Leadership in Context

Our need for simplicity belies the complex reality of leadership

A month after he purchased Twitter last fall, Elon Musk posted a photo captioned “My bedside table.” 

Musk’s bedside menagerie included: four open cans of Diet-Coke; bound copies of the Declaration of Independence and the Constitution; a “cosplay gun” (according to the New York Post); and what appears to be a replica of George Washington’s flintlock pistol, displayed in a box with an image of Emanuel Leutze’s famous painting of Washington crossing the Delaware. 

Musk is famously adept at Twitter trolling, and I gathered that these symbols — of aggression, freedom, resolve, and caffeine-free artificial sweetening — were meant to be funny, but also to convey something about his leadership values.

“Washington Crossing the Delaware” particularly caught my eye, because it was a centerpiece of one of the most interesting leadership talks I’ve ever seen. The man who delivered that talk was Jeff Eggers, a 20-year military veteran and former Navy SEAL who spent six years in the White House working for presidents Bush and Obama; Eggers was recognized for his role in mediation following the 2014 Afghan presidential electoral crisis. Needless to say, he knows a thing or three about leadership. 

The point that Eggers made in the talk that I saw was that the portrayal of George Washington in that famous painting is both ahistorical and misleading as a leadership lesson. 

When Eggers worked as president Obama’s special assistant for national security affairs, he spent a lot of time in the West Wing lobby, waiting on a nice blue couch, above which hangs a reproduction of “Washington Crossing the Delaware.” 

Emanuel Leutze’s famous depiction of Washington crossing the Delaware. [GraphicaArtis/Getty Images]

Eggers was often sitting there when tour groups came through, so he learned a lot about that painting, including that the Delaware River never froze in that way; the flag depicted hadn’t been created yet; the boat’s going the wrong way; and it’s the wrong kind of boat. 

In a more accurate, and much less heralded painting, Washington isn’t striking a Captain Morgan pose, “because it’s ridiculous,” as Eggers put it. Rather, he’s clutching the wheel of a cannon so as to keep his balance, because that’s what human beings do in a boat at night. And yet, nobody thinks “ridiculous” when they see the famous painting; they think: “confident,” “leader,” “courage.” That is because, Eggers argues, we all subscribe to the myth of leadership in which we exaggerate who leaders are and what they can do.

A more accurate depiction of Washington crossing the Delaware, painted by Mort Künstler.

Eggers and his coauthors — retired general Stanley McChrystal and former Marine Jason Mangone — write in their excellent book, Leaders: Myth and Reality, about a misunderstanding involving another famous leader and his river crossing: 

“History codified Caesar’s ‘The die is cast’ as a declaration of courage and decisiveness.”

But, in fact, Plutarch framed the moment before troops crossed the Rubicon as one of serious doubt, in which Caesar ordered a halt and sought counsel from peers. 

Eggers points out profound paradoxes in how we talk about leadership, like the fact that leadership theory extols the value of humility, and yet narcissists are overrepresented in leadership positions. 

Leaders: Myth and Reality is structured in sections that feature pairs of historical leaders who represent a certain genre (founders, geniuses, zealots, etc.), and who are compared and contrasted in search of lessons. After reading the book, I reached out to Jeff to chat about it. Below is an edited version of our conversation. As usual with my Q&As, this is longer than a typical post. 

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David Epstein: In the “Founders” section of the book you compare Walt Disney and Coco Chanel. One thing that struck me was that they sort of took full advantage of the “great man theory” kind of thinking. Even though they each had a huge support staff, they really worked to have their names singularly associated with all creative production. They were visionaries, but they had a lot of help. It’s almost like they recognized how seductive the idea of everything coming from one brain was, and so they perpetuated that. 

Jeff Eggers: The only issue I would take with that is that I don’t think they were deliberate in engineering in that way. I think they emerged as successful or attractive because of an outlying pathology where they believed that genuinely. It’s not like they understood it academically, it’s just the way their brains were wired. I think that’s much like how Elon Musk operates. It’s more that these kind of outlying psychological profiles are the ones that resonate the most and they sort of generally emerge to that position. 

DE: Got it. So they weren’t explicitly hatching some strategy to capitalize on a human psychological need for singular heroes, but rather they just sort of operated as visionaries very bound to their own vision, and were good enough that others were attracted to them, even if those others didn’t get much credit. That reminds me of the seminal work of sociologist Howard Becker, on what he called “art worlds,” these giant systems of conventions and tools and colleagues that enable creators to do what they do, but that are often downplayed or entirely ignored. 

JE: That point about systemic importance is absolutely part of the sophistication of the book that we struggled with. Because part of what we're saying is: humans are attracted to simplicity. They like to boil things down to sort of binary and simple things, because the world is complex and overwhelming. And so the leaders that we gravitate toward are the ones that appeal to that part of our thinking. And yet, the realities of the human system that gravitates to that leader is anything but simple, right? And so there's a huge tension there. 

That was a big part of what [coauthors] Jay Mangone and Stanley McChrystal brought into the book was that respect for the context. We each had questions that started the book project. My questions all had to do with the “strong man” myth. Jason’s were similar. For example: Why is it that Boss Tweed got elected into office after he was publicly exposed and indicted for fraud and corruption? How does that happen? Stan’s was all about Robert E. Lee: Why is it that the general who was both patently on the wrong side of the war — and lost — gets held up by historians as this great general. How does that happen? 

One of Stan’s other contextual questions was: Why is it that you can take a championship winning head coach out of one system, throw three times as much money at them, drop them into this college or that team, and their record is abysmal? What changed? Well, everything. The context changed.

I don't know if this is what [sociologist Howard] Becker is getting at, but one of the reasons for why I think this theory of a sort of paradox, or attention-based model of leadership in the human species is the right one is that, to the extent we can tell, it emerged about the time our surrounding context underwent a categorical shift in complexity. We went from a hunter-gatherer based system, to a settled agricultural base, city-state system. That was the point at which we went from an acephalous species to a hierarchical one, and we've been conflicted ever since. So I do think that our desire to find sort of the lowest energy state, or simplest way through a complex environment is very much behind these phenomena. I'm not sure if that's the question you were asking, David. 

DE: I don’t even think I asked a clear question; I’m just trying to get you to think out loud with me. And I didn’t mean to suggest too strongly that Disney and Chanel were consciously taking advantage of human psychology. And Becker doesn’t suggest that either. Rather, he suggests that if the creator or performer completely eschews the system of conventions in their field, then basically they won’t make an impact, no matter how creative they are. So at some level they have to understand the system that empowers their work, even if they don’t credit it.

JE: Well, I actually think — not to get political — but I’ve had this conversation with people recently. You know, when you look at people like Marjorie Taylor Greene, I think she’s a classic example of that. She has a voice because she has an outlying pathology, but she’s also smart enough to understand the way she needs to sort of temper, moderate, calibrate that base off of the contextual winds. And that’s where you get the resonance, right? Because if you’re fully outlying, and you don’t have that ability to calibrate, it doesn’t work. You know, Elon Musk would be harder to kind of categorize in that way. But I got into a conversation recently where someone put her in that category and that really struck me, and I think it’s right. 

DE: I think Elon Musk understands memes about as well as anyone on social media. The way that he uses them suggests to me that he understands that sometimes people are just in it “for the lulz,” as the saying goes. It’s like some weird modern version of the Colosseum, and entertainment, and often anti-earnestness trumps all. To me, he seems very clever about that. 

But that issue of how far outlying the psychology of some leaders is gets to another issue, I think. I’ve been reading some of the work of Nobel laureate economist Douglass North, about how the evolution of institutions determined economic growth (or lack thereof) of countries. One of the things he writes about is how even when society is completely turned upside down, like in the French Revolution, the mark of prior institutions remains. Institutions don’t tend to just get thrown out wholesale and remade; there’s some historical memory. And there were two parts in your book, one where you wrote about the U.S. going into Iraq and trying to throw out all the institutional memory — so-called “de-Ba’athification” — just getting rid of everything and everyone that was there. And you write about how that was a problem because it eviscerated some of the institutions that kept stability. And then that idea is in the book again, in the chapter about Robespierre and the French Revolution, where he’s pushing for an overturning of institutions. And it works, but then maybe he goes too far when he tries to create a new national religion, the “Cult of the Supreme Being.” With startling speed he goes from icon of the revolution to beheaded. So that didn’t go so great. 

What am I getting at? You advocate in the book for a new, more complex form of leadership education; I wonder if part of that should be an education on institutions, and how our institutions evolved so that leaders can understand the progression of institutions in a society or organization, and maybe what can and can’t be changed in one fell swoop without crumbling the entire society, or organization. With the U.S. in Iraq, and with Robespierre, maybe there was a bit of a lack of acknowledgment of the fact that change needs to be grounded to some degree in knowledge of existing institutions, even when you’re overturning things. Does that make any sense? 

JE: It does. And that's something I would probably write differently in the book if we wrote it today. I've been thinking about it a lot in the context of the current national mood. I think we take for granted the role institutions play and how dependent we are upon institutional structures and processes to allow us to, in our case, have individual freedoms. We celebrate as Americans individual freedom and liberty and hold that up while generally kind of taking for granted the importance of the institutions that make all of that possible. And we celebrate the people who benefit. And this is one of the classic debates within, you know, Elon Musk's world, right? The libertarians profit and benefit off of the freedom and liberty and the dynamics that make their individual entrepreneurial genius possible without giving credit to all of that institutional rigor and value. But at the same time, the institutions can be corrupting to the individuals, because they become a focus, a North Star to kind of conform identities or to shape identities, individual identities that is. So I think there's a strong interplay between the individual and the institution that is not…I don't think it's that it's not well understood, I think it's that it's often taken for granted. And I know I'm arguing out of both sides of my mouth right now, and that's where I'm conflicted. It is both enabling of individuals and it is corrupting of individuals. And so what's a healthier relationship between the individual and the institution? That’s one of the big looming questions I've been sitting with in the last couple of months. And I don't think we gave that question justice in lifting up the importance of the institution. Which is to give your question an affirmative answer, but I would take it to a whole other level if we were to rewrite the book.

DE: I feel like my understanding of how American institutions evolved is growing, really from reading in the last few years. It’s not something I had any sense of when I was younger, but it feels increasingly important to me for people to understand why institutions evolved the way they did, for better and worse. 

And speaking of evolution, I wonder if your point about the interplay of individuals and institutions gets at something else I’m curious about. I don’t know a better term for it than “mission creep.” I was reading a Foreign Policy article you wrote back in 2015 where you said: 

“America made its enemy larger after 9/11 by bundling together the Taliban, an internally directed insurgency, with the transnational terrorist group al Qaeda. In Iraq and Syria, the internal insurgency and the external terrorist threat have become one, resulting in a seemingly intractable problem. In Afghanistan, however, the insurgents and terrorists can still be addressed separately. Reconciliation, or bringing the Taliban into the political fold in Afghanistan, is the best way to prevent an Iraq- or Syria-like deterioration of the Afghan state.”

This reminded me of a year I spent doing some reporting on drug cartels in Mexico, which was also 2015, and one of my revelations during that year was that cartels, in large part, can usually just keeping doing their thing until they develop mission creep, and step over some red line in a very public way. For Pablo Escobar, it was bombing a plane that had two Americans onboard, and then he became a target for U.S. Special Forces. The cartel I was mainly reporting on, Chapo Guzman’s rivals the Arellano-Felix Organization, probably could have kept running their extremely successful business if they hadn’t accidentally killed a prominent religious official in broad daylight at an airport when they were going for Chapo. With Robespierre, maybe if he had held off on trying to overturn familiar religion; and with U.S. foreign policy, maybe if we had not “bundled” all these enemies together, things would’ve gone better. The project gets bigger and bigger. It’s almost like leaders often can’t help overshooting what they would have initially considered victory. 

So, I guess my question is: Is it inevitable that if a leader is successful, they’re always going to progress until they overstep?

JE: I think it's one of the reasons why leadership is so hard — finding that balance between something that is so visionary and ambitious that it’s a stretch goal that's going to pull in the best talent and motivate people to do things that have never been done before, like a Walt Disney or Elon Musk, versus the blocking and tackling of real budgets, and real limitations, and real technology constraints. And in Walt's case, it was [his brother and co-founder] Roy, the invisible hidden Roy who kept things on the rails and managed that tension. So I think, particularly in American culture, we do better with 51% of the weight on the maximalist kind of exceptionalism foot, where we are being hyper-ambitious in a less constrained way. 

I did an interview on your Foreign Policy part of that question recently about how that happened. Or: Why does that happen? I think in that specific case, the institution of the U.S. military has a very can-do spirit. And I think when you coupled that with the psychological weight of 9/11, you necessarily ended up with a more maximalist, unconstrained approach.

And that's why I think the talk about authentic leadership is often off the mark. Because if you get that balance right, you're pretty inauthentic as a leader, because, on the one hand, you have to play the role of the unconstrained visionary who is breaking boundaries and taking that kind of maximalist position; on the other hand, you have to kind of dial it way back into the here-and-now. Finding individuals who can manage that tension in one person is really, really hard. Walt found it in the pairing with his brother. If you're lucky, you get it right. But very often it crashes in one direction or the other. And that's why I think it's so hard to manage. Because it's asking a lot for one human brain to hold that tension with any sort of stability.

DE: Really interesting. So maybe well-calibrated leadership isn’t always what we think of as “authentic,” in terms of someone just following their intuition and vision. This is tough stuff, and I have to say, from the title of your book, I thought it was going to be sort of boilerplate leadership tips. But it was hard and nuanced, so I grappled, and I loved that. 

I want to go back to the idea you mentioned of institutions being both enabling and corrupting. I’m just thinking about that in light of how you wrote in the book about Einstein, and about how I wrote in Range about Darwin. With Darwin, there was this issue of him being a lone genius off on a boat, totally outside normal academic circles. And that’s true, but he also had 242 pen pals with whom he kept a vigorous correspondence so that he could learn about their results and ask questions. His genius was really as an aggregator and synthesizer. So I was interested to see what you and your co-authors wrote about Einstein, who is perhaps the apotheosis of the image of lone genius, off in a patent office overturning our conception of the universe. You wrote about how he also kept up extremely prolific correspondence. It reminded me of research I was reading recently that showed you can actually have too much communication in scientific research, to the point where you extinguish viewpoint diversity. You want some people on the fringes. Do you think Einstein, and maybe Darwin, had this sort of perfect setup where they were on the fringes, but with access to the mainstream via their correspondence? 

JE: Yeah, absolutely. Walter Isaacson [author of Einstein: His Life and Universe] and I got into a colorful debate about that on the 100th anniversary of general relativity. I saw him at an event commemorating the anniversary and I got into it with him. I was like, “I think you're sort of promoting the myth of Einstein as a lone genius.”  And he actually said, “That's why I wrote [The Innovators: How a Group of Hackers, Geniuses, and Geeks Created the Digital Revolution.]” He said that if he were to write [the Einstein book] again, he would downplay that. And that he wanted to kind of explore the antithesis of that in [The Innovators], where it really is kind of a manifestation of a collective. 

And that certainly was our view in our book, or my view that Einstein's genius was only made possible by that kind of dialogue with his contemporaries. But I think your point is the more refined version of truth, which is that ….you're sort of talking about team size or the complexity of the network. One of the things that I — and this isn't super related — but one of the things I thought about looking at for a while was:  Where do you get optimal emergence in complex adaptive systems? I was looking at murmurations of starlings, and I came across research that basically said that you can get massive collective coherence with a huge number of actors, where they're only communicating with like five of their neighbors. And I thought that was just fascinating. So to your point, I think size, number of connections, there's a very interesting kind of middle ground, an optimal middle ground in terms of number of connections. And, you know, this is like Jeff Bezos’s team size rule at Amazon and all that. But where I think you are going, or where I would go with that is not about the number of connections and the degree of complexity in the network, but what's the division of time between individual effort and then collision of ideas. And how do we engineer or structure the system where those ideas are colliding for maximal benefit? And that's where I think the lone-patent-clerk meets fiercely-competitive-contemporaries who were working on the same problem resulted in a great outcome. It's that kind of optimal arrangement of both. Where Einstein’s ability to generate high utility thought experiments, like the elevator in outer space, were uncorrupted by institutional bias. But then his ability to actually solve the equations of general relativity were falling on their face until he was getting essentially the equations corrected by his contemporaries. And so I actually think that's a more interesting way to frame it, that middle ground. 

DE: Jeff, thanks so much for your time. I’m going to leave it there for now because my prolix rambling has already made this long. Although I’m going to mention your book in another newsletter soon because — and here comes a sentence that has never been written before (you’re welcome ChatGPT): the way you and your co-authors wrote about Abu Musab Al-Zarqawi and Harriet Tubman reminded me of the two most prominent generals in War and Peace. There’s a leadership lesson in the comparison, but I’m going to save that for another newsletter! 

Thanks so much to Jeff for his time, nuanced insight, and his fascinating book, Leaders: Myth and Reality.

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Thanks for reading. Until next time…

David