alison Jones: Well, and let’s dig into that, shall we? Because in your case particularly, it’s not as if you are manufacturing something from the depths of your soul uniquely. You are very much drawing lessons from the people that you speak to. So tell us about that process. What’s that like?

Adam Bryant: Sure, and just to provide a little context, my sort of the start of my journey, if you will, into leadership really goes back to 2009. So I spent most of my career as a journalist, as a reporter, as an Editor at the New York Times. And when I was a business reporter, I interviewed a lot of CEOs and I realized over time that CEOs are interviewed always the same way in the business press, which is kind of as strategists, right? Most of the time CEOs are asked like, you know, what’s your strategy and what about the competitive landscape in your industry, et cetera.

And I just found the more time I spent with CEOs and other leaders, the more I just wanted to ask them like, how do you do what you do and how did you learn to do what you do? So I rolled all that up into this very simple, ‘what if’ in 2009, which is what if I sat down with CEOs and never asked them a single question about their companies? And instead asked them about leadership and lessons they learned and early influences in their life and how they think about teams and culture and hiring, these sort of more universal themes.

So that launched the Corner Office series I did, which I did for about a decade at The Times, 525 interviews, never missed a week. Didn’t intend to start writing books, but just as the sort of the interview count kept growing, I just started noticing patterns and sort of started seeing, wow, there’s an interesting question at the core of this. And then the answers are here.

So that provides a bit of context. Since I left the Times about 6 years ago to join my current firm, I’m sort of went all in on LinkedIn. I’ve got four different interview series including with CEOs, Board Directors, Heads of HR at big companies. Again, all with this very tight swim lane of we are only talking about leadership. We’re not talking about company strategy.

And so my approach to leadership is journalistic, with a small j, I don’t wake up in the middle of the night, you know, I have a dream about a new Venn diagram that explains everything about leadership. I talk to CEOs and other people on the front lines who are figuring out this crazy world that we’re in and how to lead within it.

And then from those interviews, those become my sort of dataset, the reporting that I use for the books and the thing I try to to do with the books to say, okay, I’ve got all this raw material from these, by now more than 1000 interviews. Then my process is to, you know, once I come up with a sort of core idea of the book and then maybe the framework, then I just go through all my interviews again.

And I buy index cards by bulk, literally a pallet of index cards shows up on my doorstep from a truck. And that’s kind of my very old school process. I’ll go through the interviews, when I see a quote or a story or some kind of framework that speaks, that helps inform the framework that I’ve figured out for the book. I’ll just make a note of it and throw it in the pile.

And then by the time I’m done, I’ve got a really high stack of index cards, and then I just go through them and I start sorting by category. And so by the time I actually sit down to write the book, I have all the raw material there in effect, and it’s kind of in the right place.

So, very old school I know, but it works for me. I’ve written four books and I keep coming back to it as…

Alison Jones: I’m a huge fan of index cards, as anybody listening to this will know if they’re a regular listener and there’s something about the thingness of them, the way that you can just sort of spread them out in front of you and sort them. But also the act of writing, you are forced to distill the key point because it’s quite a small card and you write it by hand, which fixes in your head, and you have to categorize it.

And all of those things are valuable cognitively, I think.

Adam Bryant: Yes, completely agree. And then you can also with index cards, you’ve got the benefit of being able to really spread out on a big space, right? Your dining room table, or in my case, my ping pong table up here in my loft.

Alison Jones: You can’t play ping pong at the same time as writing a book. That’s interesting to know.

I want to go back to the interviewing because it’s really fascinating and actually not dissimilar to, it’s not exactly the same of course, but I talk to authors about their books and we talk about the topic that the book is on, but then very quickly we get to the writing of the book, and often we’ll get to the end of a conversation and, you know, we switch the mic off and we’re in the green room and they’ll say, ‘nobody’s ever asked me that before. I really enjoyed that. I hadn’t really thought about…’, and so, there’s some real joy isn’t there, in getting people talking about stuff that they aren’t usually asked about and where they’re almost having to articulate the answer to themselves as well as you.

So tell us a little bit about how you draw that out of people, but also how, because you’ve heard so many, so each one, it’s unique because it’s a unique individual, and it’s an exemplar of themes you will have heard before.

 What does that, how does that look when you’re doing it?

Adam Bryant: Sure and a big part of it is I am asking the CEOs and other leaders questions, and I’m not saying nobody ever asked them these questions, but very few people do, because I think, especially if you’re a CEO, you probably spend your day giving some version of the same speech 20 times over, right? Whether it’s to employees or investors, other stakeholders, and so, when I interview CEOs, I will often say to them, as part of my preamble, I’m not going to ask you any questions about your company. And a lot of them just say, thank you.

Alison Jones: Oh, what a relief.

Adam Bryant: And there’s a weird gap I find because, you know, strategy is something that, I know it’s an iterative process and stuff, but strategy is a little bit more of an event, right? Like you figure out your plan for the next year or two, whatever it is, then you work the plan. But the thing that CEOs think about literally all day long is leadership: their own leadership, how to grow leaders and develop leaders, how to get their team operating more effectively, how to build a high performing culture. But nobody ever asks them about it. So on the one hand, they are very happy to have that conversation. Excited that, it’s sort of like you imagine a football coach or something like, coaches are just always asked like, are you going to win on Sunday? And why did you lose last Sunday? Right? Nobody ever asks coaches what’s your approach to leadership? Even though that’s what they think about all day.

So when I created the series, it was this great little laboratory. Every single week, every single interview, I could try out new questions, just to see, you know, is there, does this, maybe not every time, but lead to a good insight. And part of the goal is to get these leaders off their talking points. It was always nice to me when I would hear, and I did, certainly pre pandemic, all the interviews in person. It was always nice to hear from the communications person or public relations person in the room, ‘I couldn’t prepare my CEO for this’.

And it’s like, that’s precisely the point. And I found that some of the most revealing questions are the ones that were focused very much early in their life. So often I would ask people what were the early influences that really shaped who you are as a leader. What kind of things were you doing outside of school, when you were in middle school and high school years? Tell me about your parents or whoever raised you. How have they influenced your leadership style today?

And I have found that generally with those three questions, if somebody goes into that conversation, being candid, open, and honest, by the time I have the answers to that, I feel like I’ve got about 85% of what I need in terms of: Okay, I understand you as a human being. And just through that questioning, you hear these heartbreaking stories of adversity they faced when they were younger. Or I’m always curious because these top jobs, especially CEO jobs, they don’t make any sense on paper. Like if you look at a job description for a CEO, other than like if you take away the power and the money, which some people are really motivated by, like, why would anybody do those jobs, right? They’re 24/7. You have to make it so many sacrifices and trade-offs in your personal life, the weight of responsibility on your back.

So I’m always intrigued, like, where do you get your drive from? Where does that come from? And so that’s one of the things I’m trying to answer. And so as much as I’m really trying to understand their insights about leadership and the stories about how they learn them in some very tactical and practical approaches to leading more effectively, I’m really trying to understand them as human beings.

And I just find through those questions and what was interesting to me is my interviews are sort of like open source software. If you want to prep for one of my interviews, it’s not like there’s a black box, right? The questions are all there, but I was always surprised that, you know, the number of times I would ask somebody tell me about your parents and how they influence your leadership style today, you could tell that they had never been asked that before. Never thought about that before. And some of them actually got quite choked up because they hadn’t really thought about it before. Maybe they saw the question in the interview prep or something, but really sort of engaging it was very emotional for all of them.

And to your point, my best interviews, the ones that I enjoyed the most, was where it did feel like they were connecting dots in real time and in their own lives, it’s like, ‘wow, I just realized the reason I do that in meetings is because of that’. That was always fun for me.

Sometimes I would interview these, you know, super famous CEOs who had written four books and they already had their talk tracks, right? It’s like, ‘okay, that question, I’ve already written that chapter and so I’m not…’ and that was great, good stories and stuff, but the very cool moments for me was interviews that felt like an act of creation rather than just I’m going to play you my greatest hits.

Alison Jones: Yes, I love that. And there’s something about that journalistic background of yours. That license to ask the questions, that zeroing in on the human story, that I’m finding really interesting as well because obviously most of the people I speak to are business leaders rather than journalists.

So I guess for somebody writing a book, I am going to ask you your best tip later on, so I don’t want to preempt this, but if somebody’s writing a book, what can they take from the journalistic approach that you think would be valuable for anybody to use?

Adam Bryant: Yes, well, at a very practical level, I mean, if you’re going to write a book, I mean, maybe it’s all based on research and you don’t need interviews, right? You don’t need sort of anecdotes or stories to bring them to life. But I think with social media today, the sort of machine that I’ve built, and it all makes perfect sense in hindsight, you know, you’re sort of bumbling along, figuring stuff out…

Alison Jones: I totally had this all planned from day one. Yes.

Adam Bryant: …but the interviews that I do, at The New York Times and now on LinkedIn, where my interview series have pretty big followings, I do the interview and I always do a pretty drastic condensation. So the transcript will come back and it’s typically seven to eight to nine thousand words, and I’ll boil it down to about 1500.

And that accomplishes a couple of things. First of all, there’s kind of an immediate payoff for the person I’ve interviewed because I think it’s a much more attractive proposition to approach somebody and say, I’d love to interview, by the way, I’ve got this series on LinkedIn. It’ll probably appear like two or three weeks. And they get the immediate gratification of, oh, there’s a good payoff of that time.

And then, maybe two years later I reach out to them, you know, it was such a great story you told me in that interview. I’d love to use that in my book. I hope you’re okay with that. And they always say, yes, of course.

But I think, just in this day and age, it’s much easier to make that pitch than approach somebody to say like, I’m working on a book, might come out in about three years, you might be quoted, by the way, can I have two hours of your time? Right? So I think that’s a good tactic and it does create this sort of perpetual motion machine of, you know, you’re building your profile through these interviews.

It becomes a calling card when you reach out to people, say, Hey, I do this interview series. We’d love to get you in there. And then again, down the road you can use them for the book.

Alison Jones: And each time of course, the person’s sharing it and you are getting in front of their network as well. So that is quite powerful, isn’t it?

Adam Bryant: Exactly, and it is informing my thinking because it’s not… the way I write books is that when I sit down to write the books, in effect, I’ve done all the reporting. I’m not saying like I’m a hundred percent done and I will continue doing interviews. There may be a new insight, but at that point it’s, I have in effect what I need and very often the ongoing interviews are always knocking my head around in a good way to sharpen my thinking about the book. So again, it’s a little bit like, I don’t know what the right metaphor is, you know, maybe it’s surfing, but being on the right part of the wave rather than sort of getting in front of it and then trying to think, wow, I need all this reporting and starting from scratch.

So again, it works really well for me, but at the core of it is just this idea of talking to leaders about leadership, not about their organizations. And the other tip that I will share is, and this is in the context of leadership, and maybe it’s true in other fields, but having spent about 12, 13, 14 years in the leadership space now, I’ve come to the realization, and I know this is going to be a shocker, but there’s a lot of kind of hooey in the leadership space, right? There’s a lot of sort of, I know, I know you’re surprised, right? You know, there’s a lot of fortune cookie wisdom and there’s a lot of people saying, people love to put adjectives in front of the word leadership to sort of create some new idea and usually it’s, you know, you sort of want to say to yourself, well, as opposed to what?

So given all that, I think it’s important to ask, if you are going to talk about leadership, how do you do that in a way that is useful? And so what I come down to, or my argument is that there are three currencies of leadership, an effective leadership conversation.

The first one is insight. Tell me something that helps me understand the world and human beings better in organizations. Just something that feels like a vitamin, where it’s like, wow, I suddenly understand that dynamic better. And it might be the first time you’ve heard that insight. Or you’ve heard it before and it could be a really timely reminder of something. So that’s currency one.

Currency two is stories. Tell me how you learned this insight, like, paint a picture for me. I was first time manager when I was 20 and I kept doing this with my team and they basically pulled me… so that kind of story, it makes it feel real. We’re wired as human beings to remember things through stories.

And then the third category is make it practical, make it useful. Give me a tactic, an approach, a framework, a tool, a technique, so that when I go back to my job on Monday, I can put this idea into action. And so when I do the interviews, I’m looking for those. When I condense the interview, I’m cutting out all the platitudes and the generalities.

And so by the time I’ve got my database of reporting, everything at its core has to be one of those three things. A great insight, a great story, or a great practical approach.

Alison Jones: I love the way you described this as the currencies, that’s exactly right. And of course that you don’t use one in your business book, you interweave all these, they actually work really well in combination as well.

You said earlier that you hadn’t planned to write a book. I’m misquoting, but it was something like that.

What was the journey where you suddenly went, I mean, was it as simple as, oh, I’ve got enough material, I might as well write a book? Or was there something that made you think, actually a book had a different kind of place in the content ecosystem and you wanted part of that?

Adam Bryant: Yes, and again, when I started the Corner Office series, it was just like, what if I started interviewing leaders and didn’t intend to write a book. But I think a few things happened and I’ve now written four of them. So the same thing keeps happening, which is, to me it starts with figuring out what the question is, not the answer.

And it’s got to be at a sort of post-it note level of being concise and clear. And when you figure out the right question and then you say to yourself, I actually don’t know the answer, but I think the answer is in here and your gut tells you that you’ve got enough material that you can answer that question even though you don’t know exactly how you’re going to answer the question.

To me, that’s the sort of moment. And then, look, I don’t need to tell you, writing books is really hard. You know, the metaphor that I use just in my head when I’m starting on a book project, to me it feels like you’re standing at the base of a mountain and you’re looking up and you say like, okay, here we go. And you start climbing. You don’t know how high the mountain is. You don’t know how long the mountain range is that you’ve got to get on the other side, you know, you’re going to have a lot of bloody knuckles. And there’s going to be a lot of moments where you’re asking yourself, why am I doing this, right?

And you’re going to get really far and then realize, oh no, I’ve been spending the last three weeks on this thing and I’m solving the wrong problem.

Alison Jones: It’s the wrong mountain.

Adam Bryant: Yes, exactly. And then a year later, whatever, you get to the other side. And so, and I use that just because for anybody writing a book, you have to be so invested emotionally in it that you are going to get through those really dark periods and there’s frustration and double backing and realizing that everything that you just did for the last two weeks doesn’t work.

So you have to be very clear on what you’re doing, why you’re doing it. And for me, when I’ve gotten those right questions, that to me it, there’s a little bit of a feeling like, and I know I’m mixing metaphors, but there’s a little bit of a feeling of, they’ve grabbed me by the throat and I can’t really let go. Like, that’s a really good question. I don’t feel, I know people may have tried to answer that before, but I don’t feel like they’ve really grappled with the question.

And so that’s the thing that excites me and ultimately what sort of, why I do this, is because, first of all, I think there’s too many bad bosses in the world. Second, I think a lot of bosses and leaders could be even better. And if they are, just think about the sort of exponential lift from good managers and good leaders, not only on people’s individual lives, but on their organizations. And so what I’m trying to do is just, I’m really just trying to share insights and stories and wisdom.

I heard an expression from a CEO years ago that he says he likes people who are information socialists, that they like sharing their knowledge rather than hoarding it. And so…


Alison Jones: than an information capitalist. I love that.

Adam Bryant: Yes, so I know socialism’s like, you know, people have a, but what I mean in this context is like I try and learn a lot about leadership, but it’s not doing any use sitting inside my head, I try and share it.

Alison Jones: And that’s the thing about ideas. They work in a very different way economically than any other goods.

Adam Bryant: Exactly,

Alison Jones: Yes, brilliant. What was the question that you were grappling with that that lit you up for The Leap to Leader?

Adam Bryant: It’s sort of captured in the title of the book, like what does it mean to make the jump from being a manager to a leader? And so what does that mean? And then how do you do it? And, you know, it’s interesting, like life is so serendipitous, right? You can’t plan for things. And I probably started working on this book about a little more than two years ago when we were, you know, hip deep into the pandemic, right?

But the timing of it right now, so we work with a lot of companies of all sizes, but one of the most universal themes we hear from our clients is that they need everybody to step up as a leader. They need their managers to figure things out. The days of waiting for somebody to hand you a playbook on how to do what you’re doing, those are gone.

And every company needs everybody to help write the playbook together. And there’s all these, you know, new challenges and we could go on for hours about this, but I think managing and leading has gotten about five to ten times harder. Pick a number. And companies need everybody to lead from their seat.

So, I just became really intrigued by like, is that something you could teach somebody or show somebody? Again, through insights, stories and practical tools and approaches, this is what it means to be a leader, the mindset shift you have to make. And so that became the sort of, you know, hand around my throat that wouldn’t let go and really wanted to answer it.

And I know I sound like I’m doing an ad for the book. I’m not doing that. I’m just saying sometimes books are incredibly timely for reasons that are beyond our control. And right now I’m enjoying the feeling that there’s a tailwind at my back.

Alison Jones: And just to go back to the mountain metaphor for a minute. If you are writing a book and it does feel like climbing a mountain, it’s quite lonely, if you’re just doing that. And one day you’ll be at the top of the mountain, you’ll be publishing your book, but the way that you do it, in public with those mini milestones of each interview of those, you know, the posts that you do, it’s almost like looking and enjoying the view at each sort of new stage up the mountain, isn’t it?

It’s a much more rewarding and much more stickable process. You’re doing it in small increments rather than one huge manuscript.

Adam Bryant: Yes, and to that point, I mean, probably memo to self, I should probably enjoy the journey a little bit more. But you know, books are kind of all consuming and when I’m in the middle of it, you know, I find it very hard to turn my brain off. Like I’ll be walking the dog at 5:30 in the morning and trying to solve that particular Rubik’s Cube of puzzle of, you know, figuring out how to get into that chapter and so it’s one of those things, like on the one hand, you’re in the middle of it, there’s part of you saying, man, it’d be nice when this is done. On the other hand, when it’s done, you sort of feel like, you know, it’s like I need another Rubik’s Cube for my brain. So I’m probably oversharing.

Alison Jones: It’s so funny you say that. I was just having that conversation before we spoke, actually. I was like, because my book came out last December, we’re in May as we speak. And I need another book sized project because there’s nothing like it to engage you creatively and thoughtfully and deepen your practice and yes, it’s really interesting, isn’t it?

Adam Bryant: Yes, my wife was joking with me the other day because I’m, you know, the book’s launching in a couple of months and I’m just mostly going through like, publicity stuff. And she turned to me the other day, she goes, are you starting to think about your next book? I said, no. And she goes, you are.

Alison Jones: You are, aren’t you?

Adam Bryant: But I’m really trying not to.

Alison Jones: Will you never learn?

Adam Bryant: I’ve got a good friend of mine who writes books and we talk about this shared problem that we have. And the metaphor we use is…

…well, the metaphor we use is like we have wood chipper brains, which is like, they’re always on, and you’ve got to feed a lot of wood into the wood chipper because if you don’t, your arms and legs are going to get it caught in it.

 And so there’s this kind of like wood chipper thing where like, I need big ideas and big problems to solve. Because I think in many ways writing a book is kind of like solving a problem, like figuring out a puzzle. There’s all these pieces, how do they fit together in a satisfying and organic way that makes sense.

So maybe it’s like a puzzle addiction. I don’t know what it is, but again, I’m probably oversharing.

Alison Jones: I love the idea that, you know, I have to keep the ideas coming, otherwise it’ll consume me, quite literally. And I also love that we have such a riot of metaphors going on here. Somebody’s going to do a taxonomy of the metaphors that we’ve used, and it’s going to be amazing.

I want to know your best, your recommendation for a book that you think people listening should read. It’s not allowed to be Leap to Leader, obviously, or The CEO Test, but which book would you recommend that people listening should have a read of if they hadn’t?

Adam Bryant: I love the book In the Heart of the Sea and I love sort of adventure, whaling books, just stories about resilience. And in terms of leadership books, I mean, there’s a lot of the ones that people usually mention, but I will recommend Bob Iger’s book The Ride of a Lifetime about what he did at Disney.

A lot of CEO leadership books are just victory laps and they’re giving shout outs to all their buddies and stuff. But there’s just a lot of really good and nuanced insights about leadership in that book, with really powerful stories that bring them to life about, you know, his meetings with Steve Jobs and how he landed the Pixar deals.

So I just really enjoyed that book

Alison Jones: That’s great. I haven’t read that one.

And you’re right, I do tend to shy away a little bit from CEO biographies, so that’s a great steer. Thank you so much.

Adam, it’s been fascinating talking to you. If people want to find out more about you, more about the LinkedIn series, more about the works that you do, the books and the articles, where should they go?

Adam Bryant: Yes, just reach out to me on LinkedIn with my name, you’ll find me there.

My books website is adambryantbooks.com. And our firm’s website is exco leadership, excoleadership.com.

Alison Jones: Amazing. I will put all those links up on the show notes at extraordinarybusinessbooks.com. Thank you so much for your time today. It’s been fascinating.

Adam Bryant: Great. Really enjoyed it. Thank you.

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