CEOInterviews.AI
Start App
Michael Lynton
Board member, Independent Board Member

Malcolm Gladwell, Michael Lynton and Joshua Steiner in Conversation: From Mistakes to Meaning

📅 Mar 10, 2026 The 92nd Street Y, New York 55 MIN 505 VIEWS 238 SEGMENTS · 3 SPEAKERS
Join Michael Lynton, former CEO of Sony Entertainment, and Joshua Steiner, former US Treasury Department Chief of Staff, for a conversation with Malcolm Gladwell about transforming failure into discovery — and Lynton and Steiner’s new book, From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You. We all make mistakes. Longtime friends Michael Lynton and Joshua Steiner made mistakes that shaped their careers and lives, but it wasn’t until the isolation of the pandemic that they began to open up to each other about them. When Lynton was the CEO of Sony Entertainment, he greenlit the fi...

Questions asked in this interview

12
  1. 0:08Josh, Michael, is this your first time on stage at the Y?
  2. 5:29One is, what do you mean by a mistake?
  3. 8:46How did you manage to convince so many people to talk about them?
  4. 13:34And Michael's like, 'What are you talking about?
  5. 15:50So, just quickly describe the process for greenlighting a movie. How did that work?
  6. 16:22And did you in this case?
  7. 18:04Was there a moment in your life previously where you thought to yourself, I really want to be part of that crowd?
  8. 23:09Does it open up a whole new set of questions for you?
  9. 31:50And the whole question is, is the bus driver at fault or whether it was just terrible weather?
  10. 33:51Why is this person getting a pass?
  11. 37:51And there's an aspect of what you're describing, right?
  12. 42:32... read the book, they say, 'Well, why didn't you do this?' or 'I've been thinking about this.' And it's such a broad area and when we started to do this we assumed like, good idea, there are 14 versions of it already out there, aren't there?
Malcolm Gladwell 0:05 ↗
Welcome to the Y.
Josh Lieb 0:06 ↗
Nice to be here.
Malcolm Gladwell 0:08 ↗
Yes. Josh, Michael, is this your first time on stage at the Y?
Michael Lynton 0:14 ↗
It's certainly mine. Is it yours, Josh?
Josh Lieb 0:15 ↗
That was a violin solo I did several years ago. Malcolm, were you not here for that?
Malcolm Gladwell 0:22 ↗
Well, it's a right of passage in the New York literary world to be up here.
Josh Lieb 0:28 ↗
I like the use of the word literary.
Malcolm Gladwell 0:30 ↗
Yes. Well, that's a strong start. We are here to discuss the book the two of you wrote about mistakes, and it's an extraordinarily rich topic for discussion. But I wanted to start with how the idea of this book came about, because I have some questions. But let's start there. You two have known each other for a very long time.
Michael Lynton 1:00 ↗
We have. Yeah. For a while.
Malcolm Gladwell 1:02 ↗
Did you meet?
Michael Lynton 1:03 ↗
You know, we've been asked that question and I honestly can't remember, but it's been a while. It's been about 20 years or more than that.
Josh Lieb 1:10 ↗
Yeah. But this book started when it was right around the pandemic and we were taking a walk and Josh said, 'I have an idea for a book.' And basically what he said to me was, 'Look, I would like to really explore the subject of mistakes. I know you have a big mistake that you've made because Josh was very much part of it and I have one.'
Not responsible, to be clear.
Michael Lynton 1:33 ↗
Not responsible.
Josh Lieb 1:34 ↗
Okay, let's just be clear.
Michael Lynton 1:35 ↗
He was helpful to me at the time. And he said, 'I think it would be a really interesting thing to explore, but I think it would also be really helpful to us both if we sort of investigated why we made those mistakes and how we dealt with them.' And that was sort of the impetus for it.
Malcolm Gladwell 1:51 ↗
Yeah. Now, you had not had a conversation before that in which you had gotten into the principal mistake you felt you'd made in your career.
Michael Lynton 2:02 ↗
I don't think so.
Josh Lieb 2:03 ↗
No, I think we hadn't discussed it really. And before we start, we should thank all of you for coming. You got a lot of choices in New York and some questionable judgment. But so, and thank you Malcolm. Thank you. We'll get to it. Malcolm is an important subject in this book. We'll get there. All right.
Malcolm Gladwell 2:18 ↗
Okay. But just you know what happens if you don't get it out there quickly?
Josh Lieb 2:21 ↗
The time will go by and he will evade it. So we're going to get there. That's probably why you came. So we had talked about it when you were in the middle of this crisis. And I think we hadn't talked about it since. And I would ask Michael about it occasionally. I would sort of nudge my way towards it and he would evade it. And it was that moment when someone manifests the behavior that you don't like in yourself and it's super upsetting. So I saw in Michael the same thing I had been doing. I had made a bad mistake. Anyone who wanted to talk to me about it, I pushed aside. I joked about it. It was just completely off limits. And you were doing the same thing. It bugged me.
Michael Lynton 2:58 ↗
And it was probably because it bugged me because I was doing the same thing.
Malcolm Gladwell 3:01 ↗
Do you think so? Let's talk. I'm curious about this. There is a version of this where our mistakes are the things that are kind of constant conversational fodder, right? Explain to me why it would be the case that neither of you are—you're both introspective, thoughtful people. It's not like you're blocked or massively insecure.
Josh Lieb 3:23 ↗
To a degree, but yeah.
Malcolm Gladwell 3:25 ↗
So why wouldn't you have in the course of a long friendship discussed these mistakes in any kind of...
Michael Lynton 3:35 ↗
I mean, in my case, what happened as a result of the hack, which came out of the mistake I made, it was really painful. It hurt a lot of people at Sony, in my family, me. And I vaguely in the back of my mind, although I didn't really understand what happened entirely until I explored it, I felt responsible and I felt embarrassed. I felt a sense of shame about it. And so, it was just one of those things which felt icky and I didn't want to go near it. And Josh is 100% right. Whenever, not just Josh but anybody would raise it, I just looked away. You know, to this day I've never looked at my Wikipedia page.
Josh Lieb 4:23 ↗
Still, even after?
Michael Lynton 4:25 ↗
There are also, I think, different types of mistakes. There are the kind of mistakes we make, you know, you order the wrong thing at dinner, you forget someone's name, and sure, you talk about those. And then I think we've all experienced a lot of the humble brag mistakes. So I'll just tell one quick story. I was at our friend Gary Ginsburg's house, I think, or maybe it was yours, I can't remember, for a fundraiser and Bradley Cooper was there and he had just come out with this new movie and I said to him, 'It's a beautiful movie and there's a scene in the middle of the movie and it was so powerful. I just couldn't take it and I left.' And he looked at me and said, 'You walked out of my movie.' And I was trying to tell him it was so powerful and what I had done. And that's like this is the humble brag story. Oh, was it Bradley Cooper? And like that. And you talk about those mistakes, but the ones that really lead to embarrassment and shame are experiences people just don't go there. And in both of our cases, we had done things that were really shameful, we thought, and were unwilling to discuss them even with our closest friends or family, and just parked it and suppressed it. And those are the types of mistakes that we were most curious about and that we wanted to discuss in the book.
Malcolm Gladwell 5:29 ↗
We're going to—I want to get in a little bit to the mistakes that you're referring to, but there's a couple of interesting questions I want to start with. One is, what do you mean by a mistake?
Michael Lynton 5:42 ↗
Well, what we try and distinguish a mistake from is failure. So, a failure, which I would argue not most people don't get a chance to have a failure. A failure is when people come together, you analyze a situation and you make a decision that has ambition to it and for whatever reason it doesn't work out.
Josh Lieb 6:04 ↗
A mistake is completely different. A mistake is something you do in the moment. It's typically charged by your emotions in that moment. It doesn't take any analysis or very little at best and bad things happen as a result. And so that's the distinction we make and everybody makes mistakes and everybody makes mistakes all day long.
Malcolm Gladwell 6:26 ↗
You know what it reminds me of? Criminologists have this distinction they make between two kinds of violence. Instrumental violence is violence in the course of some other aim. I'm trying to rob you, right? Struggle, I shoot you. I rob a bank. I want to rob a bank and I end up shooting one of the guards. That's instrumental violence. And then it's what they call expressive violence, which is violence in the spur of the moment. We're having an argument.
Josh Lieb 6:52 ↗
Crime of passion.
Malcolm Gladwell 6:53 ↗
Boom. Crime of passion. And it strikes me that there's a similarity, not a perfect overlap, but that's valid. Talking about the difference between instrumental decisions and expressive decisions.
Josh Lieb 7:02 ↗
Yeah, very much so.
Malcolm Gladwell 7:04 ↗
And the criminologists say that we always assume that crime is instrumental and we forget that actually it's almost always expressive. And I wonder whether we are somehow—are we more comfortable with talking about failure than we are about talking about mistakes.
Josh Lieb 7:22 ↗
I think we are, partly because failure and success are siblings, right? They have much more in common with each other than failure and mistake. And I think that's one of the things where we really focus on the book. And we think of those two things as being synonymous. But both success and failure, as Michael said, you come out, you have a group of people, you have a plan, it's ambitious, and the only really difference between those two things is the outcome. Mistakes are totally different. And so I think when people talk about success and failure, it feels pretty good. Like there's something good that generally comes out of you. Even if you fail, like you're trying to do a big experiment, you don't find the compound that you hope to find, but you find some other synthetic material and what do you know? You have Post-its. It's awesome. They're sticky, but they don't leave any residue. And we like telling those stories because there's a happy ending and it's a little bit, you know, the hero's journey. Like you're out there, you're doing it. You overcome, you know, obstacle after obstacle. It's Odysseus. And that's very appealing. And that appeals to our American psyche. And it's very conforming I think with our view of ambition and how we realize it.
Michael Lynton 8:22 ↗
Yeah. And the other thing with a failure, you share the blame. I mean typically you're doing something with other people. Mistakes you're pretty much on your own and you have to take responsibility for it on your own.
Malcolm Gladwell 8:33 ↗
So you guys set out to write a book where you would first of all tell the story of your own individual what you felt to be your signature mistake.
Josh Lieb 8:42 ↗
We wrote a bunch of different mistakes and then we settled on the ones that we thought were most impactful.
Malcolm Gladwell 8:46 ↗
And then you went out and you collected a whole series of other people's stories of theirs. How did you—the list of people you go and talk to is quite fascinating. Tell me how did you go about finding people who were—if talking about mistakes is as difficult as you say it is. How did you manage to convince so many people to talk about them?
Michael Lynton 9:07 ↗
That's a good question. Well, many of the people, or some of the people, we knew, yourself included. And I don't know, there were a couple of people I remember calling up and saying, 'Would you care to do this?' And on one or two occasions they just outright said no. And there was one or two people said, 'Let me think about it,' and they came back to me and said, 'No, I have no interest in doing that,' or 'I thought about it, I don't want to do it.' But that actually wasn't much of a hurdle. Frankly, most people said, 'Okay, fine. I'll be willing to do that.' And then when we started the process, many of them actually didn't know what the mistake was until we were sitting down with them and we said, 'Okay, tell us what the mistake was.' And then they all had a mistake. They all had something that they really wanted to get off their chest.
Josh Lieb 9:54 ↗
Then the selection process was a mixture of people we knew. And then there were a few people we didn't know and we wanted to sort of explore certain themes and we were successful in finding some people who could help us with those themes, but not entirely.
Malcolm Gladwell 10:06 ↗
Yeah. And you enlisted the help of a psychologist.
Josh Lieb 10:11 ↗
Yeah, we did. We were really lucky.
Malcolm Gladwell 10:13 ↗
What did she—how did she assist you in this process?
Josh Lieb 10:16 ↗
She was awesome. It's a woman named Allison Papadakas. She's a professor of psychology at Hopkins. And when we started this process, we really, as Michael said, we started analyzing our own mistakes and got into it. And we began to develop a whole series of thesis and ideas and they were genius to state the obvious. And then shockingly when confronted with the academic literature not all of them withstood the validity that we had hoped. So her role really was a couple things. One was to sit with us initially and help us unpack our own mistakes, go deeper and deeper and deeper, get to what we thought was the underlying schema or root cause. Help us with other people's. So she listened to the interviews we did with other people and help us understand those. And then in each case we tried to find some aspect of the academic literature which was applicable, which related to what we described as the schema, the underlying personality trait that often drives these mistakes, and she was terrific. And then she helped us translate because you don't want an academic book. That wasn't our intent. We're not academics. And at the same time, if we're too loose with it, we're really doing a disservice to the researchers who had put so much time into their work. And she helped us bridge that divide.
Malcolm Gladwell 11:26 ↗
You were—I was, you know, I will—I was one of the people interviewed for this.
Josh Lieb 11:31 ↗
We refer to them as subjects.
Malcolm Gladwell 11:32 ↗
Yeah, I was one of the subjects. And I will say candidly, I found—I had two observations about the experience. One was we had to do—we didn't—we had to do two calls, right?
Josh Lieb 11:44 ↗
Yep. Mhm.
Malcolm Gladwell 11:44 ↗
I actually found it, in a way I had not anticipated, to be quite upsetting and unnerving.
Josh Lieb 11:54 ↗
And the other thing—no, it's okay. I'm...
Malcolm Gladwell 11:57 ↗
Now the revenge begins. And I've been quietly plotting. No, the other observation I had was that I thought that you guys were very, very good interviewers.
Josh Lieb 12:10 ↗
Oh.
Malcolm Gladwell 12:11 ↗
And I thought that was really interesting. And I wondered whether the experience of having reviewed your own mistake in such kind of meticulous detail had somehow freed you up to ask questions of others in a—it was more than thoughtful. It was—I felt it was like...
Josh Lieb 12:37 ↗
I felt I was being worked over by Muhammad Ali.
Malcolm Gladwell 12:40 ↗
Wow.
Josh Lieb 12:41 ↗
Yeah. Look at that.
Michael Lynton 12:43 ↗
Yeah, that's very gracious of you. So look, I think your point is right though because as Michael alluded to, we went through this process alone for a while with Allison and we tried it out with each other and with her and we blew it repeatedly with each other. I mean...
Malcolm Gladwell 12:59 ↗
Michael blew it. What do you mean?
Josh Lieb 13:00 ↗
So, Michael would be telling me a story, not one that was in the book. There's a great story that Michael tells about how he blew up a deal.
Malcolm Gladwell 13:06 ↗
Oh, right.
Josh Lieb 13:07 ↗
You want to tell that story just quickly?
Michael Lynton 13:08 ↗
No, it was just—I'd worked forever. I was in book publishing at the time. We were about to buy a company that we'd worked months and months on. The final call came when I was with my kids. One of them was actually on my shoulders at a county fair and I was in a really bad mood. The kids were misbehaving and it was one more demand and I blew up and I said, 'No, we're not doing that.' And the whole thing went away. And of course, that was a mistake. We should have gone ahead and done it.
Josh Lieb 13:34 ↗
And then I would ask questions about like the deal structure or I would ask questions or make a comment about his parenting style and it was just the wrong way to do it. Like it was insensitive. It was ill-informed. Like you can keep going whatever word ill applies to. And Michael's like, 'What are you talking about? That's not right.' And I was upsetting him.
Michael Lynton 13:54 ↗
Right. And so exactly to your point Malcolm, we had to learn how to do this. And I think part of what we try to talk about in the book is apply those lessons and lay them out as clearly as we can because it was a result of our misadventures and trying to understand other people's mistakes. So you're generous to say what you thought. Look, part of the risk for us, and you handled it really well, was we're not psychologists, and we were asking people to talk about something which was incredibly vulnerable and painful. And there were definitely moments where it felt very uncomfortable. And I remember, you know, after your conversations, Michael and I talked about a bunch, we talked about with Allison, and hopefully, you know, in between those interviews, we were expressing to you how grateful we were that you were as open as you were and as willing to talk about your family and your past. And that's what made this book from our perspective so meaningful that people were willing to trust us and then ultimately trust the readers with things which were deeply personal.
Malcolm Gladwell 14:49 ↗
So I thought it would be really interesting if we replicate this and Michael tells the story of his mistake but I'd like you Josh to be the interlocutor. I'm going to be silent. The two of you tell the story of Michael's mistake.
Josh Lieb 15:08 ↗
Okay. Let me just start. Michael, you did something which was so bone dumb. How could you have done it? I'm sorry. Let me try that again. I don't know. Let me try that again. Was that not what you had in mind?
Michael Lynton 15:16 ↗
No.
Josh Lieb 15:17 ↗
No. Okay.
Michael Lynton 15:18 ↗
So, how to start this? I'd been at the studio at the time for about 10 years. We had it pretty much...
Josh Lieb 15:26 ↗
Studio.
Michael Lynton 15:27 ↗
Sony.
Josh Lieb 15:28 ↗
Sony.
Michael Lynton 15:28 ↗
You were president of Sony.
Josh Lieb 15:30 ↗
I ran Sony Entertainment, which was...
Michael Lynton 15:32 ↗
I think the title is CEO.
Josh Lieb 15:34 ↗
CEO. Whatever. It was the studio and the music company. But at the studio, we had finally gotten it sorted and it was running pretty well. And I had been, you know, sort of the grown-up in the room, so to speak, for a long time. I was actually the suit. Nobody else wore a suit in it.
Malcolm Gladwell 15:50 ↗
So, just quickly describe the process for greenlighting a movie. How did that work?
Michael Lynton 15:54 ↗
What happened was, you know, it went through the development process and at the time we decided whether or not to make the movie. It had been budgeted and you brought a group of people around a table and you spend a couple of hours deliberating whether or not to make it. And there were finance people, marketing people, creative people.
Josh Lieb 16:10 ↗
And then when there's huge energy and drive, does that process apply or do you do something different? Like imagine Seth Rogen wanted to make a movie and he's the hottest thing in the movie business.
Michael Lynton 16:20 ↗
We stuck to that process regardless.
Josh Lieb 16:22 ↗
And did you in this case?
Michael Lynton 16:23 ↗
No, in this case this was a one-off.
Josh Lieb 16:27 ↗
Okay. So what happened?
Michael Lynton 16:28 ↗
So, in this particular instance, we had made a bunch of R-rated movies with Seth that had worked out. He was also making movies with Universal at the time. So, he had two places to go to. And he delivered a script to us which was called The Interview. It was about these two hapless journalists that go off to North Korea to interview and then were under the guidance of the CIA when they then assassinate Kim Jong-un. And he was putting a lot of pressure on us to make a decision quickly and everybody at the studio at the time wanted to make that movie because it wasn't expensive and we'd had a lot of success.
Josh Lieb 17:03 ↗
And did you decide on the spot or did you go through your normal process?
Michael Lynton 17:05 ↗
We did not go through our normal process but I had in the back of my head a reservation that I couldn't put my finger on. So I...
Josh Lieb 17:12 ↗
But before we get there, so you're in the room.
Michael Lynton 17:14 ↗
Yeah.
Josh Lieb 17:14 ↗
And they were like Seth Rogen and James Franco.
Michael Lynton 17:17 ↗
Let me back it up. So before we were in the room, we said, 'Let's have a read-through.'
Josh Lieb 17:21 ↗
Right. That's what I mean. Yeah. The read room.
Michael Lynton 17:22 ↗
So, we do the read-through, everybody shows up, all the creatives, all the talent. Again, I'm the only guy in the room with the suit and they, you know, Franco and Rogen are getting high before and everybody's laughing their heads off and it's obviously incredibly funny. And then it's over, meaning the read-through is over.
Josh Lieb 17:40 ↗
And what do you decide?
Michael Lynton 17:41 ↗
I jump up and in that everybody says, 'Let's do it.' And I look around and I say, 'Yeah, let's do it.'
Josh Lieb 17:47 ↗
Okay. So, now, so that process that I described before, that was the first time it just went away.
Michael Lynton 17:52 ↗
Okay. So now we say we've got super successful CEO designs a great process. Sony was very successful under your watch. And now that emotion of being in the room, you're sort of the insider outsider.
Josh Lieb 18:04 ↗
Yeah. Go back in time. Was there a moment in your life previously where you thought to yourself, I really want to be part of that crowd?
Michael Lynton 18:12 ↗
Well, I sort of always had that feeling, right, all my life. And it was really true when I got to Hollywood because I was not a Hollywood guy. But if I think about when it really started, it started because when I was eight or nine, my parents moved us from Westchester to the Netherlands. Bang in the middle of just as the school year started. And of course, my sister and I, we didn't speak any Dutch. And I was a very lonely kid for a couple years, you know, and I really didn't feel included in anything. And the friends that I did have, which I still have, were the nerdiest of the nerdy kids. And I wanted desperately to be with the cooler kids around. And that just wasn't available to me.
Josh Lieb 18:55 ↗
You taught me a great expression about Hollywood, which is there's always another velvet rope.
Michael Lynton 19:00 ↗
There is.
Josh Lieb 19:00 ↗
What does that mean? And give us an anecdote about, for example, George Clooney.
Michael Lynton 19:04 ↗
Well, no, I'll give you the perfect example of it. So, we made a movie with the band One Direction. We had a party for it afterwards. My kids were there. They were smaller at the time. I have three daughters. They're now in their late 20s, early 30s, but at the time they were, I don't know, 12, 11. And they were big One Direction fans. And we threw a party and it was at a restaurant and the restaurant had a balcony and everybody was down in the bottom of the restaurant and I was upstairs in the balcony with the VIP, so to speak. And at the end of the balcony, there was a little door and a big guy in front of the door. And I couldn't find the band anywhere. And I was desperate for my kids—not desperate, but I wanted my kids to meet the guys. And I walk up to the little door and I said, 'What's behind there?' And this big guy said, 'The band.' And I said, 'Can I go in there?' And he said, 'No.' And I said, 'But this is, you know, we're paying for this.' He said, 'Doesn't matter. You can't get in there.' That's another velvet rope. And that's the way that Hollywood works.
Josh Lieb 19:59 ↗
That's the way life works, actually. But it certainly works that way in Hollywood.
Malcolm Gladwell 20:02 ↗
So if I had to summarize, super successful career, great run at Sony. In a moment, you make a decision that you regret. But to understand why you made that decision. It wasn't about Seth Rogen. It wasn't about the North Koreans. It was about your own schema of what it feels like to be always a little bit on the outside looking in. And at that very moment, you were tired of it and you made a decision so you'd be part of the group. Is that a fair?
Michael Lynton 20:28 ↗
That sounds right. That sounds right. That would accurately describe how I was feeling right in that moment.
Josh Lieb 20:33 ↗
How do we do, Malcolm?
Malcolm Gladwell 20:35 ↗
Pretty good.
Josh Lieb 20:36 ↗
I mean, not when—normally I do this over the course of a couple hours. So yeah, that's the abbreviated version.
Malcolm Gladwell 20:42 ↗
So the movie is made and it results in retaliation by the state of North Korea.
Michael Lynton 20:49 ↗
Yep.
Malcolm Gladwell 20:50 ↗
And they bring Sony to its knees. Hack.
Michael Lynton 20:55 ↗
Yep. They're very good at what they do.
Malcolm Gladwell 20:57 ↗
Hack every server.
Michael Lynton 20:59 ↗
Yeah.
Malcolm Gladwell 21:00 ↗
Leak all the emails.
Michael Lynton 21:01 ↗
Leak all the emails.

118 more exchanges in this transcript

Sign in free to read the rest of this interview. No card required.

Sign in to read the full transcript

Cite this transcript

APA, MLA, BibTeX
APA

Lynton, M. (2026, March 10). Malcolm Gladwell, Michael Lynton and Joshua Steiner in Conversation: From Mistakes to Meaning [Interview transcript]. The 92nd Street Y, New York. CEOInterviews.AI. https://ceointerviews.ai/interview/762402/

MLA

Michael Lynton. "Malcolm Gladwell, Michael Lynton and Joshua Steiner in Conversation: From Mistakes to Meaning." The 92nd Street Y, New York, 10 Mar. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/762402/.

BibTeX
@misc{lynton2026_762402,
  author       = {Michael Lynton},
  title        = {Malcolm Gladwell, Michael Lynton and Joshua Steiner in Conversation: From Mistakes to Meaning},
  howpublished = {Interview transcript, The 92nd Street Y, New York. CEOInterviews.AI},
  year         = {2026},
  month        = {mar},
  url          = {https://ceointerviews.ai/interview/762402/},
  note         = {Speaker-attributed transcript with timestamps}
}