Steve Hills
Author and Former President & General Manager of The Washington Post
On the latest Walker Webcast, Willy sat down with Steve Hills, former President and General Manager of The Washington Post and author of the forthcoming book, The Alpha Trap, for a conversation about leadership, transformation, ambition, and the hidden costs of success.
They explored how Steve helped transform The Washington Post from a newspaper into a digital-first technology company, what that experience can teach leaders navigating the AI revolution, and why vulnerability can be a powerful leadership strength. They also dove into The Alpha Trap and what Steve learned from interviewing more than 100 high achievers about the relentless pursuit of status and success, the difference between being admired and being truly known, and how to bring the same energy we invest in our careers to our relationships, health, purpose, and fulfillment.
Watch or listen to the replay.
At a glance
1. Who is Steve Hills?
Steve Hills is the author of The Alpha Trap: When You Have Everything Except Enough, scheduled for publication in 2027, and the Founding Director of the Business Law Scholars Program at Georgetown University Law Center, where he also teaches. He previously spent 28 years at The Washington Post, including 13 years as President and General Manager, and currently serves on the board of AvalonBay Communities.
2. What are the top reasons to watch this webcast?
- Learn what Hills' experience transforming The Washington Post can teach today's leaders about adapting to AI and technological disruption.
- Hear why companies must protect their core strengths while simultaneously investing in the capabilities needed for the future.
- Understand what Hills calls "The Alpha Trap" and why the same drive that fuels professional success can leave other parts of life unfulfilled.
- Hear why Hills believes the growing difficulty of separating truth from misinformation poses a serious challenge and how AI could potentially help.
3. What can today's business leaders learn from The Washington Post's digital transformation?
When technology disrupts an established business model, leaders cannot ignore the new reality simply because they dislike it. Hills emphasizes the need to reduce costs where necessary while continuing to invest in new capabilities and protect the strengths that made the organization successful in the first place.
4. How can companies embrace new technology without losing what makes them successful?
The first step is identifying the organization's core strength. At The Post, journalism remained fundamental, but engineering became equally critical to delivering that journalism in a digital world. Hills believes leaders must communicate that new capabilities strengthen the core business rather than diminish the people and expertise that built it.
5. What leadership lessons did Hills take away from Katharine Graham and Jeff Bezos?
Graham demonstrated the power of humility, curiosity, and the confidence to be vulnerable, while Bezos was highly deliberate about identifying where he could add the most value. Despite their very different styles, Hills sees both as leaders who understood their individual strengths and led accordingly.
6. Why does Hills believe truth is increasingly difficult to protect?
Digital and social media often reward inflammatory content over nuance, allowing misinformation to spread quickly and reinforcing what people already want to believe. He views this as a serious problem for democracy but is cautiously optimistic that major AI platforms could give people greater access to factual information rather than simply reinforcing their existing views.
7. What is "The Alpha Trap"?
High achievers often spend much of their lives pursuing status, resources, professional success, and admiration. The trap emerges when those accomplishments no longer provide everything they want from life, particularly in areas like relationships, family, health, contribution, and inner fulfillment.
8. What surprised Hills most about the high achievers he interviewed?
Many successful men have effectively outsourced their friendships and social lives to a spouse or significant other, while the high-achieving women he interviewed tended to maintain stronger networks of their own. The distinction led him to examine how a relentless focus on achievement can diminish connection and vulnerability.
9. How can high achievers avoid letting professional success define their entire lives?
Hills encourages people to identify what they actually want rather than continuing to pursue achievement by default. His approach involves evaluating priorities such as work and wealth, relationships, family, health, contribution, and inner life, then intentionally directing time and attention toward areas that need more investment.
10. What can men learn from women about leadership and relationships?
He believes women tend to be more comfortable with vulnerability, asking questions, and maintaining meaningful relationships even while pursuing demanding careers. For men accustomed to projecting strength and competing for status, becoming more willing to ask for help, show uncertainty, and focus on knowing others rather than being admired can strengthen both leadership and personal relationships
Willy Walker:
Good afternoon, and welcome to another Walker Webcast. It is my joy to have my good friend, Steve Hills, join me today for a discussion about leadership, about media, about technological transformation, about Type A personalities, and sort of everything in between. I love having people like Steve on. Steve is very unique, and at the same time, just really smart people who have a lot of experience in leadership, in innovation, and at a time when our world and business leaders around the world are trying to figure out how to adapt and adopt AI, I think talking to Steve about what he did at The Washington Post back in the 2013, ‘14, ‘15 era is a really, really interesting sort of case study as it relates to technological adoption and innovation, and what made The Post a very, very early pioneer under Jeff Bezos' leadership. And then we will go into his book, which is all about Type A personalities, people who have been achievers their entire lives, and what are the costs of being a driven Type A leader, and what Steve has learned in his research on that book. Steve, let me do a quick bio, and then we'll dive in.
Steve Hills joined The Washington Post in 1987 as an advertising sales rep and rose to become president and general manager in 2002. He led The Post's transformation to a digital media platform and was named the most innovative media company in the world by Fast Company in 2015. Steve is a graduate of Yale and the Harvard Business School. He teaches a course on mindful leadership at Georgetown University, and is currently publishing the book we will discuss today called Alphaholics Anonymous.
Steve, let me start here. You worked for two iconic American business leaders, Katharine Graham and Jeff Bezos. I'm not stupid enough to ask you which one was either a better leader or a smarter leader, but give us a sense of what differentiated Kay and Jeff on sort of a day-to-day basis from all the other people that you've worked with.
Steve Hills:
Sure. It's a pleasure to be here, Willy. First, a small correction. It's now The Alpha Trap.
Willy Walker:
The Alpha Trap, not the Alphaholics Anonymous. The Alpha Trap.
Steve Hills:
Partly because people didn't want to be seen as an alcoholic, so we changed that. But it's a great question, I think. And it actually sort of ties in a little bit to some of the things I touch on in the book, in that Kay Graham was one of the most humble people I've ever met. And so here is a woman who was the first woman in the Fortune 500, the first CEO. There's a great picture of 499 male CEOs and Katharine Graham. She was a leader of the first order. She was thrown into that because of her husband's suicide. She was remarkable in that she had the courage of the Pentagon Papers. If you've seen the movie The Post, it really does a good job of sort of showing exactly how courageous she was to be able to take on the government at the highest levels that were threatening her with a felony charge just the month The Washington Post was going public.
Despite that incredible achievement, and all that she'd done, my first dinner at The Post was when I was a summer intern. They sat me next to Katharine Graham. And she spent the entire dinner saying, tell me about what we should do about this, what we should do about that. And you, oh God, I wish I had gone to business school. She was genuinely questioning me, asking me for my advice as a summer intern from business school. And that was her nature. She would just lead with her questions, with her vulnerability, which is very uncharacteristic of men. She would lead with that and ask people questions. She brought on her board; she brought Warren Buffett on. A lot of people said, oh, he's a shark. You know, he's going to try to take over companies. You don't want him. She said, I think he's just really smart. She had no fear of anybody else, despite, in some ways, seeming like she didn't have confidence. What it really was, was a great deal of confidence to be able to be vulnerable.
And so she assembled a remarkable team of leaders, including Warren Buffett on the board. And we had the blue-chip board for many years. She was just truly remarkable. And she built an extraordinary company.
Jeff Bezos, I only worked for two years. And he was enigmatic. And I really enjoyed his company. But his leadership style was much different. Now, he said, look, when it comes to digital technology, that's something I know.
The rest of the business, you know better than I do. I'm going to let the management team run it. But when it comes to the way you're going to shape your product, your digital products, I want to be involved in the pixel. He was very specific, and he had a very strategic view on this. He said, I want to know where I can add value. And I'm going to come in where I can add value.
And that's what I'm going to focus on. The other things, I can't add value. You just do what you're going to do.
In their own ways, each of them knew what their strength was. And each of them had sort of a superpower. And they each led according to that.
Willy Walker:
One of the things I've heard you talk about, Steve, is the need and desire to transform The Washington Post from either being a newspaper company or a media company into a technology company. And I think that in today's world, many of us who are not in the technology sector feel that AI is sort of forcing on us a similar type of change management that was forced on you in The Post back when Bezos brought you. If you can look back at that time period and what the pressures were on you and the transformation that The Post had to go through to go from being a, let's call it, a media company into a technology company. What words of advice would you give leaders as we face this both opportunity but at the same time challenge?
Steve Hills:
It's tough. I hope for everyone else that you don't have the kind of challenge we have at The Washington Post. Because without revealing exact specifics of economics, you basically had a print subscriber who'd be worth $300, $400, $500 per subscriber per year. And you had a world in which they could become a digital user. And at that point, all digital content was free. You're going from this contribution. And someone says, well, I'm going to convert from a print subscriber to a digital subscriber. We weren't paid at that point. I'm going to go from getting $300 or $400 or $500 a year from this person economically to getting a zero. And yet you had to embrace that. We had to embrace it. Because you can't just sit on the sidelines and say, we're going to pretend this isn't happening. We're going to put our fingers in our ears and hum. You have to say, how can I succeed on the terms that are being dictated?
You may not like the terms. But I think, as we have an HR director used to say, reality is an acquired taste. And so the reality of what was happening was pretty brutal. And a lot of people wanted to either put their head in the sand and say, “This is not happening,” or they wanted to give up. But you have no choice. What we had to do was say, OK, let's look at what a world looks like in an all-digital environment and recognize that there are dramatic changes.
And from a strategic point of view, what does that mean? We had to reduce our cost structure. Our cost structure was just untenable in that new world.
But we had to, at the same time, build and invest a great deal in our digital capabilities. You have to have a very rigorous strategy that says, at the same time, we're going to cut; in many cases, when a business model is threatened, you have to cut your costs. At the same time, we have to build up. And we have to maintain our core capabilities and strengths, for instance, our news gathering. How you do all of those at the same time was hard. I did not have this many gray hairs when I started that process.
Willy Walker:
Bear with me as I double-click on this, because I think it is so analogous to what is going on in the world today. Back then, the newsroom and the reporters were The Post. It's what The Post had defined itself on. There were movies made about it. You had editors who had the fortitude and backbone to be able to take down a presidential administration. And that's where the stars were. That's where the power was inside of The Post.
And now, all of a sudden, you're sitting there saying, hold it. For us to be able to transform this enterprise and be able to compete long term, the power of this platform needs to be equally vested in technologists and technology as it is in writers and journalism. How did you approach that cultural shift inside of The Post?
Because there is not a company today, I don't care whether you're in the mortgage business, whether you're in the pharmaceutical business, there's not a company today that is not sitting there looking at resource acquisition, where the technology group is saying for us to go get an engineer to apply this AI is going to cost X, and someone else is saying, well, to get that new salesperson, it's going to be that. What did you see, and what can you offer as advice to people who are trying to make that cultural transformation today in this world, where it's not just The Washington Post and media in a very small space, but across almost every single industry?
Steve Hills:
That's such a great question. I think a couple of things. One is you have to decide what your core strength is as a company. And so the news gathering function was our core strength. What you can't do is—people get threatened. And sometimes people in the newsroom, we were lucky enough to have Marty Baron, we brought on Marty as our editor from Spotlight fame in the globe, just one of the best editors of all time, maybe the best.
And so we're lucky to have somebody with that kind of strategic mindset. But part of the issue is newsrooms; they can feel threatened because they were the only dog. They were sort of like, we are it. And now you're saying to these other people, we have very limited resources because we're being attacked. How can you spend a quarter of a million dollars on a technologist? When that means that could be two reporters that we could be covering. You have to be very careful in your communication that you're not devaluing the core strength because that is your core strength. But we said exactly as you said, we went from saying we're a news organization to saying we are a news and an engineering organization. We called it editors and engineers. And we had our chief engineer, our head of our engineering department, which we formally called IT, of course, but then we realized, no, you have to have people who are genuine.
Willy Walker:
You're owned by Jeff Bezos. There was a lot of rebranding on the technology front.
Steve Hills:
Yes, but even before Jeff, we had to realize that this is where we're going. Jeff clearly brought that to a new level. But we had to say your parallels were equal. We're two sides of the same coin because you have that great journalism. It's not going to get out to people unless you have great digital products, unless the consumer is able to interact with your product seamlessly and be able to find the information. You have to have great engineers to be able to create a great digital product. But of course, the foundation of that product is still the news. You have to think strategically, how do you invest in this new capability? And how do you not have the people who you've relied on for so long feel like it's no longer their company? And that's a very difficult thing to do.
Willy Walker:
One of the things that I know you talked a lot about was putting the customer first. And it's easily said; it's challenging to do that. And particularly at a legacy company like The Washington Post that had such a strong brand that there was a lot of, if you will, pull to the brand.
One of the other things that I heard you say, Steve, that I thought was so interesting was that the newspaper industry came from classifieds and then added the content on top of the classified ads, so that when classifieds went, the underpinnings of the economic model went away. And it made me think, and you tell me if I'm right on this or wrong on this. But I was sort of like, the undermining of the newspaper business is actually more Craigslist than it is Facebook.
Steve Hills:
Well, it's a little bit of both. But you're absolutely right that the underpinning, the history of newspapers, is often people, particularly in the newsroom would say, we had a great newsroom and that led us to build this great business. It's not really quite true.
In fact, people think The Star was a better newspaper than The Post. But The Star went out of business because The Post had a lead in classified advertising. We had a printing and distribution monopoly. That allowed us to make a ton of profit from classified ads. Help, wanted, real estate, cars, et cetera. For young people watching, they're like, what are those?
Willy Walker:
Yeah, right. Exactly. And next, you're going to talk about the Yellow Pages, and they're going to be laying out right now. What are you talking about?
Steve Hills:
Hey, grandpa, come on. We had this great monopoly. I mean, of course, technically I can call it a monopoly now because in those days they couldn't get us for that.
In those days, we didn't call it that. Very strong business, we called it, with a very good moat. And that's why Buffett got into the business. Then that allowed us to increase the resources spent on the newsroom and become the kind of newsroom that would be able to do the things you've talked about. That was really important because then when it got stripped away, it got stripped away from Monster.com, from Cars.com. We ate our own lunch because other people were eating our lunch. Apartments.com. Again, I was on a classified ventures board. We created those products because we had to.
But from a newspaper point of view, all of that, including Craigslist, all of that took away an enormous amount of revenue. And then the problem with Facebook was, and is, from a digital advertising point of view, we're spending a ton of money to generate content. Facebook's spending is zero because you and I generate the content. And then we had to compete against that. It did change. It fundamentally changed the economic model.
Willy Walker:
Then talk about putting the customer first because the customer came to you because of the classifieds. Classifieds have now gone. You're trying to have a customer first business, but the customer necessarily doesn't exactly want what you're selling.
Steve Hills:
Yeah. What happened was that we had two customers. And one of the reasons I love the media business is you have two sets of customers. You have the advertiser, and you have the consumer, the reader. And so that makes it very complicated. Then you have print and digital. You have lots of different complicating factors of how you try to develop this product. What happened from a customer point of view was, from the advertising customers, we lost a huge amount of them in the classified interchange and classified.
Our primary customer, we used to be 90% advertising when I came to The Post. Then that went down and down and down. Then we always had the reader as the customer. And so the reader became a more important customer to us. However, the problem is there's so much more competition. How many daily newspapers do you have in Washington? The answer: one. That was easy. But then how many news sources do you have covering Washington that you can now read with the advent of the digital world? The answer is a thousand.
Putting the customer first, we had to say our customers on the print side have few options, except they don't want the classifieds anymore. And now, on the digital side, you have a substitute for the print. Putting the customer first says we have to recognize that customers, one of the reasons we had to keep our costs so low is saying these customers are going to be able to have lots of choices.
We can no longer say we're the monopoly. We had to then think about how to create that digital product that the customers are going to view as on par with some of the other digital products. And sometimes it's easy to look down your nose and say, well, that's no good. Facebook, these Huffington Posts, that's garbage. They're just rewriting stuff. But consumers have never wanted to pay for quality news in significant enough quantities to be able to pay for our ambitions of our newsroom. We had to sort of figure that out and how to try to make all that work.
Willy Walker:
Yeah, in a speech you gave back in 2014, I heard you talk about interestingness. Like we're going to make, we got to focus on making The Post, what we're putting out, and interestingness. And I was sitting there sort of like, that's different from just reporting. And it's different from analytics. And it's also, in some instances, different from potentially the truth. And in that speech, you talked about the need for truth and how our world has evolved over the last 12 years as it relates to the need for truth is something I want to get you to comment on in a second. But let's stay on this interestingness comment, because I found that to be, something would tell me that you sat around before that speech and debated whether you would use that term as something that The Post was striving to achieve.
Steve Hills:
Yeah. Yeah. It's a great question because there's some tricky parts to it. And Bezos would talk a lot about this. The simple idea is in order to have an impact from a news point of view, you have to be read. In the online world, you have to be clicked on. The issue is if you have a headline, that's an accurate headline, the headline says, budget impasse due to Democrats talking about the filibuster. You may get nobody clicking on it. People may say, not enough people are interested in that. If you say something that's a little bit more inflammatory, the same exact story, you don't change the story, but you get clicked on. The danger is, what does that create in the ecosystem broadly, which is these wildly inflammatory headlines? And I know I wrote an op-ed for USA Today actually, and they changed the headline to make it more clickable.
And online was more nuanced. There was one; this happens a lot. The issue is we wouldn't change the story itself. We just say, is it a good story? But for the headlines, we did lots of A-B testing. But the issue that's tough about that is what it's led to, if it's led to, there were always, there were the listicles—that was for a while, the seven ideas you can't do without—that became a big thing.
But then it's now become, I think, part of the problem, like social media has been wildly bad for our democracy, because I think that it's tended to lead people to extremes. Because if I see something that's nuanced, if I see something that says, Republicans are burning this place to the ground. Democrats are all socialists who want to take your money, it's unfortunately more likely to get clicked on. That's a battle between the quality news and the clicking that, honestly, is part of the reason I left the media business. I don't know how to put that genie back in the bottle. And it was very frustrating to me to see that. I can tell you, at The Post, we would not change stories to try to make it more clickable, but we would look at headlines saying we need to click on this.
Willy Walker:
You also talked about reducing the cognitive overhead. And when I read cognitive overhead, that just means you're dumbing things down. And is that fair? I think about Bill Bradley, and I think about him hearing about reducing cognitive overhead at The Washington Post and rolling over in his grave at Oak Hill Cemetery in Washington, DC.
Steve Hills:
I'll answer that. It's not about, in that case, it was really saying you want to make it as easy as possible to get in. The question, that wasn't about the content. It wasn't making the content less complex. The idea was making the user experience less onerous. You wouldn't say, I got to come in and look at the site and like, where do I go? And I got nine things that are pointing me in different directions. That's the cognitive load we're trying to reduce. Not sort of saying, hey, to dumb it down for you, government, bad, we're not going there.
Willy Walker:
And so I want to talk a little bit more about this, and then I want to shift to The Alpha Trap. But as I think about the time that Bezos stepped in and bought The Post, there were a couple things that I sort of thought back to, that I'd love your thoughts on as it relates to, I guess, number one would be this: would it have been different if The Post had been acquired by Amazon versus acquired by Bezos as an individual?
Steve Hills:
Oh, 100%. Yeah. Because, look, I spent a lot of time with Jeff and probably spent, I don't know, 80 hours with the guy and within meetings and group meetings and with a relatively small group, a small number of us. I got to know him pretty well, as well as you can get to know someone like that. He is inscrutable.
I can sort of say that I don't know exactly what his motivations are. My belief at the time was that he wanted to do this because he wanted The Washington Post to be The Washington Post, to be the guard dog for Washington, that we need that from a democracy point of view. My hope is that's still the case.
But that was what it was.
And Amazon would be just saying, in order to be good corporate stewards, how does this maximize the value of Amazon over the long term? And that would have been a very, very bad thing. And the Graham family would not have sold to Amazon. They sold to Jeff because Don, Katharine, the lineage from Katharine Graham on down, would care deeply about making sure that The Washington Post was in the hands of a steward who would care for it for all the reasons that we all love The Washington Post.
Willy Walker:
If you think back to when he acquired The Post, how different would the history of The Post over the last decade be if Hillary Clinton had been elected president in 2016 versus Donald Trump?
Steve Hills:
Wow. That's a podcast on its own. What I would say is that from my vantage point, I think that Donald Trump is a symptom and is one of the worst views, a sort of metastasized version of a symptom.
But I think he's a symptom of a lot of what's happening throughout the world of people being, feeling left behind by globalism, feeling that they had no choice and feeling like, okay, here's somebody who's saying, I'm essentially going to burn the system to the ground. I'm going to just upend all of the norms we've had. And people are saying, I'll take a redeal. I'll take anything over what we got.
Had Hillary won, I think a lot of things that have happened that, from my vantage point, are bad, anti-democratic, leaning towards fascist, things that I think are problematic, I think wouldn't have happened then. I'm not sure they wouldn't have happened later. I think when you look at what's happened throughout the world, there is a move to people just saying, I don't like the results of things. I want to make things go back the way they were. It's easy to blame the scapegoats, the immigrants, all the people who are doing this to you. And I'm not sure. I'm not sure. It's an interesting history to try to imagine what that would have looked like. But I think we might've just had to have this day of reckoning no matter what. And the reckoning will also be very important: what happens in November in these midterms, very important what happens in 2028. And those chapters have yet to be written.
Willy Walker:
When, if you roll the clock back to 2016 and where the New York Times, The Washington Post and the Wall Street Journal stood as it relates to distribution, online views, what have you, it was really sort of a three-horse race. And the Times has grown exponentially larger and faster than the Journal and The Post. And the Journal has, is, is firmly in second place. And The Post has fallen down to third.
As you look back on what The Post did versus what the Times or the Journal have done, what's the thing that The New York Times most specifically, because they're the one that has grown the most, what did they get right over the last decade that has positioned them so well?
Steve Hills:
Yeah. The first thing is, you have to set the Journal aside because the Journal is sort of its own kind, sui generis. It's sort of like the fact of it being a must-read for a certain audience, but also somewhat limited because of the business audience. I think the Journal is independent.
The Post, people in the newsroom always wanted to compete with the Times because journalistically, we could sort of hold our own. But the truth is by virtue, the Times has so many natural advantages. They're in New York City, they're in the media capital of the world. It's five times larger than the Washington market. And for the longest time, the primary profits were driven by the local market. You have studios, you have banks, you have high fashion. You have all the ad agencies centered there. It has massive collective advantages from a publishing point of view. And it isn't very smart. And also this very well-run period, but they recognized through crosswords when they were looking and doing their analytics that crosswords were key to their digital subscriptions. And by seeing that, and by seeing how important it was, because crosswords cost you this and give you this in economics. The newsroom costs you this and gives you a lot of economics. They said, what could we do more like crosswords?
I think getting into games, if it wasn't for what the Times has done with games, I think we'd be telling a very, very different story. They've been brilliant. And then they've also done the cooking, the expansions, but they're also, because there has always been about New York City culture that leads you naturally into some of the things they've gotten into adjacency. I think strategically they had a far better hand to play. And they played it beautifully.
Willy Walker:
You're talking about the crossword puzzle. I got to tell this anecdote, and I had no, this did not even come into my mind as I was getting prepped for this, but because you went to the crossword puzzle, I got to share one quick anecdote with you, which I think you will appreciate.
Second year at HBS, and I've got an offer from McKinsey, and I'm trying to figure out whether, what office I might want to go work for McKinsey. I go to San Francisco, I'm in the Transamerica building, I'm up top. I went to meet some people who were second-years in my first year to talk about what it's like to be in the McKinsey San Francisco office. And I get in the elevator, and I'm going down in the Transamerica building, and this McKinsey partner steps in. And he says to me, how'd it go, thinking that I was interviewing him. I go, oh no, I've got an offer. I'm just trying to figure out whether I want to come to your office.
And he goes, I got a question for you. And the elevator's going down, Steve, and it's just the two of us in the elevator. And he goes, do you get the Sunday New York Times? I said, I do. He goes, what do you read first? I go, the front page. He goes, what do you read second? I said, the business section. He goes, what do you read third? I go, the week in review. He goes, what do you read fourth? I go, the sports page. He goes, do you ever get to the crossword puzzle? And I looked at him, and I go, no, I hate crossword puzzles. I don't like crossword puzzles. That's not me. And he looks at me, and he goes, you look like someone who wants to do something. At McKinsey, we solve crossword puzzles every single day, and that's what we do for a living. Go do something with your life. And literally, we get to the bottom. The doors open up of the elevator. He walks out. And I literally called McKinsey and Bain and said, thank you very much. I'm not going into consulting.
And obviously, the beauty of the story is he looked at me as a crossword puzzle and solved the crossword puzzle before the elevator had even gotten to the bottom floor. And I, to this day, thank him for sending me out to go “do something,” rather than trying to be a consultant. Anyway, you mentioned the New York Times crossword puzzle, so I had to bring that one up. I don't tell that story very often.
A couple of other things before we move off of it. You talk a bunch about Bezos-isms. And given Jeff's role in our world and being one of the richest men in the world and what he's done both with Amazon and is now doing with Blue Origin, you got a couple or one or two Bezos-isms that have sort of stuck with you that those of us who lead businesses or lead teams ought to keep in mind that you got some insight in those 80-plus hours of being in media.
Steve Hills:
Yeah. One of them was fascinating, which is that he came early to a senior manager meeting. We had a problem we've been working on for years. And we said, hey, it's a really complicated problem. What do you think? Laid it out for him. And he said, maybe it's just too hard. We're like, this is the genius? Like, that's your guy? And he said, maybe he's just working on something else. And he said, here, the problem is that people tend to spend a lot of time, we love to solve problems. But the question is, if you spent the same amount of time you've been trying to solve this problem, trying to develop opportunities, could you have just done a lot better? Because after a point, when you have your best and brightest really struggling with something, instead of saying, we're trying to fix that problem, maybe you go to build other opportunities. Find out, and he used to talk about, find out what's working and pour gasoline on it. And he meant in a good way, not burn it to the ground. Let's look at what's working and build on that. Instead of trying, because we are so drawn to trying to solve these thorny problems, that often we can then spend too much time and collective organizational energy solving problems rather than building new things. I thought that was really an interesting way of looking at the world.
Willy Walker:
Yeah, that's great. Final one on this, and then I want to shift. In a Q&A that you did a number of years ago at the INMA conference, you were asked about the truth. And I have to put out that this is 2014 or 2015, so over a decade ago. But the quote that I picked up from that was, someone asked you whether the truth matters. And you said, “If people don't care if it's true, we're in big trouble.”
Given the world we live in today, Steve, and the number of people who look at stuff online and have absolutely no regard for its veracity or whether it's true or not. Are we in big trouble?
Steve Hills:
I think we are. I mean, I think when we started talking about these Orwellian phrases, alternative facts is one of the scariest things I've ever thought.
Willy Walker:
Kellyanne Conway.
Steve Hills:
Yeah. I studied philosophy. You sort of think there are things that are true and things that are not true. And there are things that are in between. But the idea of the falsehoods that are being conveyed about, we were never a racist country. It's like we bought and sold people based on race.
The election: Trump won the 2020 election. There was no global, there was no climate change, man-made climate change. These are just things that are factual answers that are presented every single day. And this is hard for journalists because journalists do say the disproven, the discredited; all the major papers—the Times, Journal, and Post will say, Trump says this, but it's discredited. But he's just, it's that repetitive; it's the Goebbels line. If you repeat something over and over a lie long enough that people will start to believe it's the truth. I think that there's a lot of that going on, that people are discovering that because you can select your own media outlets, you can say some things and enough people will be out there amplifying what you say that is demonstrably not true. I think that is a real problem for our democracy.
Willy Walker:
Any solutions to it?
Steve Hills:
I don't know. I've thought, I actually think, I have a hopeful view of AI. You and I were at the Sun Valley conference where they're talking about this question.
And it's a woman talking about: Is AI going to just destroy the world? I'm sort of a bit of a technology optimist in that I think that where AI could potentially be a salt is right now, if you go to AI, now I'm just talking about the major AI, let's talk about Claude and ChatGPT, if you go into them, and Gemini, and if you say who won the 2020 election will be Joe Biden. It's possible that, instead of the social media feed telling you what you want to hear, if you believe X, it'll tell you X.
Instead of that algorithm working, if people start using AI, instead, maybe we'll have more access to the truth; maybe more people will see the truth. Now, there'll be other people who decide to create an AI, put their thumb on the scale; there'll be bad actors. But maybe that's a way out. A hope for a way out.
Willy Walker:
Yeah, certainly can hope for some of the bigger brands to hold firm and be able to set the standard, which I think that if I if I think back to your comments 12 years ago, you very much believe that the big brands would continue to aggregate importance, because they would be the standard bearers that they would be the ones that people could rely on for for truth. And clearly, I think that part of the growth in The New York Times does come from that. I mean, when I want to go and fact-check something, I still place a tremendous amount of faith that The Times is upholding a mandate of some degree to—
Steve Hills:
The paper of record.
Willy Walker:
Exactly. You got it. And so I do think that that continues to hopefully continue to grow.
Let's shift for a second to The Alpha Trap. You've been around alpha. By the way, if I say alpha males, the book is predominantly about men, but there are clearly alpha females as well. And so I don't want to just go to the male side of the equation. But alpha men and women since probably high school, but very clearly being at Yale and being at Harvard Business School, you've been around a lot of these people for a very long period of time. Why did you decide to focus on this topic? And what was the most surprising thing you have learned in interviewing hundreds of people that you defined as alpha male or alpha female?
Steve Hills:
Yeah. I interviewed these people based on a thought of the alpha, including CEOs, professional athletes, people who've been in high levels of government, founders, and interestingly, what I found is gets a little bit to the male female thing.
There is a male tendency of alpha male behavior that's over two million years since the Pleistocene. There have been certain things that men predominantly have done to get status and resources. And that's the thing that the society has changed. But relative to that two million year evolution, societal changes are very, very recent.
The thing that surprised me is all these things are about tendencies. Also, they're not about absolutes. You can say, well, I know a person who's different from that, of course. But the vast majority of the men in this have effectively outsourced their friendships. The development of that and their social life to their to to a spouse or significant other and like and talk to this one case of a guy who says my wife tells me who we're having dinner with. I just talked to someone who interviewed this woman who said, and they both have big jobs. But she said, well, I just told my husband, remind him to call his friend because it's his birthday. I remind him of this so that and what I found on the flip side that sort of is the dovetail to that is women alphas.
There are women who are CEOs of major companies. Two things. One is they still were telling their husband who we're having dinner with, who is to remind someone to call because of their birthdays and also women or even these people who are extremely busy. They have a network of women, friends, and I think they can tend to get tendencies, not absolutes, if they're vulnerable with each other. They support each other to create a web of relationships, whereas men, we tend to not male loneliness is at an epidemic level. And I think a lot of the reason I got into this was I'm fascinated by my own perspective of my own life and how I'm learning about this, how much I've learned from my wife about connection, about things like that.
I'll give an example. If you ask why I did this, I spent my life and I realized I spent so much of my life trying to figure out how to be admired. And I've been trying to be successful in this. I compete in that. I compete in everything.
Very competitive guy. Willy, I think you know a little bit about that yourself. I love to compete for things. I want to win. And what I realized was I spent so much time wanting to be admired. And I thought back to my father.
As you get older, you think about these things. He was such an influential person. He went to Yale undergrad. He went to Harvard Medical School, the Mayo Clinic. He was chief of staff of a local hospital. He was a competitor, played tennis, played bridge, and poker. And I learned about how admired he was.
When I saw him once in his lab coat in the office, it was like, oh that he was just so revered. And yet at his funeral, I was struck that nobody really knew him. Nobody really told the stories. And as his son, I knew him as a father. We'd watch football games together. We'd do things together. He was uncomfortable in the sense that he was so comfortable in his work world, but just uncomfortable in the family world. The rules weren't clear and he didn't quite know how to be vulnerable in those things.
It struck me that I wanted to study this and figure out how are people approaching this question of, if you have a life built on being admired, what do you do in the next parts to try to maybe build other parts that are richer and can maybe lead to longer, more sustaining fulfillment?
Willy Walker:
The title of Alpha Trap, as you were doing these interviews, do you think any of your subjects had an aha moment that they sort of were caught in a trap?
Steve Hills:
Yeah, I think so . I had a great conversation with Mats Wilander, seven-time Grand Slam winner. And one, I think the first branch opening of 16.
Willy Walker:
Sun Valley resident.
Steve Hills:
A Sun Valley resident. And he and I talked, and he said, " Hey, this is really helpful because I need friends, and I'm not used to initiating it. I don't have, he said, I sort of in tennis, I knew what I was doing. And I think this is such an analogy for so many of us, like in your work world, you're on top, but you know what's going on. You know how to pull the levers; you just feel totally confident, and we feel this way. But it was fascinating when he said this; he said, like, even a guy with that level of success, just sort of saying, when it comes to friendships, that's a whole different deal. I need to initiate more. And I think we talked about that. And I found that with a lot of people in the interviews and talking it through, they were like some of these things, I recognize these patterns you're talking about in myself.
Willy Walker:
And what about, I mean, in your description of the personal life versus the professional life, how hard was it for you to get your subjects to open up to you? Because these are typically people who have succeeded in life. They want everyone to think that to some degree, they may or may not be perfect or as close to perfect as they want to be.
How open and revealing were they as it relates to either a struggle they had or a work to their overall persona that they were willing to share with you and talk about?
Steve Hills:
That's a great question because you always have to think about the reliability of the narrator. What I found out that was really interesting is these people for the most part were very revealing. Now I'd say there were 10%, 20% of people who were just, they were telling the story like they were telling it to the biographer saying this would make me look good.
I kind of quickly realized for some people, I just wasn't going to go there. And maybe they didn't have the self-knowledge or they just didn't trust me, whatever it was. One thing I did that was interesting. I said to people, you can correct; I want you to say this. And if it's something you said, but they aren't the words that you would pick, even if you said it as a reporter, I'd say, what you said, you said it's on the record. But here I said, no, no, you, you get to look at everything.
The fascinating thing was, nobody was only with one, basically maybe one or two people, but out of over a hundred people, very few people came back and said, I want to change this. Someone changed it. They said, well, that didn't mean that it said this, but very few people came back and said, well, that's too vulnerable.
A couple of people said, very fairly said, this is so vulnerable. I want you to disguise my name. And I did. I probably disguised 10%, 20% of the people, but in many cases, I could completely understand why they wanted it disguised. But for the most part, people were actually surprisingly open about it. I think they viewed it as sort of a cathartic experience to talk about it.
Willy Walker:
Was there any difference? I often, when people come and ask me for sort of management advice, leadership advice, what have you, and they start by saying, "You run this big company and my company is just this small thing. I always kind of stop them and say, the only difference between what you do every day and what I do every day is a couple of zeros.
The issues are all exactly the same: the same HR issues, the same accounting; everything is sort of the same. It's just a matter of scale. As you talk to the various leaders, did it matter either the scale of what they had done or accomplished or the industry that they were in? You talked to people who'd been in government. You talked to people who'd been professional athletes. You talked to people who'd been CEOs. Was there any differentiator by either industry practice or by scale that you could differentiate between the large cohort that you interviewed?
Steve Hills:
I'd say no. Your experience is exactly mine. I started my own small business out of a college of $2,000 I'd saved as a bartender. I started a newspaper I ran for a year and a half in California. I came to The Washington Post. I was like, this is the same. It's the same thing, just a lot of zeros in that case. But that's it. And so I found the same thing true here.
In a lot of ways, what the whole thesis that I had going on has been really proven, for the most part, is that people are wiring from the Pleistocene era, like our wiring to get status and resources. And the idea was originally to get it from mate selection because we lived to be 35. We didn't have the second half to worry about our lives. That was what we did. And those of us who did that successfully propagated the genes. And that's why a lot of us have this wiring.
That wiring is the wiring. And it doesn't matter if you're in a big company, a small company, if you're in a public company, if you're a government employee, if you're an athlete; we're all—those of us who have that wiring, we are competing, and we're competing to be, to get status and resources. That's our fundamental drive. How it's applied is different. But basically I think the drive is the same. And that's been my experience through the interviews.
Willy Walker:
Your cohort was largely either at the end of their professional career or beyond their professional career, reflecting back on their professional career. You got people's perspective, if you will, as it relates to that transition period.
When we were together in Sun Valley, Arthur Brooks spoke, and Arthur's book From Strength to Strength, I think is one of the most incredible books on sort of like transition from pre-50 to post-50, if you will. And the things that we need to have in our lives to live long and engaging lives. In doing the interviews, did you pick anything up from those who have “successfully,” and success is defined by you, there's no definition of that, successfully have transitioned from an alpha career and you wouldn't have been speaking to them unless they had had success.
They were successful in their career and they have figured out how to transition. And then those potentially that didn't and things that you would point out that they just kind of haven't gotten the memo on.
Steve Hills:
Yeah. So a couple of things. Great question. So one of them is that I have some actual examples of people. One guy is 83 years old and, he said, look, I was a 10 out of 10 alpha. Here are the ways I screwed up. I did all these things. And he's extremely meticulous, methodical about how he's gone after this. What it really is, is saying the way people have solved for this, because it's never solved. It's always a work in progress. There's no destination like, Oh, I just figured it out. And then I went to this point and now I'm happy. The idea is it's all work in progress, but like a strategy in business, it's people who say, I have this thing called the life priorities wheel.
People can go to TheAlphaTrap.com and you can actually take this wheel. It's all there's no cost for any of this. I set up some tools to be able to do this. You can test to see how much of an alpha you are. And what the wheel does is it basically says of your priorities as work and wealth is one slice of this wheel. Or do you want to focus on your spouse, significant other, that relationship? Or is it your family? Or is it contributions or giving back? Or is it inner life, sort of inner peace? Is that something you want? Or is it healthy?
The idea is to select what you want, what you want to focus on. And then there are lots of tools for focusing on. And there are examples of people who've done that. To your point, there's no right answer. The only right answer, because in fact, some people would say, I'm working just as hard as ever. I'm going to work at my job, and I'm going to do it till I'm 100 and they're fine with it. And that's okay for them.
But the question underneath it to your question, again, the memo is what's troubling. And there are some people who you say, well, they said, I wish I had a better relationship with my kids, but what are you going to do? Well, what you're going to do is focus on that and do some action, just like a strategy in business. You say, what are your resources, your time and attention? You're going to apply to that. If you say that's a problem, but I'm not going to do anything about it. Well, that's the problem. And there are some of those cases, but there are a lot more other cases where people solved for the problems they were trying to get more of. But that we're all a work in progress.
Willy Walker:
That reminds me of a scene from the television series, the lioness, where the woman who's the CIA agent and her husband, who's a surgeon, their daughters in a car crash. And she also, as they're putting her back together, they find out that she's pregnant, and she's 14 years old. And they're having this conversation and they're like, we need to change something. And it's like, they're both sitting there sort of like we know we need to change something, but neither of us is willing to give it up to actually do it.
Steve Hills:
So the first step is to, that's why I started calling it Alphaholics Anonymous was the idea that the first step is to say you have a problem. That's kind of the idea of it. But the AlphaTrap is the same idea, which is to say, the first step is to say, I, my current path is going to lead me to success by a lot of measures, but it's not going to give me what I actually want. And so what do I actually want?
Now, once you figure it out, and I have lots of examples of this in my own life, I figured out what I want. I'm kind of on a path I feel very good about, but on a day-to-day basis, I go, I just screwed that up, just in the way I tend to always screw that up. I tend to do the same stuff I tend to do. Just getting the awareness of it is helpful.
Willy Walker:
And when you think about your comment about men and women, you worked for the first woman to be on the Fortune 500 list. You interviewed numerous women who have been very, very successful in their careers and you started your comments here, Steve, talking about the fact that the women CEOs not only are great at being CEOs, but they also can deal with the personal side of things. What can the men listening to this podcast and webcast learn from the way that they balance those two sides of the challenge?
Steve Hills:
I think, and the broad strokes, I think the one thing that women tend to do better, again, tend to do better than men. And Katharine Graham was an example of this as are most of the women I talked to is to not be afraid to lead with vulnerability. I think this is something because of men's competitiveness.
I talk a little, there's a chapter on games we play and the games, and the game that I love, and like poker, my dad watched him play poker and bridge. These are limited information games. And you grow up, watch it.
And the idea is to hide poker face. People think of poker face, like a man sitting there and not you're strong, you don't show anything. And that's the problem.
We're brought up with that. Women through a combination of, I think, biology and socialization are much more comfortable being vulnerable. And I think that that's a lot. It's great. One thing I love, for instance, on a board is when the CEO, you don't want to come in and say, I'm feeling sad and lost, help me. You know, you don't want the CEO to be like that. But it is nice when a CEO says, here's something I have a point of view, I have the beliefs, but I need the board's help on this. I I want to ask you a question. It's good to have that to me.
It's, being vulnerable is something I think generally that I think in terms of friendships and in terms of just creating more balance in your life. I think that's something men could learn from women.
Willy Walker:
So interesting. I wasn't planning on bringing this up either, but today, because I know you so well, today is my grandmother's birthday. Was she still alive? I think my grandmother would be 110 years old today. And she was a very good friend of Kay Graham's. And my grandmother was also hard of hearing. And one of my friends, when my grandmother died back in the early 2000s, at her funeral, he said, just imagine if Granny Dorcas was her name, just imagine if Granny Dorcas's hearing was better. And she, like, how incredible that would have been for her. And I turned to this friend of mine, and I said to him, her vulnerability, her disability was her gift. I said, if she hadn't been hard of hearing, she wouldn't have woken up every morning and read The Washington Post and the New York Times cover to cover, because that was her defense from not being able to hear what you were saying, because if she knew the news better than you knew the news, she always had something that she could bring up with you to make it that she kind of knew enough about it in depth from reading The Post or the New York Times that if she missed some point you made in your comments to her, she wouldn't lose the narrative because she knew enough about it. And therefore, when she sat down with you, she wanted to start a conversation. She wanted to ask you questions.
And I sort of said if she'd just been another elderly woman in Washington, she probably would have stuck to her friends, done her own deal and not been as inquisitive about you and all of my friends as she was. And it was such an interesting flip for my friend who was sort of like, oh, it was such a shame that she was hard of hearing. And then I was like, no, that was her superpower.
And so to your point about women embracing vulnerability and talking about those types of things, I do find that to be really interesting. And on my grandmother's birthday, I just thought I'd bring that up. And particularly that she and Kay were such good friends.
Steve Hills:
Yeah. We also get to another point there, which is important, which is this idea that inquiry, like how many times as men, when we want to be admired, do we lead with what we're doing and what we've done? Hey, I used to be the president of The Washington Post. I'm sort of bored. I mean, tell you this versus how often I think about my wife in this, where she'll talk, what are you like? What's important to you? What's going on in your life? And I try to learn from that because I think that's another part of it. When you spend your time trying to know people and be known as opposed to being admired, I think it's a whole different orientation.
Willy Walker:
It's really interesting. Burning Man starts at the end of this week. And I went to Burning Man last year for the one time, and I'm not going back this year. But one of the things that I found so refreshing there is that people don't introduce themselves, hi, I'm Willy, and I'm from here, and I do this. Or hi, I'm Steve, and I went to Yale and went to Harvard Business School. It's real.
It's what's going on in the moment and who you are, and not what your bio is.
Steve Hills:
And I talk about this in the book. There's a thing, the Hoffman Project. And one of the guys who went through it, Frank Williams, the CEO, we both know, a really talented guy. And he talks about one of the aspects. And one of the aspects of this is that he actually, you go to the Hoffman Project, you're not allowed to say what you do, because then it gets you away from this idea of your image of yourself strictly by your accomplishments, which is part of the powerful process.
Willy Walker:
I've done Hoffman. It's really interesting as the week evolves, you sort of make up your own narrative about somebody. They talk about their life, and you're putting together this puzzle, if you will. But they haven't sort of said, I work at a creative arts agency in L.A. And I am an agent XYZ person. But as the week goes on, you sit there and go, all right, hang on. This person lives in Southern California. They know a lot of people in the entertainment industry. And I don't think that they're an entertainer and you sort of back into it somehow. But you make your own. And then all of a sudden you find out that they either are or aren't. And then all of a sudden they say, no, I'm a farmer in Des Moines, Iowa. And you're sort of like, oh, I missed that one.
Steve Hills:
Yeah. And we may be because of our alpha nature, subtly trying to rank them, rank our status relative to them. That's something.
Willy Walker:
Oh, 100% And who am I going to want to follow up with after here? Who has an interesting life that I might want to go meet with? No doubt. Steve, fascinating. So much fun. I obviously get the privilege of being able to have conversations like this with you on a frequent basis. But for you to come on the Walker Webcast and talk at this time as it relates to technological implementation into business writ large and then talk about your book has been a real treat.
Thank you for taking the time.
Steve Hills:
Well, it's been a pleasure. Thank you for having me.
Willy Walker:
No, it's great. Thank you for joining us this week. We will be back next week and appreciate you tuning in.
Thanks again, Steve.
Steve Hills:
Okay, welcome.
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