Leading with Empathy and the Power of Regret with Daniel Pink


In this episode of World Reimagined, we explore the ins and outs of empathy, regret, reflection and change, and how it can make us all better leaders. Listen wherever you get your podcasts.

Our regrets influence the way we engage and interact with the world. Having the ability to reflect and learn from these moments gives us the perspective to better lead while understanding the context, experiences and feelings of others. How can leaders reflect on these defining experiences and moments of regret to make them more empathetic leaders? How can empathy help leaders become more effective?

In this episode, host Gautam Mukunda speaks with Daniel Pink, author of five New York Times bestsellers, including The Power of Regret: How Looking Backward Moves Us Forward, about how leading with trust and empathy can transform workplaces and change how we see the world.

In the architecture of regret, people tend to regret inactions more than actions.
Daniel Pink
You don’t want to be the leader you had. You want to be the leader you should have had.
Daniel Pink

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Literature Referenced on World Reimagined Season 3 Episode 3:

The Power of Regret: How Looking Backward Moves Us Forward, by Daniel H. Pink

Drive: The Surprising Truth About What Motivates Us, by Daniel H. Pink

The Selfish Gene, by Richard Dawkins

Guest Information for Leading with Empathy:

Daniel H. Pink is the author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward. His other books include the New York Times bestsellers When and A Whole New Mind — as well as the #1 New York Times bestsellers Drive and To Sell is Human. Dan’s books have won multiple awards, have been translated into 42 languages, and have sold millions of copies around the world. He lives in Washington, DC, with his family. 

Episode Transcript:

Speaker 1 (00:00):

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Gautam Mukunda (00:16):

What would you do if you could change anything? And how would you do it?

Daniel Pink (00:23):

Instead of having political battles, we have identity battles, which are battles to the death. If there's a norm that I would change it would be to start from the position of trust. And so when we think about "motivating people and organizations", what it really means is creating a context in which people can motivate themselves.

Speaker 4 (00:37):

World Reimagined with Gautam Mukunda, a leadership podcast for a changing world. An original podcast from NASDAQ.

Daniel Pink (00:47):

You don't want to be the leader who you had, you want to be the leader you should have had.

Gautam Mukunda (01:02):

Nope, that's not quite right either. Sure, this has to be ready first thing tomorrow morning, and your team is counting on you, but something about that version just didn't feel quite right. After all, this is the deal of a lifetime, the capstone of your career. It could even be the chance to transform an entire industry. You want this for yourself and for your team, who've worked so hard to get it ready, and who knows when an opportunity like this is going to come along again. Should you grab another coffee? No, no, focus, because you don't want to look back on this moment later and regret it, or do you? Because as strange as it might seem, and as hard as it might be to believe right now, you might not want to live with no regrets.

Daniel Pink (01:58):

I guess one of my big regrets in my life, it comes from when I was younger, are regrets about kindness.

Gautam Mukunda (02:06):

And Daniel Pinkß knows a thing or two about regret, he literally wrote the book on it. He's the New York Times bestselling author of seven books that focus on making work better, not from the top down, but beginning from individual human needs and going from there. His latest, The Power of Regret: How Looking Backward Moves Us Forward, has some surprising insights into what you might glean from things you wish you'd done differently.

Daniel Pink (02:34):

Not kindness in the sense that I bullied people, because I didn't. But I have regrets about kindness through inaction, where I have had been in many situations where people were not being treated right, they were being left out, they were being excluded, they weren't being treated fairly. And it wasn't like I didn't see, I saw. It wasn't like I didn't know it was wrong, I did know it was wrong, but I didn't do anything, and that has bothered me for years and years and years and years and years. And finally, I just, sort of in some ways the usefulness of regret, it's like, "God, why is this bugging me so much?" And the reason is that it's very clear, it's, I value kindness. So regret is clarifying what I value, in this case, kindness, and it's also instructing me on how to do better. And so I tried to be more kind in those kinds of situations, particularly in situations that involve bringing people along or including people in things.

Gautam Mukunda (03:25):

So I find it striking, I bet if we asked a hundred people, that almost all of them would start out with something from their childhood, and it sounds like that's what you grabbed onto. So for me personally, when you said... I dealt with bullying when I was in school and my regret weirdly is every teacher and every security guard in my high school would've been happy to help out, and my regret is I didn't go to them for help.

Daniel Pink (03:45):

Oh, interesting.

Gautam Mukunda (03:46):

And then, so now, one of the things when I teach, and I teach leadership which has a big ethics component, things like that, one of the things I wish to teach students is, do not be afraid to ask for help.

Daniel Pink (03:54):

Yeah, that's good.

Gautam Mukunda (03:56):

Right? And I don't know how much of that is driven by that regret of, why did 14 year old me not realize there were people out there desperate to help him and not go to them?

Daniel Pink (04:03):

It could be. I mean, I think part of that also is, I think there's a measure of maturity in all of this too. But what I find is that the incidents that people regret are not only from childhood at all. I mean, my kindness regrets are not only from childhood. I mean, maybe it's sadder, they actually extend to when I was a young adult.

Gautam Mukunda (04:19):

And so that's a great [inaudible 00:04:22], we wish you had thought of kindness as a more of an active than a reactive stance. Are there other things that you would put in that category?

Daniel Pink (04:27):

Active, not reactive, that's an interesting way to put it. Yeah, I think that's probably right. I mean, I think that part of it also is that one of the things that you see I see in my own research and it's very clear in the overall research on regret is that in the architecture of regret, people tend to regret inactions more than actions. And so both of us, not only are they childhood regrets, but they're regrets of inaction, something we regret what we didn't do. So I think that in some ways is as instructive.

Gautam Mukunda (04:57):

Instructive, isn't a word normally associated with regret, case in point, the verbs Dan uses to describe most reactions to this emotion are far more negative. But there is something about looking back wistfully at the path not taken that can drive you to become a better leader.

Daniel Pink (05:13):

The thing about it is that regret isn't only about outcomes, regret is also about the decision you made at that particular moment. So I've collected regrets from all over the world. I have a database of 20,000 regrets from people in 109 countries, and I have a lot of people who regret not asking people out on dates. And when you interview those people, they don't say, "Oh my God, if I had asked him out, I would be leading a life of bliss." They don't necessarily conjure a counterfactual world where everything is perfect. I think what really bugs them, what really gnaws at them is at that moment they didn't step up and do something.

Gautam Mukunda (05:48):

So to me that strikes at the heart of the discussion about regret, that it's almost less about the outcomes than what it says about the person you were at that moment in time.

Daniel Pink (05:55):

Oh, that's interesting. Yeah, I think that's part of it. Yes and no. I mean, it's the person you are, but also it's really as much of the decision you made. And one of the things that we know in kind of just overall wellness and overall psychological wellbeing is that, especially when we look at our mistakes and our screw ups and our setbacks, it's important to evaluate the decision and the behavior and not make a universal claim about the person.

Daniel Pink (06:21):

One of the reasons... And in fact, one of the antidotes for regret bringing us down, because again, how we deal with our regrets is actually really important, regret is one of our most common emotions and it can be one of our most transformative, but it also depends on how we deal with it. So we can ignore it, that's a bad idea, or we can wallow in it, that's a bad idea, an even worse idea in many cases. And one reason that people wallow in it is that they don't recognize that their mistake, their regret, whatever it is, is a moment in their life, not the full measure of their life. They use that mistake to make a universal declaration about who they are as a human being, rather than an assessment of how they behaved in that particular moment.

Gautam Mukunda (07:02):

So do you know Rose McDermott? She's a brilliant political psychologist, she studies international relations but she has a deep training in psychology. And so Rose one said to me, "There is no such thing as personality, it is all about context." Right? And I was like, "Well, I think that goes a bit far." But she's like, "No, no, if that's what you believe, you are way closer to the truth than people who are the other way around."

Daniel Pink (07:22):

I mean, what you're identifying there is that actually a reasoning mistake that Westerners especially make, which is that when we try to explain people's behavior, when we try to predict people's behavior, we almost always go to, "He did that because he's an introvert. She did that because she's neurotic. They did that because they're unkind." And we want to explain things in terms of the person's personality, disposition, fundamental state, rather than explain it in terms of the situation, the context, the environment that they're in.

Gautam Mukunda (07:55):

The fundamental attribution error is one of the most important findings from all of psychology. It's so important, in fact, that it's named the fundamental attribution error. In essence, it finds that, at least in Western cultures, when explaining someone else's actions, people over attribute the importance of individual personality and disposition and under attribute the importance of situation and context.

Gautam Mukunda (08:20):

Think about a time you failed, when we mess up, we tend to believe that it was due to context, that we were in a situation that made this failure more likely. When someone else fails, however, we tend to attribute it to their individual characteristics like personality, capability or intentions. When I do a bad thing, it's because I'm in a bad situation, but when someone else does a bad thing, it's because they're a bad person. Psychological research tells us that the former judgment is the right one. In general, situation is far more powerful than personality. So if you want your shortcomings to be judged on context rather than what they say about you, why should it be different for anyone else? Maybe it's time to rethink the way we as leaders view the people on our teams and ourselves as well, because these old strategies, they aren't working. So rather than attribute qualities to others based solely on your measure of them, maybe a better place to start is by putting yourself in their shoes.

Daniel Pink (09:23):

We are hardwired for empathy, but we are, I'm going to hit that word hardwired, but we do have a propensity for empathy, but we tend to empathize mostly with people who are like us. And that might have an evolutionary basis because the more we recognized people who were like us, the more likely our genes were to propagate into the next generation. And so we empathize with our in group and actually not with our out group because evolution has programed us to do that.

Daniel Pink (09:51):

Now we can obviously overcome evolution and we can widen the circle of people when we should widen, so as a prescriptive thing, we should absolutely widen the circle of people we have empathy for or have compassion for. We should absolutely empathize with people who aren't like us. Again, I think some of it comes down to being over indexed on our own specialness. So we think that, "Oh, well, I can't empathize with that person because that person is a woman rather than a man like me." Or, "That person is a Patriots fan, not a Steelers fan." Or, "That person is a Democrat, not a Republican." We empathize with our in group, as a prescriptive matter we should empathize with everybody, except for maybe if you don't like the Steelers.

Gautam Mukunda (10:32):

I would struggle to empathize with someone who is a Cowboy's fan, that would be hard.

Daniel Pink (10:35):

Okay, all right, that's fair.

Gautam Mukunda (10:37):

But so what's your advice to people on how to overcome that? Let me start with that.

Daniel Pink (10:41):

Well, I mean, I think that we have advice from... I don't think my advice is original because I think it comes from essentially every religious tradition, which is, treat people like you would have them treat you.

Gautam Mukunda (10:51):

So this is [inaudible 00:10:52], because when I think about the way you put them right, the in group and the out group, one could say that the story of, certainly the last two centuries of American history and hopefully for much of world history, is the steady expansion of who we include in the in group.

Daniel Pink (11:05):

Okay, interesting point. Yeah.

Gautam Mukunda (11:06):

Right, that you went from... When we said all men are created equal, that's not really what we meant. And at some point we got to that, and then hopefully it became all women are created... There was this sense of the in group kept getting larger and larger. So we think of that as an unalloyed good. And obviously I would much rather have... It is overwhelmingly good, nobody would want to go back to the thing when we didn't mean it when we said all people are created equal. But let me ask you then, if, when you're a leader, is there a downside to this that as the group becomes more and more diverse, the bonds of the group start to weaken? And what would you tell leaders about how to counteract that, if that is a problem?

Daniel Pink (11:45):

Well, on that one, I would appeal to a superordinate identity. That is, while superficially we might have a different identity, you might have one color skin, I might have another color skin, you might pray to this God, I might pray to that God, that at a superordinate identity, we are all part of this team with this mission. I think that's a way to surmount it.

Gautam Mukunda (12:07):

Ronald Reagan once said that he thought that world peace would only come if we were attacked by aliens, [inaudible 00:12:12].

Daniel Pink (12:11):

That's interesting. So I think part of the problem in our politics right now is that it's completely identity based. I mean, you're political scientist, this is Lilliana Mason's work, that essentially that all of our politics has been captured by identity, that politics and identity line up perfectly. So we no longer have say relatively few white Christians who believe in the democratic party or the Left and relatively few people of color who are nonbelievers, who believe in the Republican party or the party of the Right, that it's lined up perfectly and that as a consequence instead of having political battles, we have identity battles, which are battles to the death.

Speaker 4 (12:49):

You're listening to World Reimagined with Gautam Mukunda.

Speaker 5 (13:00):

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Gautam Mukunda (13:33):

Changing norms around empathy is hard, but not impossible. In his groundbreaking work, The Selfish Gene, biologist Richard Dawkins posits, "That although human beings are like every other living creature, subject to the demands of our genetic code, we're unique in that our brains grant us the ability to counterman that code." So while our biology pushes us to empathize only with those we look like or agree with, Patriots fans, for example, the complexity of our brains lets us look past that and empathize even with those with whom we have little in common.

Gautam Mukunda (14:07):

If you took a poll anywhere in the United States, I bet that pretty close to 100% of respondents would say that's the right thing to do, but proving it's easier said than done is as simple as turning on the TV, opening a newspaper or logging into Twitter. It's hard to empathize with people who are different from us, especially in a world with so many identity lines drawn in the sand. So I asked Dan if he were leading an organization and wanted to get around that, what's the first thing he would change. What norms would he break down? At first though, he took my question in a slightly different direction.

Daniel Pink (14:43):

If I were leading an organization, the social norm would be to talk to the board of directors to find a new leader. I should not be leading an organization.

Gautam Mukunda (14:52):

I remember when William F. Buckley ran for mayor of New York City, sort of, as a joke, somebody asked him, "What is the first thing you will do if you win?" And his response was, "Demand a recount." Okay, so if you were advising a leader, what's the social norm... [inaudible 00:15:08] because you've written books on so many different topics, what's the social norm you'd tell them they should work hardest to change?

Daniel Pink (15:13):

That's an interesting question. Maybe the social norm that I would try to institute would be to start from a position of trust with everybody rather than a position of skepticism or lack of trust. And I think a lot of times inside of organizations, leaders, when they're dealing with people, they don't start from that position of pure unequivocal trust, instead they start from saying, "You know what? I don't know if I can trust you. I don't know if you can be autonomous. I don't know whether you're going to do the right thing, so I'm going to wait till you prove yourself before I trust you." And I actually think that's the wrong starting premise in most cases. And so if there's a norm that I would change it would be to start from the position of trust. Now, some people are going to prove untrustworthy, but most are going to prove trustworthy, and so I think there are efficiency gains with that too.

Gautam Mukunda (16:01):

So what, you could even root this in game theory, right? With the prisoner's dilemma, right? We always say with tit for tat, but tit for tat only works properly if you start with a position of trust. Because if you start by defecting, you and your other opponent will get trapped in a cycle of perpetual-

Daniel Pink (16:14):

Yeah, that's an interesting way to put it. Yeah, I think that's right. And so if the norm becomes, around here we trust each other, around here we assume that everybody has positive intent, around here we give people the safety to make mistakes, I think that's powerful.

Gautam Mukunda (16:30):

So all of those, to loop back to our empathy, those are all things that I think you are much more likely to do if you have empathy for the person you're interacting with.

Daniel Pink (16:39):

Probably, yeah.

Gautam Mukunda (16:40):

So let's give our listeners free consulting. I think that's a wonderful social norm change, right? We should be an organization that defaults to trust. We start with a default trust. How would you help people get there?

Daniel Pink (16:51):

I would do things like get rid of as many controlling mechanisms as you possibly can. So for instance, things like the kind of monitoring that takes place in a lot of workplaces, recording keyboards, recording the clicks that people make on their keyboard, I would get rid of that. So anything that's controlling like that. I think a lot of these if then rewards, these very high stakes contingent rewards, are a form of control too. So I would get rid of those and replace them with something less controlling. I would also give people a much greater discretion about, we see this in the aftermath of the Great Resignation, is give people much greater discretion, not complete, but much greater discretion over what they do, how they do it, when they do it and where they do it, particularly when they do stuff and where they do it.

Gautam Mukunda (17:40):

In The Human Side of Enterprise, Douglas McGregor proposed that managers generally have one of two views about people's motivations. The first and more common one, which he dubbed, theory acts, is that people are fundamentally lazy and a manager's job is to force them to work. The second theory why is that people want to contribute, that people want to be useful and a leader's job is to put them in a place where they can thrive. There are examples of successful companies with both philosophies, but the more power employees have in the labor market, the greater theory wise advantage becomes. That's exactly what we are seeing today with the Great Resignation, which has pointed us towards a lot of norms that might be bound for the cutting room floor. But I wanted to ask Dan, where does this nagging instinct to constantly look over our team's shoulders come from? And since we all agree, it needs to be done away with, what do we put in its place?

Daniel Pink (18:34):

I think part of it has to do with human nature. That is, we don't like uncertainty and with lack of control there's more uncertainty. With control at least there's uncertainty, there's not necessarily productivity or improvement or accomplishment, but there's a greater degree of certainty. It might make the people who are exerting control feel like they're effective, like they have some self-efficacy, I think that could be part of it.

Daniel Pink (18:57):

The other thing is that controlling mechanisms were not necessarily that bad with certain kinds of ways of production. That is, there's certain kinds of economic activity where rigid standardization is actually the way to do things better. If you're working on an assembly line or if you're just cranking out mass produced goods, and you're trying to do that at a volume at a low price, then maybe control has some virtues. But when you're dealing with work that requires judgment or creativity or discernment, control doesn't work. Because again, human beings have only two reactions to control, they comply or they defy. And in those kinds of jobs, jobs again, that require conceptual thinking, or even a modicum of innovation or judgment or interaction with other human beings, you don't want people who are purely compliant and you don't want people who are purely defined, you want people who are engaged. And the way that people engage is by getting there under their own steam.

Gautam Mukunda (19:55):

Was there a particular experience or research finding that sort of shaped your views and brought you to this?

Daniel Pink (20:01):

On that particular point of view, no, it was actually... No, there's no signal, and it's really the accumulation of things. It's really the accumulation of a lot of this research showing that control leads to compliance, generally, or to defiance, but it very rarely leads to any form of deep engagement. Now that's also, I think, consistent with my own experience as a human being on this planet. It's also, I think, consistent with what we know about human beings more broadly. So if we think about something like, when I talk about, like I did in Drive, is the notion of autonomy. And when I talk about this notion that people want get better at something that matters, master it, that they want to know why they're doing something, a purpose. I think at some level that is human nature.

Daniel Pink (20:42):

If you look at a kid, you show me a two year old or a three year old, every two or three year old is going to be autonomous and self-directed, every two or three year old is going to want to learn and grow and master stuff for the sake of it. Every two or three year old, three to four year old wants to know why stuff is happening. And so I think that that's in some ways who we are and that certain experiences, again, we're back to this notion of the interplay between the essence of who we are and the context that we're in. I actually think that that is human nature to be autonomous and curious and purpose driven. I think that when we're put in situations and environments, certain kinds of schools, certain kinds of work settings, we change that default setting. But I think the default setting is what I described, I think that's who we are as human beings.

Gautam Mukunda (21:26):

What makes it so hard for some people to get to this space?

Daniel Pink (21:30):

I think they don't know how to do it, and I think that they've somehow been brought up in a world where leadership means control, but I think people are teachable.

Gautam Mukunda (21:38):

Nothing that's come before is set in stone, not really. If there are things to be changed, we can change them. And if that requires teaching your team a new and better way to do them, then as Dan says, "People are teachable." But how can you, as a leader, teach by example?

Daniel Pink (21:57):

I think a lot of times we want to have everything figured out. And so we say, "Okay, leader, I figured this all out. Here is your three step plan, do exactly this." And I'm not sure it always works that way, especially in times like these. I think what we're better off doing is trying one small thing. So for a leader saying, "Okay, let me tell you one regret I have about my last job, okay? Here's what the regret was, here's what I learned from it and here's what I'm going to do going forward. Try that and see if it works. If it works and if it's useful, keep doing it. If it's not, make amendments and do something else."

Gautam Mukunda (22:30):

So is there an analogy to the writing process for you? I always tell students, "You don't understand something until you've written it down."

Daniel Pink (22:37):

I agree with you completely about that. Yeah, no, I think that there is a... I mean, I just think conceptually, we tend to think that we have to have it figured out before we can take action, when in fact action is a form of figuring it out. You mentioned this earlier, the research on writing the same thing down over and over again. I mean, if you can get people to put a bumper sticker on their car, they're going to be more likely to believe in the cause for which they put the bumper sticker on there. We think that the only way to get people to put a bumper sticker on their car is to believe in a particular cause, but a lot of times just getting them to put a bumper sticker on their car, solidifies their belief in that cause.

Gautam Mukunda (23:13):

So, I mean the summary bullet point of that is essentially that we think that beliefs drive actions, but actually it's actions that drive beliefs.

Daniel Pink (23:20):

The arrow goes both ways.

Gautam Mukunda (23:21):

It goes both ways, yeah.

Daniel Pink (23:22):

And our mistake is that we think it singularly goes in that first way, that belief always drives action. When, in fact, action drives belief a lot more than we realize.

Gautam Mukunda (23:30):

So then there's, well, we're thinking about this sort of keystone idea of empathy and trust, there's this sense that by talking about your regrets, showing empathy as a leader, showing trust as a leader, those aren't just expressions, that they're actions. The actions can shape both your own preferences as a leader, but also those are the people around you who are role modeling off of you.

Daniel Pink (23:49):

A hundred percent agree.

Gautam Mukunda (23:51):

So I, by investing in your empathy, am sharpening my own and reinforcing my belief in its importance and also helping you to do the same.

Daniel Pink (23:59):

Well said. I've turned into your Hallelujah chorus here.

Gautam Mukunda (24:03):

Thanks, Dan. I'll take writing tips from you anytime, so I appreciate that. What's the thing that you would want people to take from that philosophy? If you were going to give them the piece of advice on how to do this right, what's the thing you would tell them?

Daniel Pink (24:19):

On how to do what right?

Gautam Mukunda (24:19):

How to create the environment that, I think you and I both feel, is the one that people want to be in, the one that will actually get people who like it, and that will also be productive, right? And this is a real case where almost all good things go together.

Daniel Pink (24:32):

Yeah, no, I mean, I think you already articulated it. At some level you want to create the environment that you would want to be in. You don't want to be the leader who you had, you want to be the leader you should have had.

Gautam Mukunda (24:44):

Isn't that what we all want at the end of the day, to be the leader we should have had? How else are we supposed to make progress as organizations, countries, or even as species if we can't recognize the failings that came before us and sometimes from us and do better? So I wanted to know who in Dan's life had impressed him and inspired him to be better.

Daniel Pink (25:08):

This is going to sound strange, but one of the people who I found more impressive in person than from afar was Oprah Winfrey.

Gautam Mukunda (25:17):


Daniel Pink (25:18):

I did an interview with her and she was so incredibly well prepared, so incredibly engaged in the conversation, so incredibly not fake kind, but decent and direct with the people who were working with her, that I was really blown away by what a huge talent she is.

Gautam Mukunda (25:39):

Wow, because she's really impressive from a distance. So that really says something.

Daniel Pink (25:42):

She's very impressive from a distance, I found her more impressive in person.

Gautam Mukunda (25:49):

So you've got a few hours to go, your team needs you to do your absolute best so that they can give theirs. So stop and think for a moment about what they need, a leader who shares what they wished they'd done differently and doesn't shy away from their regrets, who can empathize with them even when they don't see eye to eye, who doesn't just motivate them to work, but encourages them to thrive. And if that isn't the way you were brought up in this organization, well, there's still time. There's time left to change, to look at the norms and the examples that you had and say, "I am going to do better." Mm-hmm. And if you do that, if you make that change, your team may look back a week, a month, maybe even a year from now and say, "That was exactly the leader we needed to have."

Speaker 4 (26:52):

World Reimagined with Gautam Mukunda, a leadership podcast for a changing world. An original podcast from NASDAQ. Visit the World Reimagined website at nasdaq.com/worldreimaginedpodcast.

Speaker 6 (27:06):

Gautam Mukunda does not speak on behalf of Rose Park Advisors, LLC, or any of its affiliates, and is not soliciting investments or providing investment advice.

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