Leading With Positivity: A Conversation with Jon Gordon

Type: Article
Topics: Leadership Development, School Administrator Magazine

September 01, 2021

Thought Leadership Series
Jon Gordon1
Jon Gordon, author of The Power of Positive Leadership, says superintendents who remain effective in the midst of adversity have learned to exhibit optimism and encouragement. PHOTO COURTESY OF JON GORDON

In this ninth installment of the School Administrator’s Thought Leadership Series, we feature the thinking of Jon Gordon, author of 23 books, mostly on leadership, notably The Power of Positive Leadership and The Power of a Positive Team

Gordon recently was interviewed by Jill Siler, newly appointed associate executive director for professional learning with the Texas Association of School Administrators and the author of Thrive Through the Five. Siler maintains a leadership blog.

Focusing primarily on The Power of Positive Leadership, Gordon shared his perspectives about what defines a true leader, how to drive the culture of an organization and the importance of investing in the roots of an organization rather than focusing on the fruit. A proponent of meeting challenges with optimism, belief and faith, he encourages superintendents to talk to themselves instead of listening to “the noise of others.”   

The interview has been edited for clarity and length.  

JILL SILER: In your book Power of Positive Leadership, you talk about the difference between “Pollyanna” positivity and an authentic, optimistic, steeped-in-hope kind of positivity that rises up in really difficult times. Can you talk a little bit about the kind of positivity that truly great leaders exhibit?

JON GORDON: I often say it’s not about ignoring reality. It’s about maintaining optimism, belief and faith in order to create a better reality. This is real optimism in a belief of a brighter better future; a belief in your vision, in your purpose and what you’re here to do; and a belief in your people. Leadership is a transfer of belief. As a leader, you believe in what’s possible. You believe in creating this brighter and better future. And, as a result of that, you work to create it, you rally your team toward it.

Now, more than ever, positive leadership is essential. It’s not just a nice way to lead, it’s the way to lead to overcome all the negativity, the adversity, the challenges and the obstacles that every great leader, especially superintendents, faces right now. Probably, one of the most difficult jobs during this past year was a CEO or a superintendent because there was no one answer that made everyone happy. It’s like you were going to upset someone in some way with your decision because there are so many divisive issues and there are so many people who were divided over different things. But this is when you needed this optimism and belief the most. Because if you don’t have it, you can’t share it. 

What we’re talking about here is feeding yourself each day with the real belief, the real optimism that’s rooted in the real stuff that makes a great leader great: trust, belief, optimism, the willingness to work hard and the willingness to do what it takes to move through the adversity and the challenge. It’s having the encouragement to keep going and not giving up when it’s easy to. We don’t give up because it’s hard. We give up because we get discouraged. So you stay encouraged instead of discouraged and, as a result of that, you’re now able to encourage others.

SILER: You quoted Dabo Swinney, the head football coach at Clemson University, who stated: “I’m not an overachiever. I’m an over-believer.” We have seen what you talked about this past year — this difference between a fake positivity versus the leaders who really acknowledge how truly difficult this time is and choose to come together and believe that we’re going to get through this better than we were to start with. 

GORDON: Yeah, you can’t act like it’s no big deal, like “Oh, come on, let’s be positive, let’s move forward.” It’s more like, “Hey, this is hard. This is some difficult stuff that we’re dealing with right now.” We’ve never been through anything like this before, so, if you’re feeling challenged, if you’re not OK, it’s OK to not be OK.

But we can’t allow that to take us down a spiral staircase of despair, of discouragement. We’ve got to lift ourselves up so that we can lift others up. So it’s acknowledging the situation, but knowing that retreating or giving up is not an option. We have to move forward, and we have to believe in what we’re doing, and we have to work to create this future that we want to create and work through the difficulties, work through the challenges. 

SILER: You’ve shared that the leader’s most important job is to drive the culture. You said that “culture is not just one thing, it’s everything. Culture drives expectation and beliefs. Expectations and beliefs drive behaviors. Behaviors drive habits. And habits create the future.” You’ve had this incredible opportunity to interview so many people – CEOs, incredible leaders, the amazing coaches. What does it look like to establish a culture? What does it look like to drive a culture in an organization?

Jill Siler
Jill Siler (left), who spent the past nine years as superintendent in Gunter, Texas, says Jon Gordon’s work speaks to the noise and negativity that can easily confound a superintendent. PHOTO © BY LIFETOUCH NATIONAL SCHOOL STUDIOS

GORDON: When you know what you stand for, every decision you make is easy. You know your core values, you live those values, and you engrain those values in everything that you do. You live and breathe the essence of that culture. It is part of you. It’s part of who you are. It’s part of what you do. Then you engrain it in the people around you, in what you do, what you say, how you think, what you value, what you believe. It’s not static, it’s dynamic. 

But also, culture is something you really can’t quantify but you can feel it. And, so, you’re creating this culture by, again, your essence, by your optimism, your belief, your love, your care, your relationships — all these different factors go into creating the essence of your culture. 

So how do we get all these other people in the organization to actually live and breathe the culture? Because it’s set from the top down, but it comes to life in so many ways from the bottom up. But everyone is contagious creating the culture every day.   

You highlight the successes. You walk into a school building and you see the walls, and what the walls are speaking and saying says a lot about the culture. Then, you walk into another classroom and you see how the teacher teaches and the relationship they have with the students. You see how the students are engaged with people within the organization, the staff and the administrators, and the people who work in the building, in the office, and the support team. All of these different people and all of these different interactions — all of that makes up the culture.

SILER: You shared in The Power of Positive Leadership: “You must create a culture where people don’t just hear your talk, but where they feel your walk. And when they feel the mission and also hear about the mission, then they will be on mission.” That is so powerful. It’s top down, it’s bottom up, it’s all of it together. 

GORDON: Every organization today, every school, has a mission statement. But only the great ones have people who are on a mission. So your job is to create a culture where everyone is on a mission and they’re showing up with that vision and that purpose each day. And they are living and breathing it. 

SILER: You noted that “one of the biggest mistakes leaders make is that they ignore negativity within their team and organization.” You note that in the end it will breed, grow and eventually sabotage the team or organization. This is some of the hardest work we do as leaders. It is easy to identify and address incompetence, but it is somehow much more difficult to address the negativity. What tips would you share with leaders on how to address it?

GORDON: Well, if you’re a superintendent, first and foremost, you have to make sure you’re hiring positive leaders in your schools. Your principals will determine how successful that school is. You put a great principal in a school, that principal is going to do a great job in that school and transform it. If it’s a negative school or a challenging school, they will transform it. It’s always about leadership. So find a great, positive leader who can impact that school. 

We have a Power of Positive Schools program now where we actually take superintendents and principals through a leadership training to be a positive leader. We truly want to transform schools, and the way to do that is through leadership and developing positive leaders. 

Negativity persists and exists. We’ve got to address it, confront it and seek ways to transform it and remove it. Maybe you have to document a negative teacher who is sabotaging the morale and the culture. And, if your mission is to make a difference in students’ lives, you’re not going to let anyone affect that or get in the way of that. 

So, you talk about the cultural level. Then you talk about it at the individual level, through coaching. Coaching those people who need to get on the bus, who may be negative, giving them the tools to transform. If they’re not open, if they’re not willing to change, they’re sabotaging the school, then you have to let those people off the bus. It’s a process of cultural level, team level, individual level, coaching, and then weeding and feeding, feeding the positive, sometimes having to weed the negative. 

SILER: In You Win in the Locker Room First, former Atlanta Falcons head coach Mike Smith shared his story about how at one point he was the second winningest coach in the league when the team was one play and 10 yards short of making the Super Bowl and then went on to win just 10 games in the next two seasons combined. And he shared that the difference was a shift from focusing on the process to focusing on the outcome. Tell us a little more about that story and why the process is so important.

GORDON: Well, in the school system, you so often focus on the fruit of the tree. We focus on our numbers, our test scores. We focus on outcomes. You do have to measure the fruit. But we do so knowing that the fruit is just a byproduct of how well we’re investing in the root. And, if you focus on the fruit and ignore the root — don’t invest in the root, don’t invest in the process — the tree dries up. 

But if you invest in the roots (the people, culture, relationships, etc.), you will see the results. We know that test scores go up when a teacher has a relationship with the student. We know that teacher performance goes up when a principal has a relationship with the teacher. So when we invest in those things, we will get a great supply of fruit. We measure the numbers, knowing they are a byproduct of how well we’re investing in the process along the way.

SILER: One critical element in leadership is the ability to create and share a positive vision. And while plans are important, as you say, “Martin Luther King Jr. said, ‘I have a dream.’ He didn’t say ‘I have a strategic plan that I think might work.’” You talk about the leader as a “dealer in hope” who uses both a telescope and a microscope to lead. Share with us about what it means to lead with vision. 

GORDON: The telescope is your big picture vision of where you want to go. The microscope is the zoom-focused actions you need to take each day to realize the picture in the telescope. You have to lead with both. If you just have the telescope and no microscope, you’re in vision all the time and you’re always talking about the future and you’re excited about it, but you’re not taking the actions necessary to create it. It becomes a delusional process in many ways. If you focus just on the microscope, no telescope, that’s where we’re grinding every day, working hard, pushing ourselves. But what happens? We lose sight of the big picture. We lose sight of the telescope. And we get burned out. We get drained because we lose our vision. And when you lose your vision, you give up, you stop moving forward.

Marathon runners do not give up in the first mile, they don’t give up in the last mile. The last mile is when you’re most physically tired, but you don’t give up then. Why? Because you can see the finish line. Most people quit in the 20th mile. That is where you’re physically tired, mentally drained. You lose your vision.

So when I speak to teachers and educators at those big conferences, I always ask them “What is your 20th mile?” And, if it’s in August, I’ll say, “Please don’t say September.” A lot of times they’ll say March/April, right? And, I always say, “Okay, I want you to write down when your 20th mile is for you, and then write down next to it, ‘Keep my vision alive’ because if you keep that vision alive with the telescope, it will allow you to take actions each day with the microscope.”

SILER: So let’s build on the notion of the marathon. One of my favorite stories in your book is when you talk about Dr. James Gills. He’s a man who’s completed a double triathlon six times. And when you asked him how he did it, he shared this statement: “I’ve learned to talk to myself instead of listen to myself.” And, as leaders, wow is it noisy! This past year has been really noisy with all of the feedback coming at us with COVID and the decisions we’ve been making. What advice would you share with us in terms of how we can talk to ourselves as leaders?

GORDON: Well, that’s the key. You have to talk to yourself because there are so many negative thoughts coming in all the time. And you have to recognize that your negative thoughts are not coming from you.

How do I know? Well, who would ever choose to have a negative thought? Would you ever choose one? Would you ever choose a thought that sabotaged yourself or sabotages your mission or journey? No. You wouldn’t choose those thoughts.

Gandhi said, “I will not let anyone walk through my mind with their dirty feet.” Social media, I will not let anyone walk through my mind with their dirty tweets. We have to stay more positive than the negativity that we face. So as a leader, you’ve got to continually talk to yourself.

Whatever words encourage you, those are the words that you say. For me, I might say before a big talk, “Make a difference. Don’t worry about the audience, just make a difference. Don’t worry about them liking you, just focus on your purpose to encourage and inspire them. It might be “You didn’t come here to be average today. Let’s make a difference.” It might be “My purpose is greater than my challenges.” It might be, spiritually, “I trust in you, God.”

So you’re just constantly talking. When those negative thoughts come in, you replace them with a positive word of encouragement and that allows you to move forward. We have to talk to ourselves more instead of listening to all the negative noise.

SILER: As we’re talking about the noise and the negativity that comes in, one of the things you said that really resonated with me was that “pessimists don’t change the world. Critics write words, but they don’t write the future. Naysayers talk about the problems, but they don’t solve them. Throughout history, we see that it’s the optimists, the believers, the dreamers, the doers and the positive leaders who change the world.” I think that that is such a powerful message, especially for the time that we’re in right now.

GORDON: It’s one of my favorite things to say and remind people of like, “Hey, if you’re a pessimist, you’re not going to change the world.” If we really want to make an impact, we have to remember to stay positive and be an optimist.

Jon Gordon2
Jon Gordon likes to remind his audiences, “If you’re a pessimist, you’re not going to change the world.” PHOTO COURTESY OF JON GORDON

SILER: A unique attribute of your writing is that you use different types of writing to help share your messages, from allegories like The Energy Bus and Soup to fables like The Garden to the short stories you share in all of your books. Story telling has been an effective platform to share your leadership truths. How have you found this to be effective and what advice would you give to leaders about sharing their story of the great work they’re doing in their districts?

GORDON: Story is the best way we convey messages, ideas, culture, traditions. Telling stories reinforces the messages and what matters most in our lives, in our communities, in our schools. The story you tell determines that life that you live. The stories that you tell help people understand what matters and what they need to do going forward. 

A lot of times, when we tell stories, it helps people see themselves in the story and what role they play in the story. We can be a hero or a victim. A victim and hero both get knocked down at times. The victim stays down, but the hero gets back up and arms itself with optimism and belief. As a result of that, we create a brighter and better future. Telling stories of hope and triumph and success allows people to feel that success, to take part in it, to enjoy it, to resonate with it. That’s just the way we’re wired. We’re wired for stories. 

By telling stories, you help people remember what’s important. We don’t remember numbers. We don’t remember figures. We don’t remember strategic plans. We remember mission and story and purpose and where we’re going and why we’re going there. That’s what we remember.

SILER: You have often talked about Alan Mulally, the former CEO at Ford, and emphasized his mantra to “love your people” but “make sure you hold your team accountable to the plan, the process, the principles and the values of the culture.” What are some tangible things we need to think about and do when it comes to love and accountability?

GORDON: These are the greatest tools to lead and to really make a difference. Great leaders hold their teams, their people, accountable. But they love them through the process. You’re going to know that I care about you, that I value you, that I appreciate the work that you’re doing in our school and in our district. But along the way, I may have to challenge you to rise up to meet your potential so that you can help us reach our potential. And if you really love someone, you’re going to hold them accountable. Because if you love them, you will not let them settle for anything but their best. You will help them be their best, and that’s what we need to do. 

We often have to go through discomfort in order to grow. And if you don’t challenge someone, they’re not going to grow. So we get comfortable, we get complacent, and sometimes we need that push from a leader. But we do it in an encouraging, supportive way. If you’re always grinding, always pushing, always holding them accountable but not providing love or support, they’re going to resent you. They’re going to chew you out, and you will burn them out. That’s why it’s the right combination of love and accountability together. 

In our leadership training, we have a continuum, and we ask, “Where are you in the continuum between love and accountability?” And then ask, “What do you need to do more of and how?” We help them make that shift and change to provide more of what they are not doing enough of. 

SILER: I love that. I’m reading the book Radical Candor right now, and it has that quadrant framework where you rate yourself on how you “challenge directly” and “care personally.” I often find myself over in this land of “ruinous empathy," where I’m almost too nice and not challenging directly enough. So that continuum that you shared between love and accountability is a helpful tool for leaders.

One of the coaches that you talk about in that section is Buzz Williams, who is one of my favorites. He talked about this notion that love must come first. But by doing so, you then earn the right to push people past their comfort zone. I think that goes back to what you talked about: We have to challenge our people to meet and exceed their full potential. We’re not loving them if we don’t push them to that place.

GORDON: Yeah, I call it love tough, instead of tough love. Tough love doesn’t work anymore. We grew up with tough love, many of us. That was the way it used to be. And now, it’s love tough. If your team or your kids, students, people, don’t know you love them, then they’re not going to listen to you. They’re not going to trust you. But, if they know you love them, you then earn the right to challenge them and push them. So it’s love tough. They’ve got to feel the love before you can challenge them and push them. You have to develop that connection with them and that trust with them and that relationship with them. I always say this: If people knew that you had their best interests at heart, would they be more open to your feedback? Of course they would. If I knew someone had my best interest at heart, I’d be more open to their feedback. That’s how it works. 

SILER: As we have this interview in April 2021, when we are continuing to battle through the COVID-19 pandemic, I can confidently say this has been one of the toughest years for school leaders to lead. We’ve had to make these massive decisions about when and how to start school, how to balance data from health professionals with desires from their own communities and lead within the various constraints from state and federal leaders. From this massive body of work you’ve been involved in around leadership, what advice would you have for leaders as they lead during this time?

GORDON: It has been the hardest year of our lives. Individually, we’ve all dealt with difficult times and difficult experiences, but we’ve never been through anything like this before, and it has been really challenging.

I would say to these leaders: Look forward; don’t look back. Take the lessons that you learned and move on. Don’t be bitter about the past. Get better. Understand that people were operating at the level of their understanding. Give people the benefit of the doubt. No one is perfect. We all make mistakes. 

Take the lessons. What have we learned from this. How do we grow from this and how do we get better because of this? Tell success stories of the past. How we changed, how we grew, how we innovated. Celebrate the resilience of your staff, the resilience of your students, and then deal with hope. Point people toward that future, the excitement that we have going forward, and bring forth the appreciation of connection, of gathering, of in-person events — that we will never take for granted what we have. 

We have adapted, we innovated, and there are so many great stories and so many things we learned from that. And there are so many ways we got better. So talk about that. That’s what I’m doing. That’s how I’m leading my team. That’s what I’m thinking about. I’m not looking backwards. I can’t go backwards. That’s a recipe for misery and despair. I’m going to look forward to creating a brighter and better future and I want you to, as well. 

SILER: I chose the book The Power of Positive Leadership to focus on in this interview because you have dug so deep into a concept that so many people stay really shallow about. And, at the end of the day, in a year that was so difficult, it was your truth that really helped guide my leadership. 

One of the quotes that means the most to me is that “leadership is a transfer of belief. What you believe is possible and the beliefs you share with your team and organization have a big influence on what you create, build and accomplish.” And that starts with us as leaders, and then it emanates throughout our organizations, and I think that’s why that’s so incredibly powerful.

GORDON: Toxic positivity is getting too much attention right now in the movement of education and, yes, it is real. But if it’s toxic, it’s not positivity. That’s the thing. Positivity is not toxic. So we’re actually giving it the wrong name. It’s really just insincerity, it’s avoidance, it’s a lack of empathy. So it’s really not toxic positivity. 

And, yet, as leaders, we need to be careful that we don’t just encourage people to death. We need to listen, understand, know where people are, hear them out and then lift them up and lead them through it. If you are sick, you cannot help someone who is sick. You have to be well and healthy to help someone who is sick. So if someone is really down, the healthier you are as a leader, the more you can help those who need your encouragement and need that life-giving support the most.

Next in Line:
School Administrator’s Thought Leadership Series continues in October with an interview of Daniel Goleman, author of Emotional Intelligence: Why It Can Matter More Than IQ and other books, by Julie Vitale, superintendent of Oceanside Unified School District in Oceanside, Calif.



Jill Siler

Associate executive director for professional learning

Texas Association of School Administrators

Books by Jon Gordon

Several of Jon Gordon’s books have important applications for school leaders. This is what I have seen during my superintendent tenure as the relevancy in four of his works.

  • The Power of Positive Leadership (2017).
    I had grand intentions from pulling my interview questions from several of my favorite Jon Gordon books, until I reopened this one and almost every page was marked from my previous reading. If you’re looking for a book on culture, vision, team building and leading a system to excellence, this is my recommended go-to book.

  • The Energy Bus (2007).
    The subtitle reads 10 Rules to Fuel Your Life, Work, and Team with Positive Energy, and this book does exactly that. The Energy Bus is an easy, fantastic read that engages readers in a story that will ultimately lead to powerful truths about leadership. As leaders, we often discover morale can be incredibly challenging. This book gets at the core of those issues in a completely disarming way.

  • You Win in the Locker Room First (2015).
    Written with former Atlanta Falcons head coach Mike Smith, this book focuses on the elements most important to building a winning team. Framed with the 7 C’s, the book looks at culture, how to be contagious in your leadership, consistency, communication, connection, commitment and caring.

  • Stick Together: A Simple Lesson to Build a Stronger Team (2021).
    In his latest book, Gordon shares a story about a basketball coach determined to build a stronger team. While a quick and easy read, it digs into the power of belief, connection, hope and teamwork. Whether read by your executive team or a middle school sports team, this book fosters deep conversation about what helps and hurts our team’s performance.