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Why the Best Leaders Don’t Always Have a Plan

Career Entrepreneurship
Why the Best Leaders Don’t Always Have a Plan


  • Why we often pick the wrong leaders
  • Why a four-star general needed to think like a gardener
  • Why even Al Qaeda’s leaders have admirable qualities

Stanley McChrystal is a retired U.S. Army general who commanded the Joint Special Operations Command (JSOC) in the mid-2000s. He is also senior fellow at Yale University’s Jackson Institute for Global Affairs, and the bestselling author of the recently released book, Leaders: Myth and Reality. World-renowned organizational psychologist and Next Big Idea Club curator Adam Grant recently hosted him at Wharton to discuss how we can cultivate more female leaders in the world, and why so many of our beliefs about real leadership are off the mark.

This conversation has been edited and condensed. To watch the full version, click the video below.

Adam: In Team of Teams, you wrote that [when you stepped in to command the JSOC,] you stopped thinking like a chess master and became a gardener. You’re a general who’s known for being a fierce leader, and you’re saying we’ve got to go garden? Seems like a soft metaphor. What’s behind it?

Stanley: I had thought that leaders were responsible for directing, having an answer to every question, giving orders, driving performance. I was pretty good at that for most of my career, but suddenly in this environment, that wasn’t enough. When we got up to 18 raids a month, I was still personally approving every operation, but that was the absolute limit. The wheels were falling off the machine, so we had to change.

The first thing is that I had to share information that I didn’t share before. The information which had been curated for me, the leader, had to be turned on its head and shared with everyone. Then I had to give the decisions down [to others]—that’s a little scary, because you’re still responsible.

In the summer of 2004, the opportunity to change was no longer optional—it was change or lose, and we had no idea how to change. I wasn’t Steve Jobs—I didn’t have this vision. All I knew was that the current course of action was failing. So I said, “We’re going to keep doing more of whatever works, we’re going to stop doing what doesn’t work, and you, the organization, will figure it out.” And that’s essentially what happened.

I had grown up on the idea that the leader is a chess master. You move the chess pieces, and if you’re a good strategist, you’re going to win. But the reality is that I’d become more like a gardener. A gardener doesn’t really grow anything—plants do all the growing. But a gardener creates an environment in which plants can grow. So you can change your goal pretty significantly if you become a caretaker of an environment, and allow everybody to operate there.

Don’t think that I suddenly [started walking around] and rubbing everybody’s bellies. I leaned on the organization harder. But the point is, I’m not a limiting factor—I’m a cheerleader, I’m an orchestrator, I’m an enabler.

And people own it when you push it down like that. Before, if I said, “Okay somebody go out and do something,” they might do it to the best of their ability. But if you say, “We need to achieve this—figure out what we need to do, and make the decision to do it. Let me know how it goes,” they own it with a very different mindset. It’s extraordinary how most of the organization was very comfortable with that. There were some who would struggle with accepting that, but the good ones take it and run like crazy.

Adam: It’s such a fascinating contrast to the standard models of change that say you’re supposed to define a problem, build a core change team, and then immediately roll out a vision. You’re saying no, actually go in with no vision—just tell people you’re changing [as an organization] and let them figure that out. Do you think that works outside of the military, too?

“We elect, select, follow, promote, support people who are serial failures, and we do it because they fill some emotional need in us.”

Stanley: I think it does. Both vision and strategy are something you have to be a little careful about. The vision should be general—“We’re going to win!”—but the strategy needs to be flexible, because things are changing fast in today’s world, and the strategy won’t survive too long. You shouldn’t let the strategy be handcuffs that hold you.

Adam: In your new book, you wrote, “Leaders who exhibited all the right traits often fell short, while others who possess none of the characteristics of traditional leadership succeeded.” This is something that’s bothered me for my whole career—we think about qualities that we know are critical for leadership, and some of those don’t seem to be enough. Then we see people who lack those qualities rise, and sometimes even succeed. How would you explain that paradox?

Stanley: We think that if we have the right traits, learn the right behaviors, and have the self-discipline, we’re going to be successful. That’s just not true. You can follow all the rules and completely fail. Someone who breaks every rule and is offensive to you may beat you, because leadership isn’t what we think it is, and it never has been. It’s so much more contextual than we want to believe.

We tend to think of leadership as influencing people to do things they wouldn’t otherwise do, but [in my new book,] we backed away from that definition. We now think that leadership is an emergent property from the interaction between followers, leaders, and other contextual factors. Leadership isn’t something that the leader carries in a bag and sprinkles on people. We want to think, “If I’ve got the traits, I’m a great leader.” But a leader who’s got all those traits has almost the same probability of failing as someone who has almost none of them.

If a leader is very effective in one company or organization, and the headhunters go find him, pick him up and take him to another, they fail more often than if you just hire some character from inside the company and bring them up. And you say, “Well, what happened? Did old Stan just lose his stuff, or is Susan just not as motivated as she used to be?” No—the context is different. What worked in another context doesn’t work [here].

A second myth is that the leader is responsible for everything the organization succeeds or fails at. In writing my memoirs, I found that I had been given credit for a lot of things that the organization had done, and I was happy to accept that. I’d made decisions and something had happened, and therefore, I must have been the reason, [right?] I had this simple view of what happened, and in reality, all these other players had done things that I never knew about. I assumed that I pulled the right lever, and X happened. In reality, I pulled a lever, all these [other] things happened, and X happened—but it was only slightly related to me pulling the lever. I mattered, but not nearly as much as I thought I did. As we applied that [idea] to these other leaders, it gets proven over and over again.

Martin Luther is credited with starting the Protestant Reformation. The Protestant Reformation is starting, Martin Luther nails 95 theses to the door—in fact, its questionable whether he actually did that—and he becomes part of it. He matters, but he’s not the Protestant Reformation. And you can apply that to almost anybody. This [narrative of the] great man or great woman as the essential player just isn’t played out in history.

“Don’t get disappointed when you find flaws, but at the same time, don’t look at someone and pretend there aren’t any.”

Lastly, we have this myth that says we demand results from our leaders, that we only follow people who get a good bottom line, win victories or elections or wars. But we don’t—we elect, select, follow, promote, support people who are serial failures, and we do it because they fill some emotional need in us, and we make allowances for it. We make allowances for all kinds of things, because it’s the relationship between the leader and follower—the emotional connection, how they look and make us feel—that’s so incredibly important.

So when you put all this [together,] you realize that we look at leaders through this really foggy lens. All those things we knew about selecting [leaders]—and even leading ourselves—is deeply flawed.

Adam: I love that you’ve called out the romance of leadership—leaders are less responsible than we think they are. I think that’s good news for all of us who are not in leadership roles—seems like bad news for leaders, though. How do you think about what real impact a leader has?

Stanley: I still think the leader matters a lot, but more for setting tone than anything else. When you’re a senior leader, people tell you how important you are. “You’re humorous, you’re brilliant,” that sort of thing. You start to believe that, and our media supports that, because our media wants to put people on pedestals. We do the same thing with social media—we’re constantly looking for someone who will lead us.

What we need to do is look in a mirror, and say, “Wait a minute, we’re [not just] followers. We’re participants, partners.” We have responsibility, we have much greater agency than we want to pretend. We can’t just tell a leader to show us what they’ve got, and then decide whether they succeed or fail. We are much more of that than we like to pretend we are. And when leaders fail, we own that, too.

Adam: I couldn’t believe that the book opened with Robert E. Lee, and then my second surprise was that you grew up admiring the man. You’ve obviously changed your tune on that, but I’m curious: How do you think about studying a flawed leader, and whether we should actually take any insights away from them?

Stanley: That’s the only kind of leader you can study, because there aren’t any leaders that aren’t flawed. You’ve got to look holistically—don’t get disappointed when you find flaws, but at the same time, don’t look at someone and pretend there aren’t any.

The good things about Robert E. Lee were very good. He was a studious young guy, he was a great young officer, he was offered command at Union forces in the beginning of the Civil War, but ultimately sided with Confederacy. He performed bravely on the battlefield—some of the most amazing battlefield feats in American history. But at the same time, he betrayed his oath to the United States, and spent the next four years trying to destroy the country that his role model, George Washington, had helped create. And he did it to defend the institution of slavery.

I have to come [to see] Robert E. Lee as, in some ways, very admirable, and in some ways an absolute failure. When we look at leaders, we don’t have to be forgiving, but we have to understand that [leaders are flawed]. That’s what you can expect. [Take] a leader that you abhor, like Abu Musab, the leader of Al Qaeda in Iraq—I abhor so much about him, and I was happy the day we killed him. But the reality is, I admired a lot about the way he lived. He died for his cause. I disagree with what he believed in, but it was genuine. As you approach [learning from leaders], we try to take good or bad away from the moral [judgments] and say, “Are they effective or not?”

“The person you’re going to have to live with longer than anybody else is you.”

Adam: You write that the history of leadership is mostly a patriarchal history.

Stanley: We wanted to have as many women as we could in the book—we ended up with three. If you go back in history, it’s harder to find women [leaders] simply because the opportunities weren’t there. And then you say, “It’s a lot better now.” Well, in the United States, there are more male CEOs named John than there are women CEOs entirely. We have a problem.

So you have to do several things. You have to go back and create [leadership] opportunities [for women] from a young age—otherwise they’re not going to be postured for success. The second thing is you have to have female role models at the senior levels, which gets back to chicken or the egg: “How do you get senior role models unless you fix the problem… So how do you fix the problem? Let’s get senior role models!”

Some of that has got to be the equivalent of affirmative action. If you wait until it happens naturally, our children’s children won’t get there. So there’s a legislative change, and then there’s a cultural change. The cultural change takes longer, but it’ll stick more when it finally occurs.

Adam: How do you show leadership even if you don’t have formal authority?

Stanley: The best thing you can do is be an exemplar, exactly what you want your leaders to be—mature, thoughtful, etc. You’ll find that there is an effect of subordinates shaming senior leaders into functioning better. When I was in the Army Rangers, it was the first place I’d ever been where I was a captain when I entered. We had really strict discipline, and if I stood somewhere and put my hands in my pockets, a [private] would walk up to me and say, “Sir, we don’t put our hands in our pockets.” That’s really powerful. If you walk the walk yourself, it’s amazing the effect you’ll have on leaders.

Adam: If you were to give one piece of advice for a career or a leadership journey, what would that be?

Stanley: There’s a great piece that C.S. Lewis wrote back in the 40’s called The Inner Ring. The argument that he’s making is that there’s an inner ring in all kinds of things in life, and the inner ring is what we, almost by human nature, want to be in. It can be getting accepted to Wharton, it can be joining the cool group in school, it can be becoming the managing director in an organization—it’s some ring we want to get membership to.

And the pull of wanting to get into those inner rings can make you do a lot of things that you shouldn’t. If you’ve ever been in a group of people, and they tell a joke that’s clearly unfair or cruel to somebody else and you laughed—not because you thought it was funny, but because you wanted to be accepted by that group—that’s the danger of the inner ring. And it’s incredibly powerful.

Not all inner rings are evil, but be really cautious about it. Because the person you’re going to have to live with longer than anybody else is you. My litmus test now is my two granddaughters. They live next door, and I don’t want anything I write or do to be something that they are ultimately ashamed of. No amount of money, no amount of success, no amount of anything is worth giving that up. And if you hold on to that, everything you don’t get in life will seem unimportant, because you’ll be able to live with yourself.

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