Adjusting the Dial on Leadership: A Conversation with Simon Sinek

Type: Article
Topics: Leadership Development, School Administrator Magazine

August 01, 2021

Thought Leadership Series
Simon Sinek
Simon Sinek, author of the bestseller Start With Why, says when organizational leaders are authentic, people are drawn to them for who they are with a willingness to follow. PHOTO COURTESY OF THE NORDIC BUSINESS FORUM

In this eighth installment of the School Administrator’s Thought Leadership Series, we feature the insights of Simon Sinek, a British-born inspirational speaker and author of multiple best-selling books, including Start With Why, Leaders Eat Last, Together is Better, Find Your Why and The Infinite Game. Sinek’s first TED Talk in 2009 rose to become the third most-watched on with more than 40 million views and subtitled in 47 languages.

Sinek recently was interviewed by Charles Dupre, who is retiring this month as superintendent of the Fort Bend Independent School District in Sugar Land, Texas, after eight years. The two discuss Sinek’s concept of “infinite games” — where players come and go, the rules are changeable and there is no defined endpoint — in relation to school system leadership during the post-pandemic and how our “why” can help us formulate our “just cause.” The author shares strategies for bringing authentic diversity, equity and inclusion to the organization and emphasizes the importance of superintendents taking care of each other.

The interview has been edited for clarity and length.

CHARLES DUPRE: Now that we are more than a year into the pandemic, superintendents and school leaders have been operating in crisis management mode. We have been managing virtual learning environments and navigating the politics of whether or not students should be learning face to face. From personal experience, I can attest that playing the infinite game has been exceptionally challenging, if not impossible. So, as we begin to move into the post-pandemic era, what suggestions do you have for organizations as they attempt to return to “normal” and resume efforts toward achieving their established “just cause”?

SIMON SINEK: Well, you talk about it being hard to play the infinite game during the pandemic, and when crisis looms, sometimes, I think we lose that long-term perspective because we just need to keep the lights on, you know? But I think one of the things the infinite mindset helps with, especially in times like this and as we determine what returning to normal looks like, is understanding that none of this stuff is an event. It’s a process. That there’s no such thing as “getting it right.” There’s going to be a series of decisions, and some are going to be right, some are going to be wrong, some are going to be right at the time and then they’re going to change.

One of the things I think crisis does is provide an opportunity to re-evaluate everything. Before, it was just too disruptive to re-evaluate everything. Even if you knew things needed to change in education or in your school, you just couldn’t do it. Crisis created the disruption for us. Which means we have an opportunity to put the pieces back in a different shape.

Now to the question of “what does it look like when we go back?” I think there are two answers. For those who saw the disruption as an opportunity, I hope their pursuit of constant improvement continues and that they built a degree of trust with teachers and parents to continue to tweak the system — looking for little improvements here and little improvements there.

I hope the systems that didn’t take advantage of the disruption can at least say, “Whoops, we missed an opportunity to actually make some improvements that probably should have been made a decade ago, but we commit to now coming back and looking for new ways to tweak the system and make constant improvement.” I hope this crisis has at least served as a catalyst for even, slow change.

DUPRE: You have talked about how important it is for educators to keep tweaking and implementing minor refinements based on what we learned during the pandemic. Is there a way to capitalize on major changes made during the pandemic by jumping into the deep end and learning as you go, or is it better to pull back and then press forward more slowly?

SINEK: The answer is “yes.” Two thoughts come to mind.

First, change and growth need to be treated like a dial rather than a goal. Consider a retail establishment that wants to grow its business quickly. They’ve set a goal of opening 200 stores this year. Nothing wrong with that. It is like a school saying, “We’re going to convert every kid to one to one. We’re going to take all that budget for computers in the classroom and we’re going to figure out a way to give computers to kids who don’t have access to computers at home.”

Wonderful goal, right? But the company that’s trying to open 200 stores in one year is opening them so fast, they realize they’re not hiring properly and they’ve left no time for training. So the experience for the customer walking into the store is abysmal. By the time they get to 200 stores in another year, they’re going to end up closing them real quick, too. To avoid that, it’s best to say, “We’re going too fast. We bit off more than we can chew, so we’re just going to change the dial and open 20 stores, and we’re going to do that properly. Then we’ll worry about the next 20 stores — or maybe 50 stores — next year.”

We have to look at all of these ambitions as dials rather than goals or absolutes. It doesn’t matter if we establish that we’re going to get every student a [laptop]. During the process, new problems will be revealed. So the question is, “Can we adjust the dial so that we’re doing it right?”

Second, the way innovation really works, versus the way people think it works, is you don’t start by defining what your product ambition looks like then try to build it outright. For example, we want to redo our website. We identify all the whiz bang features we want our website to be able to do. It’s going to be an incredible new website, and we start building it, but here’s the news flash: It will never work as planned. So we end up spending all our time trying to fix it.

Charles Dupre
Superintendent Charles Dupre has applied the leadership thinking of Simon Sinek during his time as head of the Fort Bend Independent School District in Sugar Land, Texas. PHOTO COURTESY OF THE FORT BEND INDEPENDENT SCHOOL DISTRICT

Here’s how innovation actually works. We have the ambition to develop that whiz bang, amazing website, but we don’t actually try and build it. We say, “What’s the cheapest, simplest thing we can do that will achieve the highest probability of success?” We’re going to start there. One little step toward that ambition, the cheapest, simplest thing we can do with the highest probability of success. Check. Done.

Again, we ask, “What’s the cheapest, simplest thing we can do to improve the thing we just did, with the highest probability of success?” And what you find if you take that ladder approach is that you end up making up something that’s way better than what you planned. Asking the question about the cheapest, simplest thing you can do with the highest probability of success won’t completely solve every problem — it’s not supposed to. But the ladder approach is much lower risk.

One of the things I recommend is, instead of trying to sell the farm, just try and sell the chicken. Instead of trying to convince a board or a parent group that we have to buy this farm, sell them one chicken, and then another chicken, and before you know it, you’ve got a farm.

DUPRE: Many reading this interview may have read your book Start With Why and might be wondering if their “why” is the same as a “just cause,” which is a major component of The Infinite Game. How do the why and just cause differ?

SINEK: They’re different animals. A why, ostensibly, is an origin story. It’s where you come from. A just cause is about the future, it’s where you’re going. A why is objective. To understand your why, to articulate your why is a process of discovery. So, for example, every single individual or organization has a why. You know, we all have origin stories. You and I have our own unique whys that are the sum totals of how we were raised.

Our personalities come from our world view; our values come from the experiences we had when we were kids. Our why was fully formed, probably by our mid- to late teens, and we are who we are, and the rest of our lives offer us an opportunity to live in balance with that why or not. When we are authentic, people are drawn to us for who we are, and when we are “inauthentic,” — I put it in air quotes because it’s such an overused term — people say things like, “It’s like I don’t know who you are anymore.” Organizations are the same. You come from somewhere.

A just cause is about the future. It’s about where you’re going. It’s about an idealized state of the future that you imagine. You will never, for all practical purposes, get there, but you’ll die trying. Every school district can have a just cause. And that is the striving. The decisions you make are to help you advance a little closer toward that idealized state of the future even though, for practical purposes, you’ll never get there.

The example I often use is Dr. King’s “I Have a Dream” speech. He literally says, “I have a dream.” In his imagination, right? I have a dream that one day little Black children will hold hands on the playground with little white children. He’s talking about an idealized state of the future. He’s talking about it in tangible terms that the rest of us can imagine. We will never actually get to this idealized state. But we, as a nation, will die trying, and all the milestones take us a little closer to the world he imagines, which reinforces that we’re making progress, which inspires us to keep trying.

And schools can do the same. You can have a just cause. You can have a vision of the future. But you have to know where you come from because that’s where your values are established. That’s the dynamic between the two.

DUPRE: During the past year, organizational leadership challenges have been enormous, and superintendents have been profoundly impacted in many ways. We are seeing record numbers of retirements and resignations across the nation, which means many districts will not simply be moving toward recovery following the pandemic, but also transitioning to a new leader. What are some specific actions both the retiring superintendent and the new superintendent can take to minimize the impact of this leadership transition during this critical time?

SINEK: Such a good question! So, the retiring superintendents, whether they forgot or remember, all made a deal — a philosophical deal — to leave this organization in a better shape than they found it. Some made more progress than others, but that’s the deal that they all made. And their last act toward fulfilling that deal must be to prepare their successor for success. They get to set somebody up for success. It’s like kids who do well in life; their parents get some credit. So, when the successor does well, it’s because their predecessor, in some way, shape or form, laid the foundation.

Sticking around long enough to help somebody transition, to share some of the mistakes, to share some of the hidden potholes in the road that they’re going to find, to share some of the unfinished businesses, and to do the job of setting somebody up for success. “These are the things I wish I knew and that I want you to know, that I wish somebody had told me.” That’s deal No. 1.

Deal No. 2 comes from the new superintendents, who cannot let the sacrifices of those who came before them be in vain. Which means it’s not about coming in and changing everything to make their mark; it’s about evolution, it’s about building. It’s about taking everything that worked and amplifying it and re-evaluating everything that’s not working.

I think it’s a fair assessment for every superintendent to ask the question, “Why do we do it this way?” And if somebody can give a legitimate answer, great, then we’ll continue to do it. But, if you can’t say why we’re doing it this way, or if the answer is “This is how we’ve always done it” or “That’s how it’s done,” then those things are on the table. That doesn’t mean they have to be thrown out because sometimes you might discover they work just fine. But I think if you can’t explain, if no one can explain why we do something, then it has to be evaluated. “Because that’s how things are done” is not an answer.

I think what every new superintendent needs to start by doing is by listening, not talking. I think they need to make their way around the organization and talk and have listening sessions with every single person, from the lowest-level employee to the highest-level employee. That’s where I would start. Listening.

DUPRE: Personal wellness is important to you. In The Infinite Game, you wrote, “Leaders are not responsible for the results. Leaders are responsible for the people who are responsible for the results.” In your view, how have school leaders done on that front during the past year? And who takes care of the superintendent?

SINEK: So, it’s a mixed bag, right? The funny thing is you can tell where it was a mixed bag pretty easily. One of the great things that I think came from COVID, a real gift, is that it taught a lot of people in leadership positions empathy.

When COVID happened, we all sort of leaned back in our humanity. And whether someone was an effective or ineffective leader prior to COVID, they did some things that were right because of COVID. In other words, they picked up the phone and they called each of their people and said, “Are you okay?” Or, if somebody had performance issues, instead of immediately thinking that they’re stupid or lazy, which is sometimes what went through our mind in the past, we had a little more empathy and thought, “Well, they’re probably going through something. Maybe a family member has COVID and is sick, or maybe they’re stressed out at home or maybe their kid is driving them nuts.” We started to imagine that there could be other things that are creating what we would consider substandard performance. I hope that practice lasts.

Now, when I said mixed bag, I mean that in some cases, it was easy to tell which teachers were working for a principal or superintendent who was showing empathy because they would have asked the same of their kids. The teachers who simply picked up the phone and told a parent, “Your kid is underperforming” without asking how is she doing — that more likely than not meant no one was asking that teacher if they were OK. It filters down. So if a teacher wasn’t asking about a student, it makes me wonder who wasn’t asking about the teacher. What pressures did they have on them?

The superintendent’s office is a lonely place. I think people forget that everyone in the chain is a human being, and everyone has the same stresses and strains, fears and anxieties, etc. In an organization where there’s a lot of trust, more often than not, someone from the rank and file will look up and ask, “Are you OK?” Leadership is a team sport. Leadership is not a solo affair. Anybody who thinks you can do this thing called leadership alone is in for a horrible surprise.

One of the responsibilities of leaders, when they achieve that position, is to make sure they have people they can turn to in moments of weakness and say, “I can’t do this, I’m scared. I don’t know what to do.” And they have to have somebody who says, “I’ve got your back, even if it goes south, I’ll still be there with you.” You’ve got to have a “leadership buddy” within the system or outside the system. Superintendents can make a deal with other superintendents.

During COVID, I made a deal with some of my friends that all these A-type personalities who were trying to pivot their organizations under extreme stress would call each other all the time. We also all made a deal that there’s no crying alone. That was the deal, no crying alone. So if you’re overwhelmed, you pick up the phone and you cry. Whatever it takes. And just knowing that there’s someone you can turn to when you’re at your weakest or most tired or most frustrated is essential. Not a “nice to have.” Essential.

For someone to choose to express that kind of vulnerability which, let’s be honest, for many is a dirty word, a scary word. It’s not a quid pro quo. You can’t force anybody to do anything. But we can still express ourselves. And we can still express concern and empathy and lend an ear to people who we think need it. At some point, they will feel safe enough to do the same. Asking someone is not an intrusion. You have to be vulnerable. It’s an invitation. “When you’re ready, I’ll be here.”

DUPRE: During the past year, diversity, equity and inclusion has become a prominent issue in most organizations, including schools. I’ve never discussed these issues with you or heard you address them directly. There are many organizations doing important work around DEI, and some that are going through the motions in response to the public outcry. How do we truly bring diversity, equity and inclusion, that important work, to the just cause in a way that it is authentic and part of true organizational development?

Simon Sinek Book Signing
Simon Sinek signs copies of his book, Leaders Eat Last, following an address at a TED Conference in 2014. PHOTO BY BRET HARTMAN

SINEK: To your point, in some cases, unfortunately, it has become checking the box. We did the training. And I think it’s missing the point, which is that it’s not an event; it’s a process. And, when DEI — I even hate the word training — when the DEI process really works, it’s not about highlighting our differences; it’s about highlighting our similarities. When it really works, we’re teaching love.

Chloé Valdary wrote an excellent article about this in The Atlantic. A lot of DEI training backfires because, sometimes, they literally divide the room, one group over here and the other group over there, which is kind of reinforcing the thing we’re trying to not do.

Look, everyone on the planet wants to feel seen, heard and understood, and I think that’s the ambition. It’s a very human desire. And it’s a desperately lacking human skill on how to do that. I think one of the things we forget, and this comes from Valdary’s article, is that whether it’s the African-American experience in the United States or the white experience in the United States, there’s no separating the two. The journey was formed together. The American experience is not this one or that one. It’s this one. You can’t separate them. And I find that very interesting. It’s not what’s my story or your story. It’s our story. How did we find ourselves here today? I find that interesting.

Unfortunately, I think we’re looking for a national solution to a local problem. We’re looking for someone to wave a wand and say, “This will happen,” but, really, these are local problems. It’s how does a school deal with this? How does a school district deal with this? How does a city or a town deal with this, which then adds up to the nation. But I think change starts at home. I think love is the thing we should be teaching, could be teaching.

DUPRE: This has been an insightful conversation, as always. What else do you want to share as we wrap up?

SINEK: I think the challenge that school districts face is very similar to the challenge that a lot of organizations face. People have very strong opinions about how it should work — especially those who have no experience in the profession. If I were to guess, I would say that a lot of teachers don’t feel like their principals care about them as human beings. And a lot of principals don’t feel like their superintendents care about them as human beings.

I would put forward that in the schools that struggle the most, the challenges are actually nothing to do with education, education theory or the kids. It’s leadership challenges. I think that there needs to be much more leadership training given to anyone who wants to have a position of leadership in a school or school district. Things like listening. How do you actively listen? It’s a skill that can be taught. What about how to give and receive feedback? What about how to have a difficult conversation? These skills aren’t taught.

I wish people would stop invoking the children. If I hear another principal say, “My No. 1 priority is the kids….” Newsflash, you’re not a teacher. You don’t interact with kids as often as other people in your school. A principal’s No. 1 responsibility is the teacher. If the teacher feels taken care of, then their No. 1 responsibility will be the child. But if the teacher doesn’t feel taken care of, they’ll spend too much time and energy protecting themselves from other teachers or their own principal or the district or the superintendent. It’s these circles of safety.

So I think there’s a lot of introspection that needs to happen for people in leadership positions simply to say to themselves, “I can do better.”

DUPRE: That’s a great way to finish. Thanks so much for all of your wisdom and for engaging on some of these challenging topics.

Next in Line:

Thought Leadership Series continues in September with an interview of Jon Gordon, author of The Power of Positive Leadership and a dozen other books, by Jill Siler, who has served since 2012 as superintendent of Gunter Independent School District in Gunter, Texas. In September, she joins the Texas Association of School Administrators as associate executive director for professional learning.


Charles Dupre

Retired superintendent

Selected Books by Simon Sinek

Several of Simon Sinek’s books have important applications for school leaders. Here is what I see as the relevancy of three of his published works.

  • The Infinite Game (2019)
    This book sustained me and our organization during the COVID-19 pandemic. It crossed my radar in April 2020, just as the reality of the pandemic was setting in, and immediately shaped the way I led our district’s response. Foremost, our well-established district mission represented what Sinek would consider a just cause. It served as the filter for all decision making as we evaluated solutions for virtual learning, opening or closing schools and drafting health protocols. It would have been easy to throw strategic planning to the wind during such a crisis, but our team found confidence in reimagining our work to fulfill established goals in a different way. We had previously invested time and energy in developing trusting teams and courageous leadership in our organization, so we were prepared to lead through the unplanned and unexpected extreme disruption of our business model and strategic course Sinek calls “existential flexibility.”  The Infinite Game helped us through a year of crisis learning, and Sinek’s principles will continue to guide our work through our post-pandemic response and beyond.

  • Start With Why (2009)
    Sinek’s first book speaks to what some consider to be the most important leadership skill: inspiring those you lead to follow. Sinek drew from the field of mathematics to establish the concept of The Golden Circle, which he uses to show how inspired leaders and organizations operate from a strong “why” at their core. A thoughtful, well-developed “why” supports an organization’s “what” they do and “how” they do it, making up the outer bands of The Golden Circle. As a superintendent, I have relied heavily on principles included in Start With Why to inspire a district culture of excellence that keeps students at the forefront of our work, which is especially helpful and necessary to support effective change management.

  • Leaders Eat Last (2014)
    Strong, positive organizational cultures are developed by leaders who are willing to demonstrate true care and tangible support of the teams they lead — they are willing to place the needs of their team ahead of their own. Sinek is all about developing leaders who inspire others to follow because, even if some people are effective managers, no one rises to the highest level of true leadership without sacrificing their own self-interest. Most educators began as teachers, who are generally hard-wired to put others first. But those who are promoted to leadership opportunities at the campus and beyond may not have received purposeful leadership development to ensure they are able to successfully become a “leader” instead of a “manager.” Leaders Eat Last references established leadership principles and scientific evidence about human biology and behavior to demonstrate that “organizations where people share values and are valued succeed over the long term in both good and bad times.”