Thought Leadership Series
A Conversation with Daniel Pink: Timing Is Everything
School Administrator, October 2020

Daniel Pink is the author of four New York Times bestsellers.

Editor’s note: The first installment in School Administrator’s Thought Leadership Series featuring prominent book authors captures the thinking of Daniel H. Pink in a conversation with Jill Siler, superintendent of the 1,000-student Gunter Independent School District, an hour north of Dallas, Texas. 

Pink, an author of six books, including four New York Times bestsellers, has had a longstanding interest in the leadership of elementary and secondary schools and education issues. He’s written for several education publications, including School Administrator (December 2012) and served as a keynote speaker at AASA’s national conference in 2013. 

In Siler’s interview, which focused primarily on the author’s most recent book When: The Scientific Secrets of Perfect Timing, Pink talked about transitioning a school system in the midst of a pandemic, circadian rhythms, the value of midday breaks and the essential nature of timing. 

(The Thought Leadership Series in November features author Dan Heath in conversation with Joe Sanfelippo, superintendent in Fall Creek, Wis.) 


Jill Siler: I’m going to jump to your earlier book Drive, which is one of my favorite books. Loved rereading it to get ready for our time together today. But, that whole notion of purpose, autonomy and mastery — I hate to throw the word seminal around, but it really is some of the most foundational work that we use as leaders, even going back to in school. It’s about our “why,” trying to make sure that our teachers have this guaranteed and viable curriculum, that we have systemic structures in place, but also that they have that artistic act in their classroom to do what they want with that. And, then, just mastery. 

One of the biggest challenges that I saw as a superintendent as COVID hit and we completely transitioned our entire systems of teaching and learning to remote was that our teachers lost that whole foundation of mastery. Certainly, they had digital tools beforehand. Certainly, we have incorporated them. But, to completely transition to a remote environment was absolutely brand new. 

I saw that frustration and I knew that there was so much playing into it obviously — pandemic and fear and all of those things — but in the end, what I really sifted out was that they lost the mastery and what a struggle that was. What are your thoughts about when people are faced with that steep curve of learning in a position that’s new to them, or for whatever reason, where they kind of lost their mastery, their whole foundation has shifted?

Daniel Pink: That’s a great question. I don’t think there’s a singular answer to it; there are probably multiple ways to think about it. So, one way to think about it is to challenge the very premise: Have they truly really lost their mastery? Or, are they simply taking something they’ve mastered and doing it in a slightly different way?

I do think that there’s a deep structure of effective teaching and a deep structure of values of great education that transcend the medium in which it’s delivered.

So, a way to look at it when people say, “I’ve completely lost my mastery” is to push back and say, “Have you really? I’m not sure that’s actually true.” Great teaching is about taking a student on his or her own terms. Great teaching is about being impactful. Great teaching is about having high standards. And you can do those things remotely as well as in person. That’s one approach.

Another approach to it would be almost like the ancient philosophy of stoicism, which is just to lead into it and to say, “This is new.” Look at this not so much a daunting problem, but rather a meaningful challenge and in some ways, I’m being intentionally provocative here, actually to be grateful for it. Say, “Thank you. Wow. Now, I’ve got to learn a new way of doing something. Thank you, stoic gods, for giving me this challenge.” So, that’s another way to go into it. 

I do think that there are certain educators who are going to lean into that and say, “Wow, this is cool. This is an interesting problem to have. This is an interesting challenge for me to have.” 

Jill Siler leads a 1,000-student district an hour north of Dallas, Texas.

 The third way, and this is where superintendents come in as guides and coaches, is when people are struggling, go for small wins. I think about elementary school as having the biggest challenges here. Imagine you’ve been a great second grade teacher for 15 years or 20 years and all of a sudden, your little 7-year-olds are boxes on a screen rather than faces in a classroom. That’s not anything you’re going to be great at immediately. It’s very hard. What I would do at the leadership level is to look for small wins. Really try to give people as much feedback as you can. Try to find small wins and bright spots to help them along. 

My guess is that if you go in with that repertoire of strategies, whether it’s pushing back on the idea that you’ve lost your mastery, whether it’s inviting the challenge rather than seeing it as an inherent trouble, and do small wins — some combination of those is going to be effective in particular cases. 

Siler: I love that. You know, what our teachers did was nothing shy of miraculous. And, I would say leaders across the system, absolutely. But I think that because they’re teachers, they love their kids and they love being able to meet their needs. I take it back to this: I speak Spanish, but if you were to put me into a Spanish-speaking country right now, there would be a struggle. And I think that’s what they felt. It was just that we dabble in this and now it’s our every day. We’re not digital natives, if you will. And, so, I loved what you talked about. 

Pink: Let me go back to that, Jill. Let’s say that someone has a passing knowledge of Spanish. You throw them into a Spanish-speaking country. For the first week they’re there, they’re going to be stumbling. They’re going to be going into the restroom of the wrong gender. They’re going to be ordering a piece of cake when what they really wanted was a slice of pizza. So, they’re going to be making those kinds of mistakes and they’re going to feel ill at ease. The second week, they’re going to make fewer mistakes, get their footing. The third week, they’re going to make even fewer mistakes and really find their footing. 

There are all kinds of challenges in this shift to remote learning. At some level, for many things, it’s just inherently a poor substitute. But, my experience, anecdotally, is that most teachers have actually risen to the challenge. 

Siler: I agree 100 percent. 

Pink: And, what’s fueling their mastery, what’s fueling their willingness to climb up that mastery curve, is their sense of purpose. 

Siler: Absolutely. What a great statement. I hear that gratefulness, too. When I’ve done our end-of-the-year surveys and check-ins, they have said that while it was painful, the growth that they experienced was tremendous. It is going to serve them well in the future. 

So, we’ll shift from Drive to When. One of the things I was just thinking about as I was reading this book was it seems in my journey as a leader, I’ve shifted on this pendulum. In the early days, it was really focused on the what. What are we supposed to do as leaders? And, part of that was that I was young. Part of that was just the major works of the time in terms of things I was reading. And, then, of course, more recently we’ve shifted to the why in Simon Sinek’s work, in your work with Drive. 

When I picked up this book on when, it just was really enlightening. So, my question to you is what made you dive into this? I love how you stated that we simply don’t take the issue of when as seriously as we take the issue of what. So, what is it you expect to learn, and why was when so compelling to you? 

Pink: Purely for personal reasons. You have a glimpse of my life here, Jill. You’re literally looking into my office, which is a tiny garage that’s been refurbished. My house is right there, so, for years, I would come out to this office and do my work. And, I would have to decide when to do stuff. It hit me at a certain point that my decisions about when to do stuff were pretty ill-informed. I was making these decisions based on intuition and guess work. And it got me frustrated because I’m pretty intentional about what I do. I’m pretty intentional about how I do it. To your point, I think I’m more intentional about why I do certain things, but I was making these when decisions in a completely sloppy way. That frustrated me. 

I looked around for guidance; okay, someone’s got to be able to give me some help, some instruction on how to do this. And to my surprise, that guidance didn’t exist. 

That got me curious. I started looking around and I realized there was a huge amount of research. It was very unwieldy because it was in so many different disciplines. I said, “This is a book I’d like to read, and since nobody’s written it, I’ve got to write it in order to read it.” 

Siler: There were so many relative topics in When that directly related to schools. I want to focus on two: the basic premise of when we do things, which you just alluded to in that response, and the power of restorative breaks and how both relate to school. 

Starting us off, you shared that all human beings don’t experience a day in precisely the same way; that we all have our own circadian rhythms that impact the way we should do certain tasks, whether analytical, insightful, or when to make the best decision. So, tell us a little bit about that. 

Pink: Here’s what we know, in general. Most of us move through the day in three stages. There’s a peak, there’s a trough, there’s a recovery. Most of us, about 80 percent of us, move through the day in that order: peak early in the day, trough in the middle of the day, recovery later in the day. 

However, about 20 percent of us have an evening chronotype. That is, we’re night owls, meaning that we naturally wake up late and go to sleep late. Most educators are not night owls. There’s actually some evidence of self-selection out of education — certainly elementary and secondary education — for people who are night owls because you all start school so early. If you’re a night owl, getting to your job at 7:20 a.m. is painful. 

So, what we know is peak, trough, recovery, 80 percent, in that order. For owls, it’s different. Owls get their peak much, much, much, much later in the day — so, evenings, late evenings. 

Here’s what we know. During our peak, that, which again, for 80 percent of us is early in the day, that’s when we’re most vigilant; we’re able to bat away distractions. That makes the peak the best time for, as you say, analytic work. So, that’s just work that requires heads down, focus and attention. Writing a report, going over strategy, analyzing data and that sort of thing. So, most of us do that type of work better early in the day rather than later in the day. 

During the trough, early to mid-afternoon, is a terrible time of day. That’s not just folklore; there’s a pile of evidence backing that up. So the trough is when we should be doing more of our administrative work. And, when we have to do other kinds of important work during that period, which our conversation now is an example of, there are things that we can do, which I’ll tell you about in a moment. 

Here’s my cup of coffee. Even though it’s a 101 degree heat index, I took a walk around the block before this conversation because I didn’t want to come into this conversation at this terrible time of day. 

And, then, during the recovery period, which is for about 80 percent of us late in the afternoon, early evening, our mood is up. That makes it a good time for things that require certain kinds of mental looseness: iterating new ideas, brainstorming, solving non-obvious problems. 

What the research tells us at a big, broad level is that where we can, we should be doing our analytic work in the peak; our administrative work in the trough; and our insight, iterative, creative work in the recovery period. What we also know is that there are big differences in performance. This is not a nicey nice, hey, we might feel a little bit better, we might self-actualize a little faster if we match up our mental acuity with the time of day. There are big differences in performance. Our brain power doesn’t remain constant over the course of the day. 

So, if you go into your work as a leader, if you go into your work as a teacher, if you assume that students’ brainpower remains constant over the course of the day, you’re going to make some pretty big mistakes. But, if you recognize that our brainpower changes in mercurial ways, the best time to do something depends on what you’re doing, you can begin to make changes in your daily schedule that will allow you to perform better and, in most cases, feel better. 

Siler: I love that. And, you go deep when it comes specifically to teenagers. You talk about young people undergoing that most profound change around the time of puberty. What did that research lead you to believe about when students learn best? 

Pink: It goes back to chronotypes. We have this distribution: About 15 percent of us are true early morning people. Twenty percent of us our owls, hard-core evening people. About two-thirds of us are in the middle, but we kind of lean a little bit more toward larkiness. But that doesn’t remain constant to our lot. 

As every parent of teenagers knows, as every middle school and high school teacher knows, around the age of 13 or so, kids have a big mood for lateness. They naturally get up later, they go to sleep later. One other consequence of the timing research is overwhelming evidence that middle schools and high schools typically start too early. This is one of those things where the evidence is so overwhelming, it’s not even a close call. You have the American Academy of Pediatrics a couple of years ago saying, “Do not start school for teenagers before 8:30 in the morning.” It is contraindicated by everything we know about teenage biology and yet typical start time for teenagers in this country is a little bit after 8, which means there are plenty of schools starting way before then. Kids who are taking buses to school rather than walking — those kids are getting on buses ridiculously early. 

Siler: Not to mention extra-curricular activities, which start even before then. 

Pink: Right. If you have some kids who are, say, swimmers. So, it’s pretty clear that school starts too early for teenagers. And, if we push back the start time for middle schoolers and high schoolers, we’re going to see better performance. School districts that have done this have seen higher test scores, less absenteeism, higher graduation rates. There’s a big study in the western United States, not in the southwest United States, but western United States, like Wyoming and Colorado, showing a big decline in teenage traffic accidents by pushing back the start time. There’s evidence from some districts in North Carolina showing that pushing back the start time is actually a cost-effective education intervention. That is, for a low cost, you can boost performance. 

One of the things we see in a lot of this research on the effect of time of day and timing of student performance is that when we do it wrong, the students who suffer the most are the least-advantaged kids. And when we do it right, the students who benefit most are the least-advantaged kids. So, the status quo hurts lower-income, less-advantaged kids the most. Changing the status quo helps them the most. So, there’s an equity issue in it as well. I mean, it helps everybody. Being smarter about the when of education. But it really does help the least-advantaged kids the most. 

Siler: It was fascinating to read about and fascinating to hear you talk about it. 

Pink: The book is now a couple of years old and there’s been some movement in school start times since then. California Governor Brown vetoed legislation that would have pushed back the start time. Governor Newsome got that through. There have been other changes, district by district, so there’s been some movement there. But, still, it’s lagging behind. 

There are all kinds of things for which superintendents have to make the tough calls. Rarely is it, “Let me assemble the evidence, let me assemble the arguments. In some cases, we have imperfect information, and I think, based on this imperfect information, that option A is slightly better than option B, so, let’s go with option A.” That’s typically the kinds of decisions superintendents are making. 

This one is actually clear cut. The evidence for pushing back start times is overwhelming. This is not a case of imperfect information and competing evidence. This is a case of a lot of information, a lot of evidence, all of which is pointing in one direction. 

Daniel Pink’s books lend research-backed insights on motivation, leadership and the science of time that appeal to educators.

Siler: You talked a little bit in your research about how students who took a 20- to 30-minute break to eat, play and chat before a test tested better. What were some of the compelling things you uncovered around the benefits of breaks for children and for adults? You talked about the break you took right before coming into this interview. Share with us a little bit about that. 

Pink: It’s another really important point. One of the most compelling studies comes from Denmark. Students there take standardized tests. But a typical Danish school has more students than computers on which to take the tests. So, the students are randomly assigned to take the tests at different times of day. Some take the test early; some take it later. A massive study — it analyzed 2 million Danish test scores — found that kids who took the test later in the day scored as if they had missed two weeks of school. Just random assignment of these kids. So, that’s troubling. 

If you have these two kids, and one takes the test at 9 in the morning and the other takes the test at 2 in the afternoon, the kid at 2 in the afternoon scores as if she’s missed two weeks of school. That’s troubling. 

You also see it in an important piece of research out of the University Chicago looking at the Los Angeles Unified School District. As we were talking about earlier, LA Unified is going completely virtual. Another ginormous school district going completely virtual from the get-go this year. The students who took math in the morning did better, got better grades, scored higher on statewide tests than kids who took math in the afternoon. So, again, our brain power isn’t constant over the course of a day. When we do stuff matters.

Breaks can be an antidote to some of these problems. For instance, the fact that you just mentioned comes from the Danish study where they said, “Wait a second, there are these differences of performance based on time of day. This is not good.” That same study found that if you give these afternoon test takers a 20- to 30-minute break before the test, they had a snack, ran around a little bit, they scored a little higher. 

What this tells us, to actually answer your question after that lengthy buildup, Jill, is that we aren’t thinking about breaks correctly. We think about breaks as a deviation from learning. Breaks are part of learning. That, to me, is the takeaway from all of this research. Breaks are not something that we do when we’re not learning. Breaks are part of how people learn. And that’s something that I didn’t fully understand until I went through this research. 

Even in performance among adults, even if you look at labor negotiations, we think of breaks as a concession that management makes to labor so that they don’t have to work. But, in fact, we’re thinking about it entirely wrong. We need to be thinking about breaks the way that athletes think about breaks. Athletes think about breaks as part of their performance. Athletes would never train and refuse to take a break because they know that that is counterproductive. What we know from students is that breaks — and certain kinds of breaks especially — increase and enhance learning. Plain and simple. 

One of the things that you see, I think it’s abated a little bit now, is there’s been a move to reduce recess, get rid of recess, in the name of rigor. That is a terrible idea. It goes against the science. The science tells us is that, if you want people to learn, give them breaks. If you want people to perform at a higher level, be productive, contribute, give them breaks. It’s the same reason that we know, overwhelmingly, that if we want teenagers, especially — any human beings— to learn, sleeping is one of the great learning enhancers. I’ve told this to my own kids when they were in high school studying. 

Jill, what kind of research do you have in your school district?

Siler: I’m in the elementary, and you read these things and part of it is just affirming that, yes, we’re doing good things. And, then part of it is convincing, like, I need to rethink that. 

Right now, our recess and our lunch are side by side, and that was one of the things I really thought about. There’s movement and, of course, we have PE and we go to specials and do all those sorts of things. But that was one piece that we do for a very purposeful reason: to give teachers time to plan. But then, when I thought about that in light of the research, it definitely made me rethink how we do things. 

Daniel Pink says the when is just as important as why and how of education.

Pink: I really do think that teachers need more breaks. Compared to other white collar professionals, teachers get very few breaks. So many teachers I know tell the story about thinking through at the beginning of the day when they’re going to be able to go to the bathroom, let alone when they’re going to be able to take a walk or do something like that. 

And superintendents, because of the nature of your work, you’re just running around like crazy people all day. On the way to work, you’ve already been notified about three fires you need to put out that day. When you get to work, there are five more. By 10 o’clock, you’ve got a dozen fires you need to put out that day. And then, the break always falls off. But, if administrators, superintendents supported breaks, they’d be better off, too. 

Siler: I’ve noticed it the most during COVID because this is what I do all day. From 7 in the morning until 7 at night, and then sometimes I’ll get up and go, “Man, this is only the second time I’ve literally stood up today.” That is not good. 

Pink: No. But, one of the things I do is I’ll set alarms to take a break because if it’s not scheduled, I won’t do it. I’ll sit here and say, ”Oh, let’s do another Zoom call or write another paragraph.” 

Siler: I want to shift to leadership a little bit. As a student of leadership, one of my favorite sections in this book was talking about the importance of the boss. You talk about it as someone or something above and apart from the group itself to set the pace, maintain the standards and focus a collective mind. 

I love the story that you told about the choir director and the coxswain, the rowing crew chief. It really made me dig deeper in my own thinking when you talked about the rowing team, that their speed depends on someone who never touches an oar. And the choir — their sound hinges on someone who doesn’t sing a note with them. 

What did you see in both the choir director and the coxswain that made you look to them as leaders that cultivated their success? 

Pink: If you look at how groups synchronize in time, which is important, it turns out that having that leader, having that clear standard setter, is actually really, really important because that person plays a somewhat unique role. 

And again, you quoted what I think is the most germane part of that, which is that those people aren’t doing the work, they basically are setting the pace, letting people know how they’re doing, giving people coaching: when to slow down, when to speed up, when to try harder, when to relent a little bit. But they’re actually not doing the work. They’re someone whom the other folks on the team can look to for guidance. They’re setting the pace, setting the standard, but they’re not doing the work. 

I think what is so interesting, metaphorically, is that in both cases, the leader and the people being led are facing different directions. To me, it’s an interesting metaphor for a certain kind of leadership. It’s about high standards, it’s about setting the pace, it’s about being visible, which I think is super important. And also, related to that is establishing a sense of belonging, that the leader’s job is to create the conditions for a sense of belonging, to nurture that as it’s going on among the group itself. 

Siler: I love that. And that has so much carryover to the school setting from within the classroom, in terms of creating that culture and setting the pace, to an entire campus, to my work as a superintendent, working with the entire district. 

Pink: But, also, you probably see it, there are invisible leaders and visible leaders. And the thing is, when leaders are invisible, it’s not as if people forget about it. They say, ”Hm, I wonder why she isn’t visible. I wonder what she’s hiding. I wonder what nefarious things are going on.” And to me, you might as well just be transparent, open and visible. A big part of it is that visibility. The metaphor of both the coxswain and the choir master being in people’s line of vision is a really powerful lesson. 

Siler: You talked about transparency. I think one of the things that we struggle with as leaders is that we want to give off this notion that we are confident, that we are strong. In your book, you talk about the power of storytelling to bring groups together. One of the things you say is that the stories your group tells should not only be tales of triumph, but stories of failure and vulnerability which also foster this sense of belongingness that you’re talking about. How do you reconcile the need for leaders to exude that confidence and strength that we know is needed, but also the power that can come from being vulnerable and talking about failure? 

Pink: Yeah, that’s a tough one. You got it exactly right that you’re on a balance beam and there’s not a lot of room on either side. And I would argue, again, based on research done by folks like Susan Fiske and Amy Cuddy, that that balance beam is even narrower for women leaders than for male leaders, which we can get to in a moment. 

If you have no outgoing clarity and it’s all about internal transparency, they’re going to say, “Okay, this person isn’t all that great, and I don’t even know what they’re doing.” If you have clarity going only in this direction, no transparency in that direction, it becomes like Wizard of Oz, like, what’s behind the curtain. But, if you have both ways, people say, “Wow, this person has a clear vision, but this person also is humble, this person is willing to listen to contrary opinions, this person is willing to be transparent, this person is an authentic human being.” Then, I think you’ll have a fighting chance of combining that outward clarity with that incoming transparency. 

Now, I want to talk about the conundrum for women, because it’s a big deal. And again, Susan Fiske at Princeton did a lot of this work. When we think about leaders, what people want, in general, are leaders who are warm and leaders who are competent. Okay, so we want warmth and competence. The thing is that men are more easily perceived as both warm and competent at the same time. 

It’s a bit oversimplified, but we can reduce this issue to a two-by-two matrix. So, if you have this two-by-two matrix, you have warmth and competency, right? So, someone who is competent but not warm, we think of as kind of like an effective jerk. And, someone who is warm but not competent is sort of like a nice dope. Right? And, someone who is neither is just a terrible person. 

What we really want is the good leaders to occupy this upper right quadrant, where they’re warm and competent. But there are gender issues, as you probably know. People can get their mind around the idea that a guy, a male, particularly a straight white male born in America like me, can be both warm and competent at the same time. But with women, people say there has to be a tradeoff. If she’s warm, she’s not competent. If she’s competent, she’s not warm. And they’re unwilling to perceive women being in that category that is the most effective. So, it’s known as a double bind for women. It’s a big problem, and it’s a problem that, I think, the onus is on men to get over that stereotype. 

I think we’re getting slowly there. Women leaders can be perceived as inhabiting that upper right-hand quadrant, it’s just that the path there is steeper than it is for someone who looks like me. 


Siler: AASA’s School Administrator magazine did a great series of articles about women in the superintendency and how difficult it is to get to that level and why they’re not occupying some of the highest roles. In Texas, at least, what we’ve seen is that the longevity of females in their current roles outweighs males. And, there’s a lot of questions about that, like why don’t women move on to larger districts? Even me — this is my ninth year in this role. In these eight years, I’ve been able to establish both that competency and that warmth. It is difficult when you go into a new community to establish yourself in both of those ways. That’s really interesting to think about. 

Pink: I think there’s another hypothesis, too, about women’s longer tenure, which is that men believe bigger is better and women believe better is better. 

Siler: I like that. 

Pink: That could be a simplistic way of looking at it, but you see a little bit of that in the research on male and female entrepreneurs, where male founders tend to lead companies that are bigger than female founders. People say, “Well, what’s going on? Is it access to capital? What is it?” 

There are all kinds of reasons, but one of the issues is that women say, “I just want to run a great business. I want to run a great business that delivers great products and services that delight our customers, that provides great jobs for people. My ambition is not to build the biggest business. My ambition is to build the best business.” 

I never want to undercut outright sexism, but I think that there’s another factor here, which is men’s sort of obsession with “I’m more legitimate if I’m running a big operation rather than a smaller operation.” 

Siler: Very interesting. So, your final words in this book, and I still have a couple more questions, but your final words in this book, When, was one of my favorite conclusions I’ve read. 

Pink: Well, thanks. 

Siler: So often, you can try and tie that knot, but it was beautiful — almost a poetic declaration of what you used to believe versus what you now believe after writing this. You close with this line: “I used to believe that timing was everything. Now I believe that everything is timing.” As leaders, there’s so much to think about. What we do, why we do it, how we do it, who we raise up to work with. What’s the biggest aspect that you think about when it comes to when? 

Jill Siler is in her ninth year as superintendent of Gunter Independent School District.

Pink: I’m going to start abstract, but I think it’s having the ability to think in temporal terms — just adding when to your quiver. So, you have superintendents, you know, they are these superheroes and they have this quiver of arrows. There are medieval superheroes and they have a quiver of arrows around their back. So, they’ve got the what we’re going to do, or we’ve got the who — we’re going to hire great people. Increasingly, they’ve got the why. We’ve got the how through investments in teachers’ professional development. And I just want to add the when arrow to their quiver because it’s going to help them strategically, because of the following. 

All of the people they’re interacting with, from the students, staff, to the board, to the teachers — they are all temporal creatures. Human beings are temporal creatures. As I explained in the book, it’s not like we have a biological clock. We have biological clocks in every cell in our bodies. At some level, we’re walking time pieces. 

The nature of superintendents’ work is very temporal. Think of all these recurring cycles. Another school year, the school year has a beginning, school year has a middle, school year has an end, school year has these temporal landmarks along the way. You’ve got these temporal creatures that you’re dealing with, all of whom are moving through time. You have to have that when arrow because you’re going to be a more fully equipped leader that way. 

I’m not saying that when is more important than what or who or how; but I think it’s as important. Superintendents and other education leaders are going to be more effective, better able to make a contribution to the world, better able to lift the lives of all these kids they’re serving if they add that temporal dimension to their arsenal. 

Siler: One of my mentors went through the Breakthrough Coach training, which is trying to relook at how you shape your day, be out on campuses more often. One of the concepts that came from that training was whether your calendar reflects the kind of leader that you aspire to be. For me, what this conversation is shifting me to think about is when I’m choosing to do things reflective of the value of the work that I’m trying to accomplish, and I think that’s a big question for leaders to tackle. 

Pink: That’s well said and a really brilliant point. Leaders can do that kind of audit on themselves, like, “Let me look at my calendar for the last two weeks. Does this reflect who I am and who I aspire to be? And is this the type of service and leadership that I aspire to?” I do that myself, periodically. And, a lot of times, we fall short. 

Siler: So, final question, and this one is not focused on any book. You can draw from all of things you’ve written in all of the years. But, as we have this interview mid-July, in the midst of the COVID-19 pandemic, school leaders across the country are trying to make these massive decisions about when to start school, how to start school, how to balance the data from health professionals with their own desires of their own communities. We’re trying to lead within the various constraints of state and federal leaders, and it’s a time of great uncertainty that’s fraught with conflicting information and that’s underscored by fear. We have all of these things going on. From this massive body of work that you’ve been involved in around business and behavior and creativity, what advice would you have for leaders to lead during this time? 

Pink: It’s a tough time to lead, so I don’t want to be glib and say, “Oh, just do these three things and everything will work out fine“ because I don’t believe that. I do think that there are some guiding principles, some of which we have talked about. 

Number one, in this moment, I think that there is a premium on care. And what I mean by care is: Do your constituents — whether it’s, parents, teachers, board members and, especially, students — do they know that you care and that you have their backs? That’s incredibly important, and that’s something that you show; it’s not something that you say. 

Again, some of the interests are going to be pitted against each other a little bit. It’s not going to be perfectly resolvable. But I do think there’s a premium at this point. People are looking for leaders who say, “I care, I’ve got your back, I’m going to try to protect you from harm.” And, I think that is unique to this particular moment. That’s one thing. 

The second thing is — and these are more broadly applicable — a combination of transparency and humility. You know, opacity is never a good idea in these kinds of situations. Transparency is not perfect, but it’s better than the alternative because when you’re not transparent, people are going to start wondering what’s going on behind those closed doors. And what they’re wondering is always way more nefarious, what they’re suspecting is always way more nefarious than what’s actually going on there — which is flawed people with imperfect information trying to do the right thing. 

So, open up the curtains. Open up the doors. Be as transparent as possible. Also, I think that there’s a paradox to humility. We think of it as weak, but it’s actually quite muscular. Sure, we want leaders to be confident, but it’s possible to be both confident and humble at the same time. So, there are going to be lots of times in this moment when leaders need to say, “I don’t know. What do you think?” That’s one of the most important things that leaders can do. So, a combination of transparency and humility. 

The other thing that I’ve been thinking about, and I’m trying to do myself and encouraging other leaders and other people to do, is to do a little bit of time travel. And, what I mean by that is this: Travel in time, five years from now, 10 years from now. You’re looking back on this moment — what did you do that you’re proud of? Did you complain, did you cut corners, or did you step up, be bold, try to do the right thing and improve your part of the world? I find that that exercise can really focus people’s minds.

I do that myself at a smaller level. Again, my job is so much easier than a superintendent. I say, “Okay, do I want to look back and say I spent this pandemic complaining about not being able to go outside, and hate scrolling on Twitter, and watching old sports highlights?” Or do I want to say, “I used this time to do some small acts of good for my community, to take care of my family, to make progress on another piece of work, another project that I keep putting on the back burner all the time?” I think that that, at sort of a high level of abstraction, is a really useful exercise. 

Siler: Great. I am so thankful for your time today and just for the insights you shared.

Pink: My pleasure.