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Andrew Ross Sorkin
I always say you can never actually blame the guest. You are like an animal trainer. It is your job to make the elephant dance and you can never blame the elephant. And that is the responsibility of the host.
Adam Grant
Hey everyone, it's Adam Graham. Welcome back to Rethinking My Podcast with TED on the Science of what Makes Us Tick. I'm an organizational psychologist and I'm taking you inside the minds of fascinating people to explore new thoughts and new ways of thinking. My guest today is Andrew Ross Sorkin, my favorite business journalist. He writes for the New York Times Dealbook, which he founded, and co anchors Squawkbox on cnbc. Over the years, Andrew and I have had some fascinating conversations about the psychology that drives some of the most powerful people of our time. And he's equally interested in the financial decision makers who lived almost a century ago during the stock market crash of 1929. So interested in fact that he wrote a riveting new book about it called 1929. Before we dig into that, I wanted to talk to him about interviewing because he's a world class interviewer. You introduced me last year to what has become my favorite metaphor for an interview. That becomes a great conversation. You said, it's like a tennis match. Talk to me about that and how you landed at this metaphor.
Andrew Ross Sorkin
So, first of all, I love tennis and I love watching a long rally. Just watch the U.S. open. And you know, people always say to me, who are you rooting for? And I always say, I'm rooting for a long, long match. That's what I want. And I think that's what everybody wants. And to me, a great conversation is that you don't really want to see one person acing the other person over and over again. There's very little learn from it. It's not particularly entertaining. There's just no excitement about it. And by the way, that doesn't mean you're not gonna hit the ball hard. It just means that two things, you actually want the other person to return the ball. Like it's important that the other person can return the ball. And sometimes you'll place the ball in the corner to see if they can run. And by the way, sometimes they're gonna place the ball in the corner to see if you can run. But it just makes for a much more interesting dialogue.
Adam Grant
It was an important lesson as somebody who early on used to work too hard to please the guest and then realized, I'm not here for the. The guest and I are here for the audience.
Andrew Ross Sorkin
Bingo. Bingo was his name. O.
Adam Grant
You must think about this all the time, Andrew, because anytime you have someone on TV or on stage, you have to deprioritize your relationship with them in service of all the viewers, Right?
Andrew Ross Sorkin
So, yes, but one of the things that I think is, and you've tried to do it now with me, I think it's incumbent upon me to convince the guest that it's actually in their interest to serve the audience.
Adam Grant
Oh, I like this. That removes the conflict.
Andrew Ross Sorkin
If you can. Doesn't always work.
Adam Grant
But some guests are naturally both good at that and motivated to do it. And they show up and you think, oh, this person already realized that we're trying to deliver a great live performance.
Andrew Ross Sorkin
Right.
Adam Grant
What do you do when guests don't get.
Andrew Ross Sorkin
Depends what environment we're in. So if we're on television, we go to commercial.
Adam Grant
So next time you call a commercial break on me, I'll know what you're doing.
Andrew Ross Sorkin
If it's on a stage. More complicated. So it is on you to figure out how through hook or crook, through carrot or stick, through. I don't know what that you are going to make it work.
Adam Grant
I think you're creating unrealistic expectations of the host. You can't make every elephant dance.
Andrew Ross Sorkin
But that's the gig. That's the gig.
Adam Grant
Yeah, but Andrew, doesn't that mean that sometimes you just. You pick the wrong elephant?
Andrew Ross Sorkin
Yes, that is true. You can sometimes pick the wrong elephant. But then again, that's on you for picking the wrong elephant. So it always comes back to it's always my fault in the end.
Adam Grant
Is this why you never feel like you've succeeded?
Andrew Ross Sorkin
Yes.
Adam Grant
I've seen you do world class interviews, and at best your reaction is, I thought it was pretty good in parts.
Andrew Ross Sorkin
Grading on a curve.
Adam Grant
Always. I try to only curve upward, never downward. Okay, so this actually speaks to something I wanted to ask you about, which is, please. I try not to use superlatives unless they're both specific and honest. So this one will be both. I don't think there's a better interviewer alive than you.
Andrew Ross Sorkin
Oh, my God.
Adam Grant
So it's a lot of pressure to interview you, and I want to get your advice. How should I do this?
Andrew Ross Sorkin
So, first of all, thank you for saying that. And that's ridiculous. First of all.
Adam Grant
That's very Canadian of you.
Andrew Ross Sorkin
But you know me, Adam, I am not Canadian. I'm a very anxious human. What is it to prepare for an interview? I think. Look, all I'm trying to do when I prepare for an interview is, is figure out where the fault lines are. That's literally what I'm always trying to do. I'm trying to figure out what is the issue, what is the thing that drives this person. I desperately try to put myself in their shoes. I wanna know where all the speed bumps are before the interview. I always find that that's actually super important to know where the speed bumps are. Because then I can know how we can either work around the speed bumps or how we can actually go over them together.
Adam Grant
What are examples of speed bumps?
Andrew Ross Sorkin
Tough questions. Something that they've done where maybe they've made a mistake or they didn't do something. Right. Oftentimes those can be great educations, actually, for the audience, because there's oftentimes a lesson embedded in the mistake. And by the way, I think when the question's posited like that, the guest feels a lot more comfortable talking about what that mistake was, because they do know there was a personal lesson for themselves, sometimes asking a guest about a critique of them or a critique of something they've done. So one thing that I've always found can be helpful in that context is to read a critical quote to them, and it could be about them. And the reason to approach the question that way is two reasons. One is it takes it out of being your critique.
Adam Grant
Right.
Andrew Ross Sorkin
It's somebody else's critique. And two is the truth is because most people are vain enough to actually read about themselves, they've probably read the quote before. They've probably thought about the quote a lot before. It might even pain them, the quote, but they have an answer for the quote. So in a way, even though you may have never told them that you plan to ask the question, it's not out of the blue. Look, the other thing that I feel like I often do ahead of a difficult question is I say, this is a difficult question, or here's a complicated question, and it's just another way of trying to meet people where they are and acknowledge to them that I understand that this is not easy and that we're going to try to grapple with this in some way together.
Adam Grant
This is so interesting. So I love this approach of saying, hey, here's a critique of you respond to it. I think you're right. It takes you out of sort of the attack position and makes you almost a neutral moderator, arbiter, maybe even a sympathetic one, because you're giving them a chance to counter whatever the critique has been. I wonder, is there a boundary condition on that? Which is to say you can't do that if you're doing investigative journalism or some kind of interrogation. It only applies to the kinds of interviews that you and I both do, which. Which are. I'm fundamentally here because I think there's something to learn from this person, and I want to make sure that the audience doesn't miss out on their teaching.
Andrew Ross Sorkin
Oh, totally. So there's a couple of different Kinds of interviews contextually, that I do. But the truth is actually that oftentimes the same kind of approach can work. I don't think that it has to necessarily always feel like a full on interrogation. And by the way, sometimes there's an ordering of your questions so that you're going from one thing to another, where you're trying to lead to a place where you know, okay, now it's going to be a little more complicated for the other person to slip out, if you will, of actually answering the question because they've answered three other questions in a very specific way.
Adam Grant
In psychology that's called the four walls technique.
Andrew Ross Sorkin
See, you know all of these techniques. I, I've never really studied this.
Adam Grant
I'm just naming it.
Andrew Ross Sorkin
You're naming it. I just. This is.
Adam Grant
You described it. No, I mean if you picture it vis. Right. You're getting them to answer a first question which creates one wall that they can't break through and then a second question and eventually they're in a box where.
Andrew Ross Sorkin
Yes, you've cornered them.
Adam Grant
Yeah, exactly.
Andrew Ross Sorkin
Yes. And sometimes you have to corner people if you're trying to get to a particular kind of truth. That's very true too. But again, I think the context, it depends a little bit on what the setup is. Some people have sort of a long list of questions. I don't usually do that. I sort of usually have like a couple of points of places I want to go as if I'm the pilot of a plane that knows I am starting at JFK and I'm going to end at lax. And invariably, I know we're probably going to have to make a pit stop in o' Hare and Denver and somewhere else, but the weather's going to change along the way and so we're probably going to shift the plan. But if you're trying to do the four wall approach that you're talking about, then you have to be very exacting.
Adam Grant
It's interesting because I think both my best and worst conversations are the ones where I have the fewest notes going in.
Andrew Ross Sorkin
Your best and worst are the.
Adam Grant
Yeah, both extremes. And it really depends on are they. A good dancing elephant with great dancing elephants, no notes is ideal because we both end up improvising and it's. It's an unexpectedly delightful conversation. And that depends not just on them, but on our relationship and how well I know them.
Andrew Ross Sorkin
Right.
Adam Grant
But some of the worst ones also are when I think I know what's gonna make the person interesting. And I've underprepared as a Result. And it just doesn't land.
Andrew Ross Sorkin
Okay, but aren't you most proud of the interview where you know that the person you're interviewing is a tough interview, they're an elephant that doesn't wanna dance, and that somehow you've reached them, somehow you found a way to meet them where they are and that they've chosen to dance.
Adam Grant
I look forward to that day when it happens. Who has. Who has been that for you?
Andrew Ross Sorkin
Oh, so many different people. You know, a couple years ago, I did an interview with Elon Musk that went.
Adam Grant
Is this the one where he told Bob Iger to F off?
Andrew Ross Sorkin
Yes. Don't advertise. You don't want them to advertise?
Adam Grant
No.
Andrew Ross Sorkin
What do you mean?
Adam Grant
If somebody's gonna try to blackmail me.
Andrew Ross Sorkin
With advertising, blackmail me with money, go yourself. But go yourself. Is that clear? I hope it is. Well, let me ask you then. Look, Elon Musk is a dancer. He likes to dance on the stage in many ways. But at that point in the interview, which was actually quite early in the interview, it could have gone off the rails. And I could tell that this could spiral in all sorts of ways. And so to me, in that moment, it was on me to figure out a way to meet him, where he was. And so we started really talking about where all of this comes from in him. Meaning instead of talking about Tesla or SpaceX or all of the things that I imagine he thought we were going to talk about, and frankly, that I thought we were going to talk about, at least early on in the conversation, I completely switched gears in hopes that, okay, I could sense he was in this place. And I thought, okay, maybe we can really do something interesting here, talk about what that place feels like. And then once we could go deep there, then we could go to all these other places afterwards, and happily that happened. So that's an example.
Adam Grant
That's a really good example.
Andrew Ross Sorkin
So can I just ask you a question for a second?
Adam Grant
Whose show do you think this is here?
Andrew Ross Sorkin
The mic is yours. This is your show. The distinction between an interview like this in a podcast or on a stage in the media and a job interview, you might say to yourself, they might seem like totally different things, but I often find that a lot of the same things that I try to do in an interview on TV or even in a podcast are almost identical to the things I'm trying to do in a job interview when I'm thinking about hiring somebody. Because what I'm trying to do in my own way is to meet them where they are. And figure out sort of how far, again, where can I place the ball on the court? Can they actually hit the ball? Are they capable of doing this in a job interview? I'm hoping they hit the ball back.
Adam Grant
Oh, that's so interesting. I never thought about it that way. Yes, I think that's right. I think ineffective interviewers approach it like an interrogation. And what they're trying to do is set the candidate up to fail or stumble. And sometimes that's because they really enjoy watching you squirm at an impossible brain teaser. And sometimes it's because they think that their job is just to grill the person and that will show what they're really made of. And if the job you're hiring for requires performance under extreme pressure, that makes sense. The reality is most job performance doesn't. And so what you want to do is create the conditions that best simulate what the actual work is going to involve. And I think you're right. I think that this kind of conversation, a good tennis match, is the ideal with that because you're both trying to give the person a chance to show their strengths. But you're also, you're not just hitting them lobster, you're hitting a cross court shot or a drop shot that you're hoping they're gonna have to sprint or dive to get. And then if they do, you can say, well, totally.
Andrew Ross Sorkin
Oh, I don't know if this is a tangent. I do do one thing that you should just know that I do. It's just an easy, silly thing that anybody can do. If I'm interviewing a CEO or a politician, I will oftentimes write their name and, or their company or institution or affiliation and write the word controversy into Google just again to find the speed bump so that I know where all of the sort of different component parts are around that person.
Adam Grant
Have you done that on yourself to prepare for the speed bumps that other people are going to throw at you?
Andrew Ross Sorkin
I haven't done that. The only thing I did do once is I did a thing on ChatGPT. Completely narcissistic and egomaniacal thing to do, which is to ask ChatGPT to psychoanalyze you and to tell you the most, give it to the most critical feedback you can, and I'll say, don't be nice, tell me everything that I'm doing wrong. And I have to say it was pretty impressive, a little depressing, and I thought it got me. Now what I don't know is whether it's like a horoscope or a fortune cookie and that anybody who reads these things would feel the same way about themselves. But I thought it was pretty good.
Adam Grant
There's a truthiness in it that it feels real. The term for that would be the Forer effect or the Barnum effect. Yes. So did you learn anything from it that you then subsequently validated that you hadn't previously known about yourself?
Andrew Ross Sorkin
No. I am narcissistic enough to know all of the problems. I just don't know how to fix them all.
Adam Grant
Wait, I'm sorry, Andrew. No, no, no. Well, okay, maybe, maybe I'm thinking about the wrong kind of narcissism. But if you were a grandiose narcissist, you wouldn't know most of the problems because you would be shielding your fragile ego from them. But maybe, maybe you're describing a vulnerable narcissist who is constantly afraid of all of your flaws.
Andrew Ross Sorkin
That. Or maybe it's like a masochistic narcissist.
Adam Grant
Self hating narcissist. That's a new one, by the way. I think it's uncharitable in the same way that you're uncharitable about your great interviews of you to call this narcissistic. Because a big part of wanting to know what your weaknesses are is wanting to show up as a better version of you for everyone in your life and everyone who engages with your work.
Andrew Ross Sorkin
Yes, but the constant effort. And I'm one of these people and I think you're like this too, but hopefully not to the extent I am because I don't think it's healthy.
Adam Grant
I.
Andrew Ross Sorkin
It's a constant sense of trying to make everything better, of trying to fix it, to improve it at every, you know, every little thing, whether it's a health thing, working out thing, food thing, family balance thing, writing quality thing, research. I mean, I'm always in some terrible way trying to like over optimize the situation to make it better. And there are people that I know who I just think are comfortable with who they are and they feel that they're enough.
Adam Grant
Yeah.
Andrew Ross Sorkin
And that is. That to me sounds like a really great place to be.
Adam Grant
It does. I've tried to become more of that person over time. So what you're describing is not narcissism, but perfectionism, maybe. And I think that's, that's fair. I mean, there are multiple motivations for perfectionism though. One, you know, one is very egotistical. You know, I want to look good and I want to feel good about myself and there's self esteem and an image wrapped up in that, but there, there is also the pro social component of it, which is I don't want to let other people down and I want to make the most valuable contribution I can. And I think if we're being honest with ourselves, it's probably a mix of those two things that fuels it.
Andrew Ross Sorkin
I do think it's a mix of those two things, ultimately.
Adam Grant
So we've talked over the years about the front row seat you have to the psychology of powerful people. What do you know about them that the rest of the world doesn't? What do they show you that we can't see?
Andrew Ross Sorkin
I think the truth is that most people who've had what I describe as shoot the moon success, the ones that we read about, see on tv, see headlines about, despite all of the success, still feel like they have something to prove, that there's some underlying almost insecurity, hopefully a healthy insecurity, not an unhealthy insecurity, because insecurity can cut both ways, but some kind of insecurity that is propelling them forward, that is driving them to want to prove to somebody. Maybe it's their mother, maybe it's their spouse, maybe it's somebody in high school who told them that they couldn't do it. Even the ones who appear to have scaled themselves to the absolute top of the mountain. And you think to yourself, okay, I got to the top of the mountain, now I'm just going to ski down. And yet they don't ski down. They keep looking up for something else. And what is that? And I think ultimately, as I said, I think there's an. It sounds so crazy to say that people of that sort of level of success could ever feel insecure at all, but I think ultimately they do. You know, Oprah Winfrey famously has talked about how when people finish having a conversation with her, they always ask her the same question. Was it good? Did I do okay? It's the most human emotion, even, by the way, the people who seem the most narcissistic and confident oftentimes are the least.
Adam Grant
I do feel like I've encountered a subset of them who abandon most of the insecurity. They still hang on to the normal human. You know, I don't want to look like I have food in my teeth. I don't want to say something that makes me sound like an idiot.
Andrew Ross Sorkin
Right?
Adam Grant
But don't worry a lot about how they're perceived. But still, they still keep looking for the next mountain because they realize I can do more, I can challenge myself more, and I enjoy growth I can contribute more and I like helping other people. And also with that comes, you know, status and relationships that I value. And so it seems like a win.
Andrew Ross Sorkin
So you think you've seen a transformation in some people who've started without success, got to success and then actually did have that confidence? Yeah, most of the people that I know who've gone from the bottom of the mountain to the top of the mountain, they're the same at the bottom of the mountain as they are at the top. The one difference is actually about something slightly different, which is curiosity and curiosity about others. I found actually that some of the most successful people in the world are the most curious, almost invariably curious, and that one of the things that does happen with great success is that they not always, but many, become less curious. And I don't know if that's a function of narcissism or sort of inward looking. I don't know if that's a function of you get into a situation where you have yes men around you sort of all the time and so you don't know any better. You can really put yourself into a bubble. And I think the money can sometimes do that. But the people that I sort of adore the most, especially the ones who've had great success, still ask the most curious and even mundane questions.
Adam Grant
Yeah. I think this is interesting. It makes me wonder about the following, which is I think you're right about some of the contributing factors to why curiosity wanes. And it does go against the general trend that I think you've observed and I've seen in the research, which is more often power reveals as opposed to power corrupts. It amplifies the pre existing traits as opposed to transforming them. But this is one that you think does change. And I've seen it to some extent too. I wonder if another factor is, and this is maybe being overly charitable to some of these people, but they're in the position of being asked questions all the time. And it's a little different than having yes men and women around you. They get in the habit of, oh, my value added is the answers I offer, not the questions I ask.
Andrew Ross Sorkin
I think you're 100% right. And I would say that's not just a sympathetic or empathetic view. I think that it's actually the accurate view because I do think a lot of these people, especially when they get to a certain level, you know, questions are coming at them left and right and that's become sort of the default position that they get used to being in.
Adam Grant
Yeah.
Andrew Ross Sorkin
And So I don't know if their curiosity has dissipated per se, but maybe it's just not expressed as much or in the same way. It's latent they're expecting you to ask the question.
Adam Grant
Yeah, but I mean, that's a violation of, you know, basic norms of politeness and respect.
Andrew Ross Sorkin
Yes, you're in the podcast business, so we gotta ask questions. More than that, it's not. It's not the podcast business. It's the business of life. Life is about, hopefully learning about other people.
Adam Grant
Yep, I think that's right.
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Adam Grant
Okay, so Andrew, you have a new book.
Andrew Ross Sorkin
Yes.
Adam Grant
That we need to talk about. It's called 1929. I think it's possibly the clearest book title ever written. This is going to be about the biggest stock market crash in history.
Andrew Ross Sorkin
Yes. This was for me, trying to go back in history and try to understand what happened really with the first, most infamous financial crash in history. And not just what happened. I think we all know something bad happened, the stock market fell. But in the same way, we're talking about curiosity and people at the top, really trying to understand who the people were who the characters that populated what was a shocking and fabulous and fascinating drama, really, and what drove them both before the crash to make the mistakes that they made. You know, the conversations they're having with their spouse and the slights from one person to a next that might affect someone to try to drive, to prove themselves or to take a risk. And then all the efforts that were made after the actual crash itself that frankly didn't work and made things in many cases worse. And so the challenge for me was in finding all of the information, but also in trying to put myself in their shoes. That's a lot of what I was trying to do throughout the whole process was trying to figure out, okay, what is motivating these people? What is the incentive for them? What is that insecurity that's driving them to do what they're doing?
Adam Grant
What changed the most for you in your perception of what caused either the crash or the failures to recover from the crash? Like, what did you end up rethinking the most?
Andrew Ross Sorkin
I think the thing that was for me the biggest revelation and so much of what we think is the American dream started. This is maybe a behavioral psychology thing, Adam. I think in a way started in the 1920s, which I don't think I appreciated going into this project at all. The whole sort of like, get rich quick idea was actually like a very 1920s idea. The idea of sort of business people and entrepreneurs and wealth as celebrity was actually a function of the 1920s. So all these people we're talking about today, Elon Musk, Jeff Bezos, all that, all that didn't happen before the 1920s. You know, before the 1920s, you know, Babe Ruth was on the COVID of magazines and Charles Lindbergh was on the COVID of magazines. But then all of a sudden, the main character of this book, a guy named Charlie Mitchell who runs a bank, is on the COVID of the magazines. And it's a very different idea. And then a separate issue, just about risk that people never really understand, sort of where the line is on risk, and are willing to take extraordinary risk. And everybody wants to win the lottery. Everybody wants to win the lottery. And it became, I think, acute in the 1920s.
Adam Grant
Okay, so reconcile that view with my naive understanding of the roots of the American dream. When I hear American Dream, I think about the Horatio Alger rags to riches stories of the mid-1800s. And following that, I think about the celebrity of Thomas Edison and JP Morgan and John Rockefeller. How do you square that circle?
Andrew Ross Sorkin
This happens, I think, when you get into both a period of inequality, but also a period of opportunity and excess. And that's what happened in the 1920s, where everybody all of a sudden had access to debt, to credit. So also, that's the other thing that happened, which I didn't know. I don't think I fully understood. You could go, literally buy stock with a dollar, and then the bank would give you the $10. And as long as everything was going up, it was like free money. And there were brokerages on the corner of the streets in New York, like, there's Starbucks. I mean, you could walk into a hotel and you could trade anywhere. And gambling became an American pastime. And I think in many ways, gambling is part of our pastime today.
Adam Grant
Wow. So what is the biggest lesson from 1929?
Andrew Ross Sorkin
That we haven't learned two things, and they're really hard. One is some semblance of humility, which is to say we're probably always going to have crashes. We're probably always going to have bubbles, and the bubbles are going to burst. And the goal probably isn't to eliminate the bubble completely. The goal is to make sure that the bubble doesn't get too far out of hand. But the problem, as you know, is when everybody's at the punch bowl and the party's rolling. Nobody really wants the party to end or to stop. And so how we as human beings almost self regulate ourselves I think is a super hard thing to do. The other lesson for me, which is almost antithetical to everything we've been talking about, is that for innovation to happen, you actually do need speculation. Speculation is the twin of innovation. Elon Musk could not have had success unless somebody was willing to speculate on him. And what looks like a speculation to one person can turn into a good investment for somebody else. And so how we sort of think about the two sides of that coin, again, I think it's super complicated, but I think there's a lot embedded in there.
Adam Grant
I think so too. It reminds me a little bit of Michel Gelfand's research on tight versus loose cultures. It tracks really closely with what you're describing, which is in a tight culture that has lots of regulation to try to prevent a collapse, you also end up squashing innovation.
Andrew Ross Sorkin
Right. And so how do you avoid that? Or do you just accept that it's part of the game? Especially when some people are getting, you know, stupidly wealthy doing it and other people are losing in the process. And that's the hardest part. I think about a lot of this.
Adam Grant
Yeah, I mean, I think in an ideal world we would have guardrails that minimize the downside losses. Right. So like securing banks is a, is a helpful step in that category.
Andrew Ross Sorkin
The one thing though that I think, and this goes to the sort of behavioral science of it, I actually don't write about this in the book. My grandfather, who's since passed away, was a messenger boy in October of 1929, and he was down there during the crash. And my grandfather, who lived till 92, never bought a share of stock of any stock his entire life after that. He really believed that like the stock market was this very dangerous place and it wasn't for like the common folk, by the way, big mistake. He used to buy bonds and all sorts of things. He would talk about this with the family. But it's so interesting to me that these moments in life can have such a scarring effect. And I think my grandfather was of a generation that had that, that were all scarred like that. And so I think about just sort of the psychological impact that these bubbles and the bursting of these bubbles can have.
Adam Grant
Well, that's the big question that I was thinking about when you said bubbles are inevitable is what do we do as individuals knowing that?
Andrew Ross Sorkin
Well, part of the psychological problem that my grandfather and other people experienced was that they didn't know.
Adam Grant
Right.
Andrew Ross Sorkin
It was like getting hit over the head with a two by four that they didn't see coming. They were blind to it and that's why it was so scarring. I think that the more people understand about how the system works that it can go up and down, that it's actually not all going up, that can be a little dangerous along the way. That to me, unto itself, just the information is power to some degree.
Adam Grant
Yep, yep, I think that's right. It's a question of managing expectations which then can lead to smart choices like diversifying portfolios, hopefully whatever else you might recommend. Yes, I like that. Hey, it's Adam Grant from ted's podcast Work Life and this episode is brought to you by ServiceNow. AI is only as powerful as the platform it's built into. That's why it's no surprise that more than 85% of the Fortune 500 companies use the ServiceNow AI platform. While other platforms duct tape tools together, ServiceNow seamlessly unifies people, data workflows and AI connecting every corner of your business. And with AI agents working together autonomously, anyone in any department can focus on the work that matters Most. Learn how ServiceNow puts AI to work for people@servicenow.com.
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Adam Grant
Okay. Do you have time for a lightning round?
Andrew Ross Sorkin
Yeah.
Adam Grant
What is the worst advice you see people get when it comes to either interviewing or being interviewed?
Andrew Ross Sorkin
The worst advice people get when they're being interviewed is to show up with these three points that they're supposed to repeat over and over and over again. But the best interviews, the ones that you like the most, are the ones where it feels like the person is actually grappling with the question. So for all of those folks out there who have PR people or lawyers or other people saying, show up with an index card with three things on it, listen to the question and try to answer the question. Now can you pivot at some point to try to make the three points you want to make? Yes, and you should. That's why you're doing it. But if you want to have credibility with the audience, you need to try to engage with the question.
Adam Grant
Who is at your dream dinner party alive or dead?
Andrew Ross Sorkin
Can I restructure the question?
Adam Grant
Yeah.
Andrew Ross Sorkin
For some reason I went to immediately like who's dead that you'd want to interview and my mind went to Michael Jackson.
Adam Grant
Wow.
Andrew Ross Sorkin
I can't even begin to think about how you could unpack that life and those decisions, how he felt throughout all of that, you know, what drove him throughout this whole life of his, how he thought about his impact. My goodness, I could go on and on.
Adam Grant
What's a hot take that you are excited to defend an unpopular opinion that you would like more people to hold?
Andrew Ross Sorkin
Money is not emotional armor.
Adam Grant
I believe that.
Andrew Ross Sorkin
I think that most people think it is.
Adam Grant
I think they are wrong and you are probably right. But I await evidence to change my mind.
Andrew Ross Sorkin
Oh, I'll give you one. But it's because I live in the morning TV business. I know people say like nothing good happens after midnight. I go with nothing good happens after 8:30.
Adam Grant
Is that why you always leave after dinner at conferences?
Andrew Ross Sorkin
I'm convinced. I don't think anything that interesting happens after 8:30.
Adam Grant
Except that sometimes that's when people let their guard down and relationships are built.
Andrew Ross Sorkin
That is true.
Adam Grant
I find that people are generally less stiff over the course of the day.
Andrew Ross Sorkin
So that's true. You can, you can learn a lot.
Adam Grant
A couple wrap up things, please. One is, I want to make sure we give you a chance to give me a bit of feedback on my hosting slash interviewing since we started there, I feel like we should end there. How did I do?
Andrew Ross Sorkin
Pretty great. But if I were to tell you you did terribly and it's your own podcast, how would that work? Well, I'd give you an A minus. That means there's always room for improvement.
Adam Grant
I'll take your A minus.
Andrew Ross Sorkin
What could you better? I wasn't sure going into this, but very happily where we were going to go, what we were going to talk about, what it could be. And I kind of enjoyed that. But maybe I would have given you more canned answers then if I knew more thematically would have I like thought about it more and then had a better answer for you. And sometimes you want a better answer and sometimes you don't want a better answer. So I don't know the answer.
Adam Grant
Well, this is the problem with your rare breed of elephant is that's exactly the trade off. I knew if I gave you an arc you would deliver it, but I also knew it would take fewer unexpected turns.
Andrew Ross Sorkin
If we did that right, we got the serendipity. It was good.
Adam Grant
Rethinking is hosted by me, Adam Grant. The show is produced by TED with Cosmic Standard. Our producer is Jessica Glaser. Our editor is Alejandra Salazar, our engineer is Asia Pilar Simpson, our technical director is Jacob Winick, and our fact checker is Paul Durbin. Our team includes Eliza Smith, Roxanne Hylash, Banbam Cheng, Julia Dickerson, Tansika Sung Manivan and Whitney Pennington Rogers. Original music by Hans Dale Su and Alison Layton Brown. I'm gonna pretend we're on squawk here.
Andrew Ross Sorkin
I don't know. There's no commercial break, but go for it.
Adam Grant
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Adam Grant
Hey, it's Adam Grant from Ted's podcast Work Life, and this episode is brought to you by ServiceNow. AI is only as powerful as the platform it's built into. That's why it's no surprise that more than 85% of the Fortune 500 companies use the ServiceNow AI platform. While other platforms duct tape tools together, ServiceNow seamlessly unifies people, data workflows and AI connecting every corner of your business. And with AI agents working together autonomously, anyone in any department can focus on the work that matters Most. Learn how ServiceNow puts AI to work for people@servicenow.com.
Sponsor/Advertisement Voice
This episode is brought to you by Capital One. Capital One's tech team isn't just talking about multi agentic AI. They already deployed one. It's called Chat Concierge and it's simplifying car shopping using self reflection and layered reasoning with live API checks. It doesn't just help buyers find a car they love, it helps schedule a test drive, get pre approved for financing and estimate trade in value. Advanced, intuitive and deployed. That's how they stack. That's technology at Capital One.
From: ReThinking with Adam Grant | Published: December 22, 2025
This episode features a conversation between organizational psychologist and host Adam Grant and renowned business journalist Andrew Ross Sorkin. They explore "the art of the interview," delving into the psychology and techniques behind great conversations both in media and in job interviews. The discussion extends from the nuances of hosting high-stakes interviews to Sorkin’s new book, 1929, which examines the personal forces behind the world’s most infamous financial crash. The episode is a masterclass in interviewing, curiosity, and understanding what drives high achievers, offering advice that is as practical for the boardroom as it is for broadcast.
Interview as a Tennis Match
"To me, a great conversation is that you don't really want to see one person acing the other person over and over again...it just makes for a much more interesting dialogue." (Andrew Ross Sorkin, 03:58)
Responsibility of the Host
"You are like an animal trainer...it is your job to make the elephant dance and you can never blame the elephant." (Andrew Ross Sorkin, 02:31)
Navigating Uncooperative Guests
"It is on you to figure out how... you are going to make it work." (Sorkin, 06:09)
Preparation Techniques
“I desperately try to put myself in their shoes. I wanna know where all the speed bumps are before the interview.” (Sorkin, 07:31)
Handling Difficult Topics
“I say, ‘this is a difficult question,’ or ‘here's a complicated question,’ and it's just another way of trying to meet people where they are and acknowledge to them that I understand that this is not easy.” (Sorkin, 09:08)
Types of Interviews and "Four Walls" Technique
“Sometimes you have to corner people if you're trying to get to a particular kind of truth.” (Sorkin, 11:47)
Improvisation vs. Over-preparation
“Some of the worst ones also are when I think I know what's gonna make the person interesting. And I've underprepared as a result, and it just doesn't land.” (Grant, 12:58)
“I could sense he was in this place...so we started really talking about where all of this comes from in him...and then once we could go deep there, then we could go to all these other places afterwards.” (Sorkin, 14:14)
Sorkin draws a direct parallel between media interviewing and job interviewing—both aim to create a give-and-take akin to his tennis metaphor:
"What I'm trying to do in my own way is to meet them where they are....In a job interview, I'm hoping they hit the ball back." (Sorkin, 15:18)
Adam Grant reflects that the most effective job interviews replicate the real working environment’s give-and-take, rather than pressure-cooker scenarios.
Research 'Controversy': Sorkin Googles "[Name] + controversy" before high-profile interviews to anticipate tough questions.
"It's just an easy, silly thing...just to find the speed bumps." (Sorkin, 17:10)
Self-analysis: Sorkin once asked ChatGPT to provide critical feedback about himself, finding value in self-awareness (with a nod to the "Forer/Barnum effect" of generalized feedback).
“I am narcissistic enough to know all of the problems. I just don't know how to fix them all.” (Sorkin, 18:45)
Perfectionism & Improvement: Sorkin and Grant discuss their drive for continual self-improvement—a double-edged sword of perfectionism.
"It's a constant sense of trying to make everything better, of trying to fix it..." (Sorkin, 19:49)
Sorkin observes that many high achievers are propelled by insecurities, regardless of their outward success:
“Despite all of the success, still feel like they have something to prove...even the ones who appear to have scaled themselves to the absolute top..." (Sorkin, 21:27)
Curiosity is often high in great leaders, but may wane as they accrue power and "answers" become expected of them rather than questions.
“Some of the most successful people in the world are the most curious...one of the things that does happen with great success is that they...become less curious.” (Sorkin, 23:51)
| Timestamp | Quote | Speaker | |-----------|-------|---------| | 02:31 | "You are like an animal trainer. It is your job to make the elephant dance and you can never blame the elephant." | Andrew Ross Sorkin | | 03:58 | "A great conversation is...a long, long match...you actually want the other person to return the ball." | Sorkin | | 05:07 | "...it's incumbent upon me to convince the guest that it's actually in their interest to serve the audience." | Sorkin | | 07:31 | "I desperately try to put myself in their shoes. I wanna know where all the speed bumps are before the interview." | Sorkin | | 09:08 | "...this is a difficult question, or here's a complicated question, and it's just another way of trying to meet people where they are..." | Sorkin | | 11:47 | "Sometimes you have to corner people if you're trying to get to a particular kind of truth." | Sorkin | | 12:58 | "Some of the worst ones also are when I think I know what's gonna make the person interesting. And I've underprepared as a Result." | Adam Grant | | 14:14 | (Musk interview shift) "I could sense he was in this place...so we started really talking about where all of this comes from in him..." | Sorkin | | 15:18 | "...what I'm trying to do in a job interview...is to meet them where they are...hoping they hit the ball back." | Sorkin | | 18:45 | "I am narcissistic enough to know all of the problems. I just don't know how to fix them all." | Sorkin | | 19:49 | "It's a constant sense of trying to make everything better, of trying to fix it..." | Sorkin | | 21:27 | "...most people who've had what I describe as shoot the moon success...still feel like they have something to prove..." | Sorkin |
(29:39 – 37:46)
Book Premise:
Sorkin discusses his new book, 1929, exploring not just the crash but the characters, motivations, and psychology behind it.
"...trying to go back in history and try to understand...what drove them both before the crash to make the mistakes that they made..." (Sorkin, 29:51–31:10)
Revelation:
The American Dream's current incarnation—wealth as celebrity, get-rich-quick—arose from the culture and accessible credit of the 1920s.
“The whole sort of like, get rich quick idea was actually like a very 1920s idea..." (Sorkin, 31:21)
Lessons from 1929:
“We're probably always going to have crashes...the goal probably isn't to eliminate the bubble completely. The goal is to make sure that the bubble doesn't get too far out of hand." (Sorkin, 34:02)
“Speculation is the twin of innovation...Elon Musk could not have had success unless somebody was willing to speculate on him." (Sorkin, 34:02)
"My grandfather, who lived till 92, never bought a share of stock...after that....he really believed that the stock market was this very dangerous place..." (Sorkin, 36:05)
(40:23 – 43:10)
Worst Interview Advice:
"...to show up with these three points that they're supposed to repeat over and over ...the best interviews...are the ones where it feels like the person is actually grappling with the question." (Sorkin, 40:34)
Dream Interviewee:
Michael Jackson—for understanding the psyche behind such a unique and turbulent life.
(41:30)
Hot Take:
"Money is not emotional armor." (Sorkin, 42:05)
A Life Maxim:
"Nothing good happens after 8:30" (rather than the cliché "after midnight"). (Sorkin, 42:16)
On Adam Grant’s Hosting Skills:
Sorkin awards Grant an A- for creating an open and serendipitous space, noting the tradeoff between surprise and prepared (possibly canned) responses.
"But if I were to tell you you did terribly and it's your own podcast, how would that work? Well, I'd give you an A minus. That means there's always room for improvement." (Sorkin, 43:09)
This episode is an essential listen for anyone wanting to level up their interviewing technique, gain insight into the psychology of successful people, or understand the timeless dynamics behind financial booms and busts.