The Power of Regret: Bestselling Author Daniel Pink in Conversation

Warren Esty:

Hi, I'm Warren Esty, Head of Investment Banking at BMO Capital Markets, and this is our quarterly Capital Markets Podcast. We've got a special show to kick off the year. Today I am joined by Daniel Pink, who is the author of five New York Times bestsellers, including his latest, The Power of Regret. His other books include, When, A Whole New Mind, and the number one New York Times bestsellers Drive and To Sell is Human. His deeply researched works have won multiple awards, have been translated into more than 40 languages, and have sold millions of copies around the world. Daniel, welcome and thank you for joining us.

Speaker 2:

Welcome to Markets Plus, where leading experts from across BMO discuss factors shaping the markets, economy, industry sectors, and much more. Visit bimocm.com/marketsplus for more episodes.

Daniel Pink:

Thank you for having me, Warren.

Warren Esty:

I have been looking forward to this conversation. There is a lot to cover and I really want to get into it.

Daniel Pink:

All right.

Warren Esty:

Your latest book is The Power of Regret, and in the book you challenge the no regrets philosophy that I think we probably all ascribe to in some form. So how can organizations apply the insights from the book to foster a culture that encourages learning from mistakes and promotes continuous improvement amongst employees?

Daniel Pink:

Sure. Well, and it's important to understand regret as a human emotion and just how common it is. I mean, truly everybody has regrets. The only people who really don't have any regrets are little kids whose brains haven't developed, people who are sociopaths or people who have certain kinds of neurodegenerative disorders. So everybody has regrets. And I mean it is ubiquitous in the human experience. And so you have to ask yourself, well, why? Why would something so unpleasant be so widespread? And the answer is because it's useful if we treat it right.

And so the problem is that in leadership and in other parts of our lives, we haven't been treating it right. So some of us ignore our regrets. We say, "Oh, nope, always look forward, never look back. Always be positive, never be negative." Bad idea. Others of us wallow in our regrets, ruminate in our regrets, stew on our regrets. Bad idea too. What should be doing is confronting our regrets, looking them in the eye, thinking of them. And this is something I think bankers can do a good job of thinking of as data, thinking them as information, thinking of them as in some ways a market signal.

And when we do that, when we think about our regrets, it's a transformative emotion. People who process their regrets in a productive way become better problem solvers, become better negotiators, become clearer thinkers. And so that's at the big level. At the tactical level for leaders, I think one of the best things that leaders can do is assemble their team and tell the team about a regret that you have. Now, it is not an exercise in self-flagellation.

What you should do is you should say, "Here's a regret that I have. Here's what I learned from it and here's what I'm going to do about it." And what that does is that normalizes this regret and it turns this painful emotion into an engine of progress. And it creates what Amy Edmondson at Harvard and others have called psychological safety. We want to create environments where people can make intelligent mistakes, can take appropriate risks, can try stuff, and not get their head handed to them if it doesn't work.

Warren Esty:

Love it. Okay. I'm going to go out on a limb and see if I can do that with my team. I like it. Thank you. What are some of the most common regrets people have about their careers?

Daniel Pink:

I think the biggest regret that people have in their careers is actually playing it too safe, not taking enough risks. I found this quite fascinating. Now let me take a step back and tell you why I think I know this. As part of the research for this book, I collected regrets from all over the world. We have a database now of we're over 26,000 regrets from more than 130 countries.

Warren Esty:

Wow.

Daniel Pink:

And around the world, people have very similar kinds of regrets and one of them is a regret about boldness. So you're at a juncture in your life, you can play it safe or you can take the chance. And what I found really surprising is that overwhelmingly people regret not taking the chance. Far more people regret not taking the chance way more than people who took a chance and it went south on them.

And this is particularly true in careers. So people regret. I have a lot of people who regret saying, oh man, I'm stuck at this dead end job and I really wanted to go out on my own and be an entrepreneur, but I didn't have the courage to do it. We have a lot of regrets in the workplace about speaking up. "I knew something was wrong, I knew we could do it better. I didn't feel right about speaking up." We have others. There's one that I remember in particular, it's a man from the UK. I found this really poignant.

He said, "I focused on not failing rather than succeeding." And so, one of the things that we see in the research overall on regret is that over time people regret inactions way more than actions. I mean, it's not even close. By the time people are in their 50s, 60s, it's like a three to one ratio between regrets of inaction and action. And a lot of the inaction regrets have to do with, "I wasn't bold enough, I was too timid, I didn't take a chance." And that's especially true in careers.

Warren Esty:

That's really fascinating. And did you see in your research, was there a willingness to be bolder? Was there a correlation with age?

Daniel Pink:

I'm not sure about the willingness to do that. I actually don't know the answer to that question. It is an interesting question. There is some evidence that entrepreneurs who start later in life are actually more successful than those who start earlier. Yeah, so entrepreneurs who start their entrepreneurial part of their careers later, even in their 50s, end up being more successful than those who go out in their 20s. And I think it's partly because they are actually better able to balance the risk and the reward.

Whereas it's interesting on age, what you see is that people in their twenties actually they have about equal numbers of regrets of action and inaction because they're doing stuff. They're doing stuff that they regret. But as people age, it's really these regrets of inaction that take over. And what you don't want in your career, in your personal life, you don't want to get to your 80s or 90s and be sitting there saying, oh, if only I had tried that, if only I had spoken up. You really don't want that. It gnaws at people. And if you know that when you're in your 30s or 40s or 50s or 60s you can do something about it.

Warren Esty:

Totally agree. So given the changes in the workplace, including AI and automation, what skills or behaviors do you think will be the most critical for business success in the next decade?

Daniel Pink:

Yeah, believe me. I mean, that's a question I want to know the answer to myself.

Warren Esty:

It's a big question. Right. Exactly. Exactly.

Daniel Pink:

Yeah. And I took a stab at this nearly 20 years ago in a book that I wrote called A Whole New Mind, where I argued that these so-called left brain skills, logical, linear, sequential, analytic skills were becoming necessary but not sufficient. And it was really right brain skills, artistry, empathy, inventiveness, big-picture thinking that we're becoming more important. I think that's still more right than wrong, but I've been blown away at how good generative AI is at creative tasks.

It's very good at certain kinds of creative tasks. And that's sort of changed my thinking a little bit. So I'm working my way through this. But among the skills that I think are most important, one of them is what I would like to call composition. That is being able to put the pieces together. And I think it's fundamentally an artistic skill. When you have a painter will compose a painting, musical artist will compose a symphony, you're taking all the pieces, you're putting them together. It's like making a deal. That's what a deal is in many ways too.

Warren Esty:

Yeah, absolutely.

Daniel Pink:

You're composing, you're putting the pieces together. You're not only focused on one element, but you're seeing how it works together, how they align and so forth. So it's a compositional skill. I think that's one of them. The second one that I think a lot about now is taste. And I'll give you an example of that. Generative AI by its very nature, by its name, it's in its name, is generative. It can create a lot of stuff. And so if you ask AI, a generative AI tool, a large language model, whether it's Claude or ChatGPT, "Give me a list of 50 ideas," it'll give you a list of 50 ideas.

It's very good at that. Where you come in as an individual is you got to figure out what's a good idea and what's not a good idea. You have to have taste to be able to distinguish between those. And so I use that tool a lot in my writing. So for instance, a good example of it was, I was doing this thing where I was sort of inventing a startup company for fun in something that I was writing that made blue light blocking glasses. So it's like, how about a tech bro company that makes blue light blocking glasses? All right, what would be a good name for that, for the glasses?

So I had ChatGPT give me 25 names, and none of them were very good, then I had Claude give me 25 names, 24 of them weren't very good, but one of them was Blunicorns and I'm like, "I love that name." Because it's funny. See, I laughed the same way that you did. And so you have to have the taste to be able to distinguish those things. So I think it's composition, I think it's taste. And then I also think there's something that you might even call loosely almost like pastoral skills. The skills of a pastor or a clergy person which is kindness and generosity and a sense of meaning. Those have become really important. And that's a very different set of skills. I mean, I know that you have an MBA, you go to an MBA program they're not teaching you taste, composition and pastoral skills.

Warren Esty:

No, that's exactly right. Those three things are absolutely cause for reflection. That's a great answer.

Daniel Pink:

The other thing about them is that I think that they're interesting and I think that they're challenging. We all have taste, we all have preferences. We have foods we and don't like, we have art and music we and don't like. We have a sense of what's good and what's not, what makes a great employee, what makes... And so really honing your taste and exercising your taste. And thinking of yourself, especially as a leader, as a composer, you are composing. And then also, especially for leadership, just these basic skills of just being generous, being kind, helping people see the big picture. AI is not going to be able to do that.

Warren Esty:

That's right. I completely agree. Okay, so in your book, Drive, you emphasize the importance of intrinsic motivation. So how do leaders in traditional hierarchical organizations foster that type of motivation that can be so transformative amongst their employees?

Daniel Pink:

Yeah, I mean, if it's a traditional hierarchical organization, my best recommendation would be to start small and Also just think about what does the science tell us about what really motivates people to do great work over time? And it's less about dangling a reward in front of them and more about giving them a sense of autonomy, some control over what they do and how they do it, a sense of mastery, which is being able to get better at something that matters, make progress, and then also a sense of purpose. I'm not 100% against hierarchies. Basically human civilization has always created hierarchy because they're efficient in doing certain kinds of things, what I'm generally against is over-indexing on control.

That's the most important thing. When we think about autonomy, we can think about the opposite of autonomy, which is control. And what we also know is that even though human beings will naturally form hierarchies in certain circumstances and they can be efficient, what we also know is that human beings have only two reactions to control. They comply or they defy. And if you're a leader, do you want people who are perfectly compliant? Probably not. I mean, you want compliance in the regulatory sense, obviously for BMO or financial institutions and so forth, but you don't want people who say, "okay, I will do exactly what Warren wants me to do exactly the way he tells me to do it." That's not enough.

Warren Esty:

That's right.

Daniel Pink:

You also don't want people who are defying. You want people who are engaged. And the way that people are engaged is by being able to power their own engine. And one way to do that is to give people just a little bit more control over say what they do, what their assignments are, when they come into the office, where they work, how they work. And so notching up the autonomy not from three to 10, but from three to five can play a big role. Helping people see the progress they're making day to day is extremely important, extremely important. And then also the more that you can show people even in a hierarchical system why they're doing what they're doing. Why does it matter that you're doing this well? Does it contribute internally and does it make a difference externally?

Warren Esty:

Great. So staying on the motivation theme, but also now layering in communication, what role does storytelling play in leadership and organizational success, and how can leaders use it effectively?

Daniel Pink:

Yeah, it's a great question and I think it's important and in some ways and in some ways undervalued. We can make a kind of hard-headed case for why it values because we live in a world of ubiquitous facts. There's so much information out there, there's so much knowledge out there that people don't need more facts, what they need in some ways is context, synthesis.

And so what stories are is a way to put facts in context and deliver them with emotional impact that ends up being really important. And I think we sometimes underestimate how much people think in stories, they process the world in stories. When people come home from work and then their spouse says, "Hey, how was today?" They don't say, "Oh, here is my deck, my 14 slide deck with a flow chart explaining it."

Warren Esty:

That's right.

Daniel Pink:

You say, "Oh my gosh, first this happened, and then because of that this happened and then because of that, this happened and in the end this happened." That's how we process the world. So the more that leaders can think and understand that people think in those terms and chart their vision in those terms, chart their marketing campaigns in those terms, and recognize that people are part of a bigger story, that they're actors in a bigger story, I think that can be extraordinarily effective.

Again, it's another one of the things that I think really good leaders pick it up some ways intuitively, but it's something that can benefit from maybe a little bit greater instruction. And also just from things like leaders reading more novels and fewer business books, which something I shouldn't say, my publisher will kill me for saying that, but listen, this year read two fewer business books and two more novels.

Warren Esty:

Right. Right. As I was preparing for this interview and I picked up on the storytelling theme, my thoughts almost immediately went to Winston Churchill. Talk about someone who used almost storytelling to get the British people. And really almost certainly Franklin Delano Roosevelt brought him over the line and kept the English people in the fight when it looked like all was lost, right?

Daniel Pink:

Absolutely.

Warren Esty:

And so your comments about storytelling really resonate with me. And I think as leaders, storytelling with authenticity-

Daniel Pink:

Absolutely

Warren Esty:

... to me is the most important thing.

Daniel Pink:

I'm so glad that you said that because storytelling is not BSing. In fact, that does you more harm than good. It's really about authentic storytelling, telling the truth, and telling the truth in a way that makes what's happening in the moment even clearer. And remember to your point, Winston Churchill, before he became Prime Minister in the middle of this, he's becoming Prime Minister, he was a writer. He was writing popular histories, and so he had a good sense of that, and that skill turned out to be the right match for that moment just as I think it's the right match for this moment.

Warren Esty:

Yep, agreed. Okay. So how do you see the connection between physical health and the ability to cultivate mental focus and discipline in one's personal and/or professional life?

Daniel Pink:

I mean, I truly wish more people would ask that question and ponder that connection because I think the connection is powerful, powerful. I'll give you two dimensions of that. Number one, if you think about something like exercise, I cannot find a single thing in our lives that is unequivocally good for us, except for exercise. I mean that very seriously.

Warren Esty:

No, I agree. I agree. It's a great point.

Daniel Pink:

Every piece of research that comes out says exercise is good for your problem solving skills, exercise is good for your mental health, exercise is good for your ability to sleep. Exercise is good for everything. And I think that organizations can do a better job of encouraging exercise or incorporating it into people's day-to-day activities. I mean, it really is an unalloyed good. And I can't think of another thing in our lives that is so good for us. So that's one thing. The second thing would be, I wrote about this in another book, some really interesting research on breaks and the importance of taking breaks.

It doesn't necessarily have to be exercise, but just taking breaks. We have this idea, and Americans and Canadians and Brits are the worst at this, is that we have this idea that the way to get more and better work done is to power through. That amateurs take breaks, professionals don't take breaks, that it's actually morally virtuous to power through. And it's just not true. We have to think of breaks as part of our performance rather than a deviation from a performance. And so here's why I think leaders can play a role. Leaders can sort of systematically take certain kinds of small breaks and model them for other people. And we know that the ingredients.

You should be taking breaks that are outside where you're in motion, where you're leaving your phone behind, and it's actually somewhat social. And so when breaks that are, as I said, where you're social, not solo, where you're moving, not stationary, where you're detached from your work, just 15 minutes a day can play a big role. And I think it's such an important question you ask because there is this tendency sometimes to think about the people who ourselves, but even the people in our companies as just brains on sticks. All you want. But the thing is, the brain is part of our body. It's all connected here. And so the more physically healthy people are, the better they're going to be at their jobs, the happier they're going to be, better off we're going to be overall.

Warren Esty:

Completely agree. Completely agree. I'd love to hear what your personal routine is to start your day to get you going, to help you maintain discipline throughout the day.

Daniel Pink:

Yeah, if I had to rely on just my own discipline and willpower, I would be toast. So instead, I have become a creature of routine. This is particularly true for writing. What I do, I treat writing as essentially a blue collar job. I think about my writing as a brick layer. So when I'm writing something, I come into my office and I come in at a certain time. I come in at 8:30. I'm not super early, I'm not super late. I come into my office at 8:00. My office is just the garage behind my house. I come into my office at 8:30 and I give myself a word count.

I say, "Today you need to write..." whatever it is, "... 500 words, 600 words, 700 words." Not a massive number, but a meaningful number. I don't bring my phone with me into the office. I don't answer my email. I don't do anything until I hit that number. Some days I hit the number at 10 o'clock. Other days, miserable days, horrible days, days I detest, I don't hit it until 1 o'clock or 2 o'clock or 3 o'clock, but I don't do anything until I hit that number. I don't watch sports highlights, I don't respond to email. It's the only thing that I do. And then once I do that, I can do other stuff. And then I do it the next day and the next day and the next day and the next day and the next day.

And so it's like building. I come in, I lay a few bricks, come back the next day, lay a few more bricks, come back the next day, lay a few more bricks, et cetera, et cetera. If I waited to write until I was inspired, I would not have written anything. Truly. So what happens is, oh my God, at 8:35 I'm like, "Oh my God, I can't believe I have to write 500 words." Then I get over myself at like 8:40, and then I start doing my work. Then I do it the next day and the next day and the next day and the next day. I'm a big believer that structure can be liberating. And so at least for me it is.

Warren Esty:

Well, it's also the consistency of the discipline that you employ, which is really key.

Daniel Pink:

I mean, I am such a big believer in consistency. I mean, I'll give you that. So my first book I wrote in what I like to call heroic bursts. So I would do nothing, and then I would wig out and I would drink like a thermos of coffee and I would write 2,000 words in a frenzy. That's not a good way to do things. In the same way, if you sit on your butt and don't exercise for a week and then say, "Oh, it's Saturday, I got to go run 14 miles." You might do that, but it's going to hurt a lot. You're better off running four miles and then four miles and then four mile. So I am a convert that in almost every realm of life consistency beats intensity. Just consistency, consistency, consistency. And I look for that when I partner with people to do projects on. I look for people who are consistent rather than heroic.

Warren Esty:

So if you could recommend one daily habit to business leaders, any suggestions? Any ideas?

Daniel Pink:

Yeah, I mean, it's going to depend on context. The one thing that I would say, because it's been helpful to me and I know it's been helpful to some other people, is find your MIT, that is your most important task. Really think hard about in a given day, what's the most important thing you have to do today? And do that first. A lot of times we seduce ourselves into thinking that we're being productive when we are answering email, when we're going to meetings, but really setting out that intention, what is my most important task today? And carving out time to do that first.

I found that to be transformative because I was someone who's easily lured into thinking that answering email or doing a call or going to a meeting is productive, when in fact there's certain things that actually make a huge difference today and in the future. And what often happens, I mean, it happens to me, it happens to other people, it's 6:00 it's like, "Oh my God, the most important thing I had to do today I haven't even had time for." So I either have to do it at night or it's like, "Oh God, I just give up and do it again." So if you just take that and do it first, I find that really transformative.

Warren Esty:

Okay, got it. I will try to incorporate that. All right, last question. So you have met and interviewed and collaborated with a wide variety of highly successful people across really a variety of industries. What are some of the most common traits you observe in those successful individuals?

Daniel Pink:

Yeah, it's an interesting question. I haven't really thought that much about it, but I mean, it is a question that it's worth pondering myself. And it's also, I think a great question for people listening. I would love to hear other people's answer to this question. For me, I guess I would say the first one is that they show up. And what I mean by that is they don't say, "I really want to start a company." They show up and write a business plan, and then they show up and they look for investors, and then they show up and they hire their first employee, and then they don't talk about stuff, they show up and do their work.

And that's true in anything, whether they're a physician, whether they're a writer, whether they're an artist, whatever, they show up. And the other dimension of show up is they show up for other people too. So when there are people in their lives who need a hand they show up for that. So it sounds really simple, but a lot of people don't show up. And so showing up is one. The other thing that I would say, and I played around with this, trying to come up with a word to describe it is, the people you're describing, the people who I think are cool or interesting, impactful, doing good things, they seem to have the right mix of confidence and humility.

They're not over-indexed on one. Too much confidence. You're going to make some big blunders, people won't go along. Too much humility, you might not take enough risk. And so they seem to blend. You look at them and they say, "Is that person confident or are they humble?" And the answer is yes, and that's what you want. And so they're not trading those things off, they're recognizing a way that you can be a confident person and be a humble person at the same time. And both of those traits I think are really important in getting stuff done. But also for leadership, people want to follow confident leaders and they want to follow humble leaders. And so if you can somehow figure out how to do both I think that's a freaking secret sauce.

Warren Esty:

Totally agree. Well, look, I could go on for a long time, but I think we need to wrap it up there. Daniel, that was really valuable and I sincerely appreciate you spending the time with us today.

Daniel Pink:

A total pleasure. Thanks for the great questions.

Speaker 2:

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