Career & Success

No Regrets: How to Take Risks in Your Communication, Relationships, and Career

In this podcast episode, Dan Pink shares why we often over-index on risk.

May 30, 2023

“What people regret over time are things they didn’t do. They didn’t take that trip, they didn’t ask that person out on a date. They didn’t start that business,” says former political speechwriter and author Dan Pink. “I think it’s because we are slightly over-indexed on risk. We overstate the risk in many circumstances.”

In this episode of Think Fast, Talk Smart: the podcast, strategic communications lecturer Matt Abrahams sits down with Pink to hear how we can take more risks and how leaders can inspire others by focusing on the why instead of the how.

“There’s almost incontrovertible evidence that a sense of purpose is the most cost-effective performance enhancer that organizations have,” Pink says.

They also discuss the power of taking breaks, which Pink considers part of performance, not a deviation from it. “What we know from many domains is that professionals take breaks. It’s not that amateurs take breaks and the professionals don’t, it’s the exact opposite.”

Pink’s latest book is The Power of Regret, How Looking Backward Moves Us Forward.

Think Fast, Talk Smart is a podcast produced by Stanford Graduate School of Business. Each episode provides concrete, easy-to-implement tools and techniques to help you hone and enhance your communication skills.

Full Transcript

Matt Abrahams: Communication is about risk taking. Many of us are held back by our fears and concerns about what might happen. Today, we’ll explore having a bias for action and being direct in immediate with our audiences. I’m Matt Abrahams and I teach Strategic Communication at Stanford Graduate School of Business. Welcome to Think Fast Talk Smart, the podcast.

Today I am super excited to chat with Dan Pink. Dan is the author of five New York Times bestsellers, including his latest, The Power of Regret, How Looking Backward Moves Us Forward. Early in his career, Dan served as a political speech writer, including being chief speech writer to Vice President Al Gore. Welcome, Dan. I am so looking forward to our conversation.

Dan Pink: Matt, it is great to be here. A longtime listener, first time guest.

Matt Abrahams: Thank you. There’s so many things that I want to talk about. I just want to jump right in. Many of our listeners find themselves preparing presentations and structuring speeches. Earlier in your career, you served as a speech writer, and I’m curious, what two or three lessons can you share for how to prepare and deliver a great talk?

Dan Pink: Well, I mean, political speech writing and political speech giving, I think it can be different from giving a sales presentation or giving a lecture at a university. However, I do think that there are some principles of that realm that we can extract for other realms. So one of them would be audience first. All right? You gotta think about the audience. What do they know? What don’t they know? What do they care about? What don’t they care about? And one of the things that we did, if it allow me a small tangent here, is back when I was working for, as a chief speech writer for Vice President Al Gore, is that when he went out into America, you know, outside of Washington to do things, we would always work massively to find what we called How the hells? Okay how the hell’s, and how the hell would be something like this?

Dan Pink: It’s like he would get up there and say, ‘Oh man, you know,’ (I’m making this up. You’re in Sheboygan, Wisconsin.) It’s like, ‘Sorry, I’m a little bit late, but I wanted to have a second cinnamon roll at McGillicuddy’s.’ And the reactions to the crowd would be, ‘how the hell does he know about McGillicuddy’s?’ Everybody in Sheboygan knows about McGillicuddy’s. So, but the idea of thinking of the audience first, I think is a really important principle. Another one would be, which I’m violating right now, is say less. There has never been a speech, certainly political speech, where people at the end of it said, gosh, I wish he or she would’ve talked longer. Say less

I remember one time seeing these in the White House. These speeches circulate. There was a speech, not ours that was circulating, and it was a draft of a speech. It was Clinton’s speech where the draft of the speech literally said, ‘and my plan has 14 pillars.’ And I’m like, this is not going to stand up with 14 pillars. That’s about 11 pillars too many.

And then the final one is especially for political, but I think it’s true for other realms, is that ultimately you have to think about the purpose. The purpose of the speech is to galvanize action. It’s not to show how smart you are, it’s not to sort of give your own wizardry about your mastery of a topic, especially in political speeches. You want them to do something, you want them to go and vote. You want them to go cater for a higher minimum wage. You want them to try to stop the other side from doing X, Y, or Z. And so when you think about these things, audience first say less, and ultimately you want the audience to act. I think those are helpful lessons for any communicator.

Matt Abrahams: Absolutely, they are, and they have been echoed in many different ways across this podcast. But having a clear goal, knowing what it is you want, being very concise and connecting your content in a way that’s relevant and meaningful. And I love the ‘how the hell’ point. And I think that’s, that’s a great thing for people to think about. It’s, it a little specific details that demonstrate you’ve spent time thinking about and appreciating who you’re speaking to can go a long way. I, I really appreciate that.

Dan Pink: I mean this mostly in, in the realm of corporate communication, which includes speech giving, but includes sort of the way, in many ways, the ways that companies interact with their employees and interact with their customers. To me, the embodiment of how to do it wrong is the phrase we apologize for any inconvenience this might have caused you. Now that phrase, which all of us have seen has been said by faceless corporations, but has never been said by a human being. Human beings don’t talk that way. You and I happen to be conversing right now via the magic of the internet. We are not in the same physical space, but suppose that we were in the same physical space, we were in the same studio, and I am a clumsy guy. I guarantee I will knock over the microphone at some point during this conversation.

So let’s say you and I were together and I had a cup of coffee, and because I talk with my hands because I’m clumsy, maybe I spill the co I spill coffee on you, right? You’re wearing a nice gray sweater. I spill my dark black coffee on your beautiful gray sweater. What would I say under those circumstances? I would not say, ‘oh, Matt, I’m sorry for any inconvenience this might have caused you.’ What, what would you, I would say, ‘oh my God, Matt, I’m so sorry. I can’t believe I did that. I’m so sorry. What can I do to make it right?’ And so I think that the more we just forget the performative side of saying, oh, this is how official language is, this is how companies talk, this is how a smart person’s supposed to talk. And we just talk like we talk. I actually think that it’s more compelling what you’re doing, especially with, let’s go back to speeches. I think a lot of written communication as well. What you’re trying to do is you’re not trying to sound like somebody else. You’re trying simply to sound like a better version of yourself. That’s the key. When I was in college, I was a linguistics major. So if you and one of the few things that you learn in linguistics is the ability to go very meta very quickly. And I can go very meta very quickly on you. When we think about this just in terms of the human species: human beings have been conversing as you and I are, human beings have been conversing for 200,000 years, right?

It is not anything we learned. We didn’t learn how to converse. It is who we are. It’s part of our evolution as a species. And we’ve been doing it for 200,000 years. We have been writing, you know, written communication for only 5,000 years. Like a fraction of that time written communication is an invention. It is not something we do naturally. And then if you think about the distribution of written information, the printing press, that’s only 500 years-ish old. And so we’re learning how to do this kind of written communication, this formal communication. And for whatever weird reason, we have diverged from what we already do as an evolutionary ability. And so the more you can, I guess, let’s be practical here. The goal has to be to sound like a better version of yourself, not to sound official, not to sound like somebody else, but to sound like a slightly more organized, more coherent version of yourself.

Matt Abrahams: Clearly when we communicate, we want to avoid distancing ourselves from the people we’re talking about. You know, in my field, we talk a lot of what you said resonates in and is captured by this idea of immediacy. You want to connect and you want to be immediate, and you use language that is inviting to people. I recently coached a very senior leader at a tech company, and he was giving a presentation for 3000, 5,000 people. And he started by saying, knowledge workers must, and I stopped him. I said, who’s in the audience? He said, knowledge workers. And I said, so why don’t you just say you all right? I mean, we need to communicate and use language that invites people in and doesn’t distance ourselves. I do think many of us think that to sound smarter, we have to use big words and formal Exactly. Ways of speaking. And what I’m hearing you say is, being a better version of yourself is not using big words, it’s just connecting and really thinking about your point and how it can resonate. Is that right?

Dan Pink: Yes. Being a clearer version of yourself, not having this kind of fantastical notion of what official speak is or what smart speak is. And the thing is, it’s like we have in our brains, literally the programming that allows us to do that. That is, like, to me, it takes more cognitive effort for a company to come up with this ridiculous, we’re sorry for any inconvenience this might have caused you. Rather than saying, ‘oh my God, we’re so sorry, we messed up.’

Matt Abrahams: Absolutely. I love the mantra. Speak like a human. And I think all of us can take the time to practice and run our communications by other people and, and have as, as the first threshold. Did it make sense? And does it sound conversational.

In your writing and speaking, you’ve studied a lot about persuasion and selling. You talk about focusing on problem finding, not problem solving. Can you define these two concepts and explain how to leverage problem finding in being persuasive in selling?

Dan Pink: So problem solving is addressing a clearly stated issue that already exists and likely has a solution. Problem finding is actually surfacing when people don’t know that it exists right now. Why is one now more important than the other? This is a big deal because problem solving is becoming a commodity. And this is particularly true, this is true throughout white collar work, but it’s particularly true in sales. If I am in the market for, I’m looking around my office here. If I’m in the o, if I’m in the market for a vacuum cleaner and uh, oh my God, my floor is dirty, I need a vacuum cleaner, and you’re a vacuum cleaner salesperson, I don’t really need you very much. I know what I need. I need a vacuum cleaner. I can go online, I can find the best price I can, I can find the best model for that, for that vacuum cleaner.

You’re not very useful to me. I don’t need you. Right? Your ability to solve that problem and get Dan a vacuum cleaner is meaningless. However, where are you more useful? You’re more useful if that’s not actually my problem, if I’m wrong about my problem. And so maybe the problem is that I have crappy screens on my windows here and all this kind of gunk is getting in here and it doesn’t matter whether I have a vacuum cleaner. So if you can sort of surface a problem that I don’t realize that I have that is more difficult to commodify and therefore there’s a greater premium on problem finding rather than on problem solving.

Matt Abrahams: I love this notion of really flipping the script. It’s not about giving the solution, it’s about finding what’s the right problem. And it gets back to something you said earlier about really knowing your audience and understanding their needs can help you find the problems that can be beneficial to them.

Dan Pink: Well, that’s a huge question, and I don’t have to offer at the start with mea culpa, because in that book, I don’t think I really got purpose quite right. I think about it differently now than when I wrote that book. No refunds for anybody, but I still think about it differently. There’s still value. There’s still value. Yeah. And so what we think of as purpose, particularly when it comes to on the job, is that I’m going to be more motivated to do something if my job is connected to something larger than myself. So not only am I filing this report or doing this audit, but I’m doing it in the service of stopping the climate crisis. And we have a lot of good evidence in organizational behavior that that is absolutely a performance enhancer. If you go to say, university fundraisers and show them letters from people who were on the receiving end of the money that they raised, or have them meet people who benefited from the money that they raised, they raised money.

So purpose is an inherent performance enhancer, but there’s also a quieter kind of purpose where you’re not only making a difference, you’re just making a contribution. We can think of one as capital P purpose. My work is solving the climate crisis. I’m feeding the hungry. But there’s another one where you’re just making a contribution. There’s a great study out of Harvard Business School showing that in a cafeteria when they rigged up an iPad that allowed the cooks to see the customers, the quality of the food improved. And what that meant was that the cooks were not getting paid more, the cooks were not feeding the unhoused, the cooks simply saw the purpose of what they were doing. They were making a contribution. And when we think of it, capital P purpose, am I making a difference in the world. Small p purpose, am I just making a contribution?

I’m cooking a cheese omelet and someone’s going to eat it. I’m going to up my cheese omelet game a bit. My colleague is having difficulty getting a report out the door. I’m going to help her do that. It’s not going to change the world, but it’s a contribution to another human being. I’m at a call center and somebody calls in and they have this problem with their headphones aren’t working properly, and I’m going to solve their problem. I’m not changing the world in any way, but I’m making a contribution. And what we see, it’s really exciting, is that a lot of times, especially in leadership, we’re over-indexed on how leaders always tell people how to do stuff. They don’t explain enough about why what people are doing is important, why it matters, why it connects to making a contribution or making a difference. And as gooey as that sounds, I think there’s almost incontrovertible evidence that why that sense of purpose is the most cost effective performance enhancer that organizations have.

Matt Abrahams: It’s really a catalyst, right? By helping people understand why they’re doing what they’re doing. And, and it’s predicated of course on leadership, understanding what their mission and vision is, and then helping people understand how they play in that. But that’s a great way to enhance the performance you’re looking for.

Dan Pink: And it goes to what we’re talking about before, which is the importance of the basis of a lot of what you’ve been working on for all these years, which is the importance of conversation. And that management leadership is not about dictation. It’s not about one way direction. It’s about a conversation and a conversation to elicit the very best from people includes instruction and guidance on how to do things, but it also surfaces why people are doing things, why what they do matters, why it connects to something else.

Matt Abrahams: And by empowering people with the why, you can motivate the behavior that you’re seeking. Many of those listening get very anxious and nervous about their communication, be it presenting, making small talks, speaking up in a meeting, asking somebody out on a date. In your newest book, the Power of Regret, you discuss the role of risk as it relates to regret. Can you talk about how our perceived risk often does not match the actual risk and the implications that it might have for our motivations and our anxieties and, and maybe even specifically to communication?

Dan Pink: This is, I think, a big takeaway from that, from that book. In that book, I looked at, this misunderstood emotion of regret. And among the things that I did is I collected regrets. Now we have about 25,000 regrets from around the world, and I also did a big survey of the US population about their attitudes on regret. And one of the things that you see, let’s go start with the US public opinion survey. We did this very large sample to try to find demographic differences in what people regret, how they regret it, so forth. So we oversampled in every demographic category, we spent a lot of money to try to find these demographic differences. And there weren’t that many, but there was one big one that goes directly to your point, which is this: in the architecture of regret, you can have regrets about action and inaction, regrets about what you did and regrets about what you didn’t do.

People in their twenties had about equal numbers of action and inaction regrets. But as people age, really just almost like into the thirties, but certainly forties, fifties, sixties, seventies, eighties, the inaction regrets took over. There’s about a three to one, two to one, three to one ratio of regrets of inaction over action. What people regret over time are things they didn’t do. They didn’t take that trip, they didn’t ask that person out on a date. They didn’t start that business. And I think it’s because we are just a slightly over-indexed on risk. We overstate the risk in many circumstances. Now, this is not a lesson to take risks all the time. You want to take smart risks, but I feel like we need to adjust the dial one or two clicks. And this is particularly true when it comes to communication. In what I call the world regret survey, where collected regrets from all over the world.

One of the big categories of regrets were what I call connection regrets, where you have a friend or someone you care about deeply, but maybe you haven’t talked to them for 10 years. You want to reach out, but it feels really awkward and you think they’re not going to care. So you don’t, that is a colossal mistake because it’s a colossal forecasting error. Because what happens is that when you do reach out, it’s way less awkward than people think. To your point, we’re over assessing the risk. Second, the other side almost always welcomes the overture. They don’t think it’s weird. And so I do think that there is some pretty good evidence, and we look at regret and what people regret over time, to have that bias for action. To speak up, to reach out to that friend, to ask somebody out on a date to sort of be a little bit more risk prone than we might naturally be. Because over time, what you’re going to regret is not doing that stuff.

Matt Abrahams: So first, Dan, you could have collected all of those regrets just by talking to me. I’ve got about 25,000 myself. So I, yeah, I could have saved you time. I really see in my own work and in the work of others that I know who help people feel more confident speaking that virtually everybody after the fact, after they’ve taken that risk, say, it wasn’t as bad as I thought. And the rewards far outweighed my concerns. So I just wanted to echo what you said there. And yet, we are often burdened by our fear of that risk so that we end up ultimately regretting what could have been. And I hope everybody takes a moment to think of an upcoming situation where you might be hesitant because you’re afraid of the risk, and take it from Dan Pink, go do it. It is worth it. In terms of your communication.

Dan Pink: I think there’s an important lesson here. It’s like, just have that slight bias for action. You know, Nick Epley has researched about, no one thinks that talking to strangers on a train. They think that if you say, if you go up to somebody on a train, are they going to welcome the overture? And the view is like, no way, they’re going to hate it. I’m going to hate it. It’s going to be totally awkward. And that when he did research in the Chicago public transportation system, he found that the people who were on the end of the overtures said that was kind of an interesting conversation. I’m glad that person reached out. The person who was instructed to do that said that was way less awkward than we think. So bottom line here is just have a slight bias for action. I have found in his regret research, especially this emotion of awkwardness, is a paper tiger push through that feeling of awkwardness in any dimension of your life. And, and as you’re saying from the people who you’ve worked with, when you get to the other side of that, you’re typically going to be fine.

Matt Abrahams: Absolutely. And awkwardness is a big impediment to communication. And if we just try it, we often find it’s not as bad as we thought. In your book, when the scientific secrets of perfect timing, you give a lot of advice on how to maximize our motivation and take care of ourselves in this incredibly fast paced always on world that we live. What are two bits of advice you might have for us for how to thrive and sustain ourselves?

Dan Pink: Well, I guess the first one would be, once again, the all like research base. We have some pretty good evidence that our cognitive abilities do not remain constant over the course of the day. They change, they change in material ways. And so being conscious and intentional about doing the right kind of work at the right time of day can make a huge, huge difference. And unfortunately, we’re often very intentional about what we do. We’re intentional about how we do it and who we do it with. But when it comes to when we do stuff, we’re not intentional and we should be because it actually matters. The second thing that I would say is take more breaks. Initially, in that book on timing, I was going to write about maybe two pages on breaks in the chapter on this hidden pattern of the day. And there was so much research and so good research that I ended up writing an entire chapter on breaks.

And what we should be doing, it’s a reframing of sorts. We should be thinking of breaks differently. We should be thinking of breaks as part of our performance, not as a deviation from our performance. We have been sold a bill of goods by the Puritans who said that the only way to get more work done and better work done is to power through. And that when you power through, that’s also morally virtuous. That’s complete nonsense. What we know from many domains is that professionals take breaks. It’s not let amateurs take breaks and don’t, it’s the exact opposite. Professionals take breaks, amateurs don’t take breaks. So be intentional about your breaks and where you can, the best kinds of breaks are when you’re in motion, when you’re outside, when you’re detached from your phone or even from your work, and often when you’re with somebody else. So even taking like a 15 minute walk break every afternoon can be powerfully helpful in sustaining your intellectual and, uh, physical energy.

Matt Abrahams: I think taking a break in conversation and in the work we do, very, very important. And this notion of timing of when things work best for you is really powerful. We’ve had Baba Shiv, who is one of our faculty here at Stanford’s Business School who has studied this, and it’s fascinating that we are more collaborative and creative at certain times of the day, and it’s better to try to harness the, the type of activity we do that fits with those rhythms and absolutely taking breaks, taking time to disconnect can be really, really powerful. So Dan, before we end, I’d like to ask you the same three questions I ask everyone who joins me. And I am really curious and excited to hear your answers. Are you up for these?

Dan Pink: Yes.

Matt Abrahams: Question one. If you were to capture the best communication advice you ever received as a five to seven word presentation slide title, what would it be?

Dan Pink: Decide the promise you’re making, then deliver.

Matt Abrahams: Okay.

Dan Pink: Okay. And then I’ll unpack that very quickly. So, years ago I was working on, back in the old days when there were magazines, I wrote a lot for magazines. And, you know, I’d write these fairly long feature stories, 4,000, 5,000 words. And at one point, you know, I was stuck on something. I, I submitted a draft, it was terrible, and I was really stuck. And my editor said to me, it’s like, okay, I know the problem here. You don’t know what promise you’re making to the reader. What promise are you making to the reader in this piece? And I was like, what? And that was really enlightening to me. I think hard about that. And what I’m writing when I’m talking is like, what’s the promise I’m making to the reader or the listener? And am I fulfilling that promise? So, decide the promise you’re making and then deliver.

Matt Abrahams: I think that is really powerful. Know your goal, know your intention, and then act on it. Very good. You know, so many people and you’ve had such a fascinating life. Question number two: Who is a communicator that you admire and why?

Dan Pink: Okay, so I think my choice is not somebody I know. Not only is it not somebody I know, but it’s not somebody who’s alive. And it’s somebody who might not be a somebody. I was thinking about this during my walk. I took a walk right after lunch and before I did this talk with you. And I was thinking, Aesop. When you think about it, Aesop had these parables, these fables, they were probably 150 words long. They have withstood the test of time to put it mildly and they’ve lodged in our brain so powerfully that you can use phrases like tortoise in the hare or sour grapes, or, you know, the grasshopper, and it sticks. And that’s pretty good. So I’m going to vote for Aesop.

Matt Abrahams: You have truly gone old school. You are, you, you have brought up the oldest suggested great communicator, and you clearly have highlighted some things that are important for good communicators, something that’s memorable, being concise, creating something that has the impact.

Question number three, what are the first three ingredients that go into a successful communication recipe?

Dan Pink: Number one, simplicity. Number two, Brevity.

Matt Abrahams: I see what you did there.

Dan Pink: And I’m not even going to use my third.

Matt Abrahams: I know, I saw that. Simplicity and brevity, make it accessible, make it understandable, make it memorable. All very powerful bits of advice and guidance. And Dan, everything you’ve shared with us has been powerful. It has been such a pleasure to chat with you. Hey, thanks. The, the notion of being human and connecting with humans, knowing our purpose, and really understanding our promise and having a bias for action, all of these are really powerful. Thank you so much. I wish you well on your new book, The Power of Regret, and I appreciate your time.

Dan Pink: What a pleasure, Matt.

Matt Abrahams: Thanks for joining us for another episode of Think Fast Talk Smart, the podcast from Stanford Graduate School of Business. This episode was produced by Jenny Luna, Ryan Campos, and me, Matt Abraham’s. Our music was provided by Floyd Wonder. For more information and episodes, find us on YouTube or wherever you get your podcasts. Thank you. And please make sure to subscribe and follow us on LinkedIn.

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