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Malcolm Gladwell on Bold Leadership in a New World of Work

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Malcom Gladwell

Managing in a post-pandemic workplace is more complex than ever. Leaders have been required to stretch their skills in unimaginable ways and swiftly adjust their styles to meet the unique needs of individual team members.

Featuring renowned journalist and best-selling author Malcolm Gladwell, this episode will explore ways you can keep your teams engaged, productive and growing while also juggling the challenges that come with remote and hybrid workplaces.

With inspiration and advice, learn ways to lead boldly and meet the demands of the new world of work.

Transcript & additional resources for this episode below!

Malcolm Gladwell

MALCOLM GLADWELL is the author of five New York Times best-sellers — The Tipping Point, Blink, Outliers, What the Dog Saw, and David and Goliath: Underdogs, Misfits and the Art of Battling Giants. He has been named one of the 100 most influential people by TIME magazine and one of the Foreign Policy’s Top Global Thinkers. Gladwell’s book, Talking to Strangers: What We Should Know About the People We Don’t Know, offers a powerful examination of our interactions with strangers and why they often go wrong. Through a series of encounters and misunderstandings – from history, psychology and infamous legal cases – Gladwell takes us on an intellectual adventure and challenges our assumptions on human nature and strategies we use to make sense of strangers, who are never simple. He explains why we act the way we do, and how we all might know a little more about those we don’t. He has explored how ideas spread in The Tipping Point, decision making in Blink, and the roots of success in Outliers. In David and Goliath, he examines our understanding of advantages of disadvantages, arguing that we have underestimated the value of adversity and over-estimated the value of privilege. Gladwell is the host of a 10-part podcast, Revisionist History, now in its fourth season. In the weekly podcast, he re-examines an overlooked or misunderstood aspect of past events. He has been a staff writer for The New Yorker since 1996. He has won a national magazine award and been honored by the American Psychological Society and the American Sociological Society. He was previously a reporter for The Washington Post. @gladwell

Celeste Headlee

Celeste Headlee

Celeste Headlee is a communication and human nature expert, and an award-winning journalist. She is a professional speaker, and also the author of Do Nothing: How to Break Away from Overworking, Overdoing, and Underliving, Heard Mentality and We Need to Talk. In her twenty-year career in public radio, she has been the executive producer of On Second Thought at Georgia Public Radio, and anchored programs including Tell Me More, Talk of the Nation, All Things Considered, and Weekend Edition. She also served as cohost of the national morning news show The Takeaway from PRI and WNYC, and anchored presidential coverage in 2012 for PBS World Channel. Headlee’s TEDx talk sharing ten ways to have a better conversation has over twenty million total views to date. @CelesteHeadlee

 

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Malcolm Gladwell Interview Transcript:

Celeste Headlee:

Okay, I wonder, Malcolm, what kind of communication problems were you seeing in teams before the pandemic hit?

Malcolm Gladwell:

Oh. You mean for all of the 1000s of years that people have been doing teams?

Celeste Headlee:

Sure, if you can give that to me in a 40 second answer, I’ll take it.

Malcolm Gladwell:

The obvious ones, there is a tension in teams, between the efficiency of a team and the diversity of a team. So, the more the team all looks like me and thinks like me, the easier it is for us to get along, but the worse the outcome. What’s the point of having four Malcolms who all think the same thing? To the extent that I make my team full of all kinds of different voices and our outcome will be better because we’re representing more interests, more experiences, more perspectives. It’s also going to make the coordination and communication and social life of the team, not worse, but just more complicated. That is the time honored trade off in teams. And as human beings, when we get lazy, we default to making the team as functional, smoothly functioning as possible, which means filling it with people who resemble us.

Malcolm Gladwell:

I sort of feel like that has been the norm for centuries. Why were institutions run by white guys for a millennia? For a number of reasons, but the biggest reason was that because that was the easiest way to run the world. Super easy.

Celeste Headlee:

To varying degrees of success.

Malcolm Gladwell:

I’m not going to say it was a success. In fact, I don’t think it was a success. I think there were more failures and successes. But I will say, if you want to run, if you’re the British and you want to run an empire in the 18th century, you just fill it up with other aristocratic rich white guys. It’s easy peasy, it’s all guys you know, you went to school with them. If you went into a Wall Street firm in 1920, it’s what you do.

Celeste Headlee:

Don’t spoil the ending how that turned out. So then when the pandemic hit, what got worse and I wonder if anything got better?

Malcolm Gladwell:

There’s two things going on. One is that, in the years leading up to the pandemic, many institutions are finally addressing this problem and saying, you know what, the easy way out, the way of smooth running conflict free teams is not the right approach. We have to go the harder route to get a better outcome and make our teams diverse and interesting and complex. And then the pandemic hits, and I think that the difficulties associated with diverse teams get even more difficult.

Malcolm Gladwell:

On the one hand, people have been talking about, we’ve been so productive in age of Zoom, and blah, blah, blah. But there’s an awful lot of tensions that emerge when you’re not in the same space. If this pandemic were to go on for five years, I would really worry that we would just revert back to lookalike teams that are smoothly functioning.

Celeste Headlee:

Makes it sound as though you’re saying the challenges of changing the way we do business, of changing our workflows, that that’s such a high bar that the stress of the pandemic would make us simply stay with what’s comfortable.

Malcolm Gladwell:

Sure. Oh, yeah. I think so. I could be wrong, it’s just my perspective, and that’s the perspective of someone, I work in teams and I’m part of a startup that we’re trying to build a company in the middle of all this. I think it would have been so much easier over the last year if we were all in one space again, just because so much of what makes teamwork pleasurable as well as functional are those day to day interactions. It’s fun to hang out with people. And that kind of fun that comes from those intimate, not intimate, maybe is the wrong word, but relatively intimate interactions, is what makes the difficulties of diversity a lot easier to cope with.

Malcolm Gladwell:

But when you’re all in a million different places and you can’t see people and you can’t judge tone of voice, and you’re on some scratchy Zoom call, it just gets hard. So I for one will be very, very happy when this is over.

Celeste Headlee:

Since you mentioned Zoom, I think that the fact that Zoom is tiring and exhausting is something I assume most people sort of understand and accept at this point. But I wonder what you make of the data showing that we’re having more meetings and longer meetings now. What do you think is driving this urge to hold meetings and go on at length during these meetings?

Malcolm Gladwell:

Because we’ve made getting together so seemingly frictionless. It’s now just a simple matter. Before, if the expectation was the weekend, the meeting was going to be in person, we had to go to some effort to synchronize schedules and make sure people were physically there, and we were mindful of where people needed to be, so the meeting didn’t go on and on and on. Now, it’s like, if I’m working with you every day, I know that you have to go and pick up your kids from the babysitter at 5:15. So, if I’m talking to you at 5:05, I’m like, I got 10 minutes to finish this conversation with Lindsey. Whereas on Zoom, we don’t even know anymore. We don’t know anyone’s context, we just keep blabbing on. There’s no longer any kind of useful barriers, not barriers, useful boundaries, social boundaries to communication. It’s contextless communication and it is exhausting and it is omnivorous.

Celeste Headlee:

What do you mean omnivorous?

Malcolm Gladwell:

Well, just what you say, these meetings are going on forever.

Celeste Headlee:

That’s eating up all of our time.

Malcolm Gladwell:

Eating up all of our time. I’ve been trying for the longest time to get an interview with Maxine Waters for this project I’m working on. I met her once, she’s just totally extraordinary. So I was talking to her PR person, and I said, well, I’d love to get an interview. “Oh, yes, Maxine would love to talk to you. How long do you need?” And I was like, “I know this is a lot, but I’d love two hours.” And the person just started laughing. And she’s like, “You could maybe get half an hour at best.” I was like, “Half an hour?”

Malcolm Gladwell:

Then the person, it was a he, he’s like, “Well, it’s just a pandemic. You don’t understand, she has twice as many meetings as before.” Everyone knows they can get on her calendar now. She doesn’t have the time anymore. If I tried a year ago, I would have been able to get two hours. But now, everyone and his mother is calling up Maxine Waters and asking for an interview, so I’m out of luck. That’s what I’m talking about.

Celeste Headlee:

I wonder how this affects whatever advice or guidance you give to leaders, because the challenge of watching over your team members’ well being and their capacity to continue working, or whether or not they’re close to burnout, I feel like that’s changed. And yet, I don’t think that management styles have changed in order to adapt to it. What do you think?

Malcolm Gladwell:

Yeah, I would agree with that. I think we have ways of effectively managing people that have evolved over years and years and years of working in physical proximity. And then all of a sudden, we go through a year where you can’t do that anymore. And a year is too short a period for us to evolve these time tested methods of management. So we have a bit of a mismatch. And then there was a giddy period I feel like where everyone was convinced this was a better way to do things. You couldn’t read a newspaper without seeing seven stories about how we’re never going to go back to the old way, the office is dead. Real estate in Manhattan is in panic. I just read those notes like, really, you really think that’s true, that people want to be working in their bedroom forever?

Malcolm Gladwell:

The idea that you would get up in the morning, I remember my first job, first real job was at the Washington Post when I was 23 years old. The joy with which I got up every morning because I got to go to the office because the office was just so amazing. Here I was 20 years old and wanted to be a journalist, and it was an office full of 300 people who were amazing journalists. Why wouldn’t I want to go into the office every day. It was amazing. I would sit there and just listen.

Malcolm Gladwell:

Bob Woodward sat two rows over from me. I just watched him. It’s like a masterclass, right there, right in front of me. The greatest journalist of my generation was 10 feet away making phone calls and I was 23 years old. I had no idea what I was doing, like it was amazing. Today, the idea of having that same job and I would be in my pajamas in my bedroom, and I couldn’t see anyone else and learn from anyone else, it’s nuts. Of course, I want to go back to the office if I’m 23. I’m in the office right now, I’m 57. I’m not working at home right now.

Celeste Headlee:

Are there then lessons to take from the pandemic? I assume that it won’t be long before we’re beginning to transition to something else, which may not be A. Pre-pandemic habits, and may not be B. Pandemic habits, but might be C. a melange of the both. And I wonder what lessons do you think we can take away from both the things that worked well and especially the things that haven’t worked?

Malcolm Gladwell:

Well, you know, I was just doing an interview before I talked to you with this really wonderful author, and he had written this book which I’d loved. And he talks about a very famous, it’s about a very famous police chief in the 50s. And at one point, I asked this guy, I was like, “Did this police chief, was there any joy in his work?” And the guy I was talking to who had written a book about this chief, it was clear that no one had asked that question of him before, and he hadn’t thought about it. And he was like, “You know what, there was no joy.” And that explains a huge amount of how this police chief went horribly wrong in the way he did his job. That question of whether there is joy in your work has always been one that’s been central to me. To me, that’s the point of work.

Malcolm Gladwell:

We started this little company, Pushkin, two and a half years ago. And when we sat down and tried to figure out, and we had three employees, whatever, what our company principles were, make cool things, and the second one was have fun, there has to be joy in what we do. And if you’re not having fun, it’s pointless. Just go work in a coal mine. There’s plenty of joyless jobs in the world. If we can’t provide joy to our employees, we’re failures. My worry about this pandemic phase is that idea of the importance of joy got forgotten. I do not think you can have joy making one Zoom call after another from your bedroom. There’s no joy in that ultimately. Maybe for two months, but it doesn’t work as a long term strategy for having fun.

Malcolm Gladwell:

Like I said, if we’re not having fun, we’re failures in this business. That’s the part of this that I hope comes back really fast when everyone reorients and says, are we enjoying ourselves, and if we’re not, let’s figure out a way to get that back into the workplace.

Celeste Headlee:

I’ve been fascinated by the struggles to maintain engagement as we work remotely, and how so many of them have fallen flat. One of the primary ways some managers have used to engage employees is through making Zoom fun or scheduling social events or like trivia nights on Zoom. It hasn’t gone very well. I feel like that kind of tells us something about global companies or people where their employees and their team members are not headquartered in the same place. You’re talking about working at NPR or at a newsroom. I work at NPR, I know that when you’re working in a newsroom, you can have colleagues all over the world. I wonder what we’ve learned about engagement. Have we learned anything new about how to keep people engaged when they’re not in the same place?

Malcolm Gladwell:

It’s funny, I have done for the last 20 years a lot of speaking at conferences, industry conferences of one sort or the other. When I began 20 years ago in giving those kinds of talks, I will admit I was slightly cynical about them. I was like, it’s a bit of a scam. People all go to Phoenix in March, play a lot of golf, and then they come in, and I’m just there to entertain them, and then they go off and do their own thing. Over the years, I’ve come to have more and more respect for what the purpose of something like that is. It has multiple purposes, but one of it is the thing you were just talking about, which is engagement, which is, what a conference does is it takes you for a moment out of your very specific world and throws you into an environment with lots of other like-minded people who are in different contexts and face different challenges. And it’s a really efficient and fun way of recharging your batteries.

Malcolm Gladwell:

It’s like, you can be a math teacher in an inner city school somewhere and you’re exhausted and you’re unsure about whether you making a difference. And then I take you out and I put you in a conference of math teachers and there’s 1000 people in the room. And you’re going to have 20 conversations over three days with other people and realize everyone’s got the same struggles as you do and they have all kinds of interesting ways of resolving those struggles, and you can learn from them, and they can learn from you. And you realize you’re suddenly a part of a community. And you go home after three days, and your job seems a lot different. And that process is repeated hundreds of times over the course of a normal business year because there are, 100s, 1000s of times, because there’s tons of these conferences.

Malcolm Gladwell:

And they also function. Typically people in the workforce work really, really hard. They have families, they don’t get a break of any kinds. And you can give them a functional break at a conference where they could talk about their work, which they love, but in a setting that makes it feel like it’s fun. And then they can go play around golf, or go swimming, or hang up at a pool, whatever. That kind of stuff, we’ve really missed that. I mean, that stuff went to zero over the last year. It will come back and it’ll make a big difference on this question of engagement, because it will help people find a way to recharge their batteries. I think of conferences as being a huge part of what it takes to maintain productivity in the workplace.

Celeste Headlee:

It’s interesting you say that because I was just interviewing a CEO who said she can’t imagine spending the same amount of money anymore to send people to conferences. Her rationale was now that we know we can do it virtually, why would I pay for travel and hotels?

Malcolm Gladwell:

Such a mistake.

Celeste Headlee:

Why?

Malcolm Gladwell:

I mean, have fun keeping that employee after four years of that. You’re asking someone to commit their energy, their imagination, their everything to your job. You’re now going to make them, and you had an institution, an annual institution that was set up that allowed them to interact with, socially interact with other people in the same space in a nice environment, and get a new perspective on their work. And now you’re going to say no, actually, I want you to sit in front of your computer even more instead. It’s nuts.

Malcolm Gladwell:

The point of work is not to maximize productivity in the short run, and the point of work is not to extract every last dime you can out of your employees. When did that ever work? Show me when that strategy ever worked in the long run? Never, ever, ever.

Celeste Headlee:

And yet, that idea of sort of squeezing every last minute out has kind of influenced management styles for a long time. This idea of, and it’s sort of how we’ve all become addicted to productivity, this idea of having people answering emails even when they’re on vacation, or not taking vacation. I myself have been in a workplace where you have a manager say, we’re really busy, don’t even think about taking vacations right now unless somebody died. That really has been a strategy. We were already heading toward a burnout epidemic worldwide before the pandemic hit. What do you make of the state we’re in now?

Malcolm Gladwell:

It’s nuts. I remember when my mom went back into the workforce in her 40s, got a job, went to her boss and said, “I know you want me to work five days a week, but I’m not going to work five days a week, I’m going to work three and a half days a week, and I promise you, I could do more in three and a half than everyone else can do five.” Her point was not that she was Superman, though, she’s kind of Superman, her point was look, like, if I’m happy and well rested and can do all the stuff I want to do on the side, I’m just going to be more productive. You don’t need me to drag out my work over five days. I’m fine with doing three and four, three and a half. And she was right. I just think we’re underestimating the value of rest.

Malcolm Gladwell:

I’m a runner, and the first thing that they tell you as a runner is that you don’t — hold on, I’m going to get this right. You don’t rest because you run, you run because you rest. In other words, you get better in the rest period between runs. That’s what allows you to improve is the fact that you consolidate your training gains by doing nothing, by getting away letting your body come back stronger. Runners understand this, but I don’t know why if runners, we’re not the brainiest most sophisticated people in the world, but we all grasp this fact, take a day off, you have to. I don’t understand why bosses somehow think that’s an anathema.

Celeste Headlee:

Yeah, I’ve never understood that either. But we are in this situation where people are burning out. The data shows us that people are actually working longer hours when they’re working from home than they did when they went into the office. We have on top of that a lot of exterior stressors that are adding to people’s anxiety. We have not just the pandemic but politics have not been particularly restful right now. There have been financial issues. I imagine there’s a lot of employees or a lot of leaders who are looking at their team members and worried about their well-being. How would you suggest managers and supervisors support well-being among team members right now?

Malcolm Gladwell:

I’m not going to answer the question exactly as you post it. This has been a very useful exercise for us to think about what our priorities are as a country. So, to my mind, the biggest issue in the last presidential election was this thing that you’re just talking about, that we just have, for the last nine months, we have put many groups in society, but particularly parents, middle to lower income parents of school-aged children, we’ve essentially asked them to do the impossible because we decided for a combination of reasons, some good, some bad, I would say more bad than good, that we were just going to arbitrarily shut the schools and not give parents any other option.

Malcolm Gladwell:

So in addition to keeping your life together in the middle of a pandemic, many people with a great deal of workplace anxiety, that was redoubled in the course of the pandemic. We’re also going to make the logistics of your life 100 fold more complicated and stressful because your kids are going to be at home. The idea that that wasn’t the single most important problem facing the country in the fall of 2020 baffles me. And that’s a problem. If I was the CEO of a major corporation, I would have stood up and I would have said, no, wait a minute, we have to have a conversation about this right now because you are taking the most precious resource in this country, which is the workers of this country, and you’re putting many of them through living hell. And the function of government is to relieve those kinds of burdens, that’s what government is, that’s why we have it. And if government’s not going to read those burdens, then I’m not really sure why we bother.

Malcolm Gladwell:

And I didn’t see that conversation. I saw a lot of jurisdictions behave in ways that were fundamentally irrational. I saw places that were more willing to open restaurants than schools. That’s nuts. Nuts.

Celeste Headlee:

I mean, it’s interesting that the conversation has turned this way, because I did want to ask you about sort of the disproportionate effects of COVID-19 and the economic crisis that we’re in right now because you’re talking about schools, and we know looking at just the employment numbers, that the crisis with childcare has fallen more on women than on men. We know that the COVID-19 pandemic has affected people of color in larger numbers than white people. And so, the inequities that we were already discussing pre-2020, the pandemic has simply exacerbated them, in some ways, disastrously. I wonder how leaders can respond to this. Is there both an ethical and also effective way to respond to this?

Malcolm Gladwell:

Yeah. I’m thinking of someone who’s part of our company who is a mother of young children and who I just know her life logistically has been insanely complicated over the last eight months. Every time I get an email from her, I look at the time the email was sent, it just tells you everything. The timestamps tell you absolutely everything you need to know about her life right now. That’s the time she has to do her work, it’s like the wee hours of the morning, got one today at 6:33AM. And I know she didn’t go to bed at 9PM. Leaders have to be obviously, and I think we’re trying to be as sensitive as we can to those kinds of predicaments.

Malcolm Gladwell:

I want to go back to the point I was making earlier that there is a limit to what leaders of individual companies can do about those kinds of problems. These are social problems that our government has to address. And like I said before, that’s what government is for. We have gotten distracted by a series of debates that have nothing to do with day to day lives of most Americans.

Celeste Headlee:

Can you give me an example of the distractions?

Malcolm Gladwell:

I mean, sure. I’m thinking back to the November elections in this country. If you just analyze the political rhetoric of both sides and you see how much of it was addressed to these kinds of very day to day prosaic concerns of working Americans, it’s very little. You look at the way that, we did finally have a conversation, we had an initial round of stimulus funding, and now we have a second round of money that’s intended to help out. But how sloppily that money is targeted. It seems we’ve just gotten one of those leaf blowers and we’re just blowing dollar bills over the country without pausing to say, the effects of this pandemic on people’s lives are wildly disproportionate.

Malcolm Gladwell:

There are as many people who have said this has been the best year of my life who have said this has been the hardest year of my life. Some people, it’s been fantastic. We should at least be able to discriminate between those two groups when it comes to helping out. Or if you look at the sort of preoccupations of popular culture over the last few months. I don’t need to rehash those kinds of controversies. There’s nothing wrong with those controversies per se, but I don’t know why of all times we’re having those discussions now. Can we at least wait until we’ve addressed the much more pressing concerns of lots of people in this country? There’s a little bit too much concern about what people are or not saying on Twitter, and not enough concern about these kinds of everyday issues in people’s lives.

Celeste Headlee:

I mean, I think also people are reevaluating a lot of things, not just these kind of inequities and the roots of them. I find there’s been a broader discussion about what kind of traits one should look for in a leader. There’s been a lot of discussion about how some people may have attained their positions not based purely on merit, not just based purely on their strengths and their talents, but also on preferences and systems that support them over somebody else. I wonder if you have a new list. Have you, in your mind at least, an idea of what a modern leader needs at their disposal? What their talents should be?

Malcolm Gladwell:

Interesting. I guess I would say, I am less and less convinced that there is a single definition I guess I would say. And particularly the older I get, the more I’m aware of how lots and lots and lots and lots of different leadership styles can work. It depends on the fit to the organization, or just depends on how well that leader in question articulates their way of doing things. There are times, I’ve always thought, someone once said to me years ago about schools, there’s 100 different educational philosophies. They all work if they’re just done honestly.

Malcolm Gladwell:

You can have a law and order school and you could have a super permissive school, and both of them can educate kids really well. It just depends whether the people who are in enunciating that, articulating that philosophy. Do it in good faith, honestly and competently. I sort of see the logic of that. I’m more and more not about what you’re doing, it’s how you’re doing it. My way of getting to more diverse leadership is, let’s not get so hung up on defining what we want in a leader, but more hung up on how someone is choosing to make sense of that leadership philosophy.

Celeste Headlee:

So that leads us to talk about your new book. The new book, Bomber Mafia, seems to sort of grapple with some of these issues of morality and how we make decisions and what we do with leadership when it’s sort of thrust upon us I think. How did you get to this story about World War II and a Dutch genius typing away on a computer?

Malcolm Gladwell:

You would think that every story from World War II would have been told by now. Turns out, no, there’s still some ones out there. I just became fascinated by this little group of pilots in Central Alabama in the 1930s who had a dream about how to reinvent war. They were all people who had been through the experience of the First World War and seeing the kind of extraordinarily senseless carnage of that conflict. And they were like, we can’t do that again. There must be a better way for us to use violence to settle human conflict. And they came up with this kind of dream about, if we can just drop bombs with perfect accuracy, we won’t need armies on the ground anymore, we won’t need to destroy entire cities, we can just take out a handful of select targets and our enemy will give up and super peace.

Malcolm Gladwell:

The dream turns out to be …

Celeste Headlee:

A nightmare.

Malcolm Gladwell:

Yeah, it doesn’t work. But I love that they tried. But I think that’s what attracted to me. They’re a group of people who articulate a better way to do some complicated task. It turns out to be premature. I mean, we finally enact their vision, but just 70 years later, not when they were dreaming it, two generations later. There’s this cast of characters, and I focus on this one guy named Haywood Hansell, who is deeply romantic. His favorite book is Don Quixote because he’s the knight who tilts at windmills. I mean, he’s just this guy who has this fanciful, romantic, utterly impractical vision about how he’s going to change warfare. It ends with him leaving the air force in disgrace.

Malcolm Gladwell:

I think he’s a hero because somebody had to stand up and say, there’s a better way to do this. And someone had to be the one to fail so that others could succeed down the line. We celebrate as heroes the ones who finally make it work, but I wanted to celebrate as a hero the guy who tried it and failed and allowed others down the line to figure out how it worked. That struck me as being really important. In other words, to tell the full lifecycle of a moral innovation, starting with when it didn’t work.

Celeste Headlee:

It’s interesting to me, and the reason I connect it with this discussion of leadership is that what you have done in this book is sort of point to the value of failure. And not only that, but hold up as strong people who can embrace the failures of the past, or at least admit to the failures of the past, and be willing to fail again. And that is a relatively modern value. We in the past have lionized leaders who were decisive and who wouldn’t admit to error because that would be showing weakness.

Malcolm Gladwell:

Yeah, yeah. I will admit that a lot of this is my own kind of romantic attachment to people who tilt at windmills, I’m very fond of them. That notion of can we build into our understanding of leaders some expectation about their frailty and a willingness to stay with them through failure. That strikes me as a really interesting notion.

Malcolm Gladwell:

Some professions do very much embrace that model. And other professions are quite hostile to failure. I find myself more and more drawn to the professions that tolerate it, that understand how important failure is in the kind of evolution of our practice. I’m a huge basketball fan and professional sports is really interesting because they are super tolerant of failure. If you’re an NBA head coach and you get fired, you’ll almost certainly get another job. You have to fail, you got to screw up badly, three or four times in a row before they’ll get rid of you. I used to think it was a bad thing, now I really like it.

Malcolm Gladwell:

It’s just about second chances. It’s like, they’ll roll the dice. And I feel like if you have a world that’s willing to rehire a failure, ultimately, I feel better about the chances of that same world rehiring someone who looks different, or who’s utterly unconventional. Maybe that’s naive of me. I think we will get a female head coach in the NBA real soon. There’s a woman who now, I think she’s with the San Antonio Spurs, who people are now talking as a potential head coaching candidate. If that happens too, and it looks like it might, that is a product of a forgiving culture. It’s like a culture that says, we don’t really know what a successful NBA coach looks like, so we might as well give people second chances and also hire people who don’t look like traditional NBA coaches.

Celeste Headlee:

I think you’re talking about Becky Hammon, who took over when Gregg Popovich was thrown out of the game.

Malcolm Gladwell:

Yeah, Becky Hammon. Maybe Becky Hammon opens the floodgates. The kind of 24 year old guys in the NBA, he doesn’t care whether his coach is male or female. That generation doesn’t have a hang up about that. I worry more about the owner of the team. Players will play to someone who knows basketball and treats them with respect. We’ve already solved that particular problem. So yeah, I’m optimistic about that kind of culture.

Celeste Headlee:

Have you changed anything about the way you work or lead because of the past couple years?

Malcolm Gladwell:

Calling me a leader is a stretch. So I started this company two and a half years ago with my best friend, Jacob. He does all the leading. I just make stuff. The difference is, for the bulk of my career, I was a writer who worked alone, and now I do audiobooks and podcasts and I work with a team. So for the first time I have had people actively helping me, and I’ve discovered I really like working in a team. But I didn’t know what teams were like before because it was never part of one. Now I’m part of one and I think it’s kind of fantastic. I’ve figured out how much you can benefit from, sounds ridiculous that at my advanced age I should be saying this, but I did discover at my advanced age, that you’re just a lot better when you are surrounded by people who have different skills than you and different experiences and different ways of thinking about things.

Malcolm Gladwell:

The story I always tell, I’ve told it many times now, but my producer for Revisionist History, the first producer we ever hired, who’s now the editorial director of our entire company, when we were interviewing her for the first time, I read her all of the stories I was thinking of doing in the first season of Revisionist History, and she looked at me and she’s like, “If you do all those stories, no woman will ever listen to Revisionist History.” And I was like, oh, I really need to hire this woman because if I don’t hire her, you know, I was not aware of this fact. I was like, oh no, God, what am I doing? So we hired her on the spot. You need to come and fix this problem. Hadn’t occurred to me to that extent, to that point, how narrow my story ideas were, because it’s just me, things rattling around Malcolm’s head. Malcolm’s one guy with very, very particular tastes. And in that moment, when I was interviewing Mia, her name is, I was like, I discovered, really, really helps to have someone who doesn’t have your head in the room.

Celeste Headlee:

Which brings us back to where we started this conversation, which was sort of the value of diverse teams.

Malcolm Gladwell:

There’s just no question how much more powerful, how much better that, I had this discussion. In my last book, Talking to Strangers, I had that whole chapter on the Jerry Sandusky case at Penn State. I was of the opinion that I don’t think the leadership of Penn State deserve to have been fired or put in jail. I think they made mistakes that we would all have made in their shoes. I don’t think they were complicit in the crimes of Jerry Sandusky. That said, had they had a more diverse leadership team, I wonder whether they would have acted differently.

Malcolm Gladwell:

In other words, it’s probably not a good idea if you are running a 21st century university to have a leadership team that is all white guys who are your age. I think that’s part of why they got in trouble. And I’m not saying that they needed to have, I’m not even using traditional definitions of diversity here, but having a mother on the leadership team, having someone who had been through problems of sexual assault or sexual harassment in the past as part of their leadership team, having someone who had been through a similar kind of scandal at a previous school. Just having someone who had a set of experiences outside the set of experiences represented by the leadership team of Penn State, that would have been super useful. And that may have allowed them to resolve that problem in a way that did not land them all in jail.

Malcolm Gladwell:

There’s a way to kind of say, to hold those two things simultaneously. I don’t think those guys at Penn State did anything wrong. At the same time, I think there was something deficient in the way their leadership team was structured. And that should be a lesson to lots of other leadership teams that there’s a value in having a wide range of perspectives at the top, because it will really help you when a really thorny, difficult problem comes along. And that’s what they faced, a really thorny, difficult problem, a one in a million case of a seriously bad apple in their midst that nobody was anticipating or had any experience with.

Malcolm Gladwell:

I’m very happy that Joe Biden has a his co-president, someone’s a lot different than he is. I’m quite happy with a 78 year old white guy is my President, but I’m not happy with two 70 year old white guys in the White House. That’s a problem. I’m glad there’s a little bit of …

Celeste Headlee:

As you should.

Malcolm Gladwell:

I’d be even happier if they reversed roles. Biden strikes me, he’s a great Vice President. I think Kamala, ultimately I think, I’d rather have her as top chair. Let’s just wait four years for that.

Celeste Headlee:

Always an interesting conversation, Malcolm. Thank you so much for your time.

Malcolm Gladwell:

Thank you. That was really fun.





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