S05E07 - Being a Transformative Leader in the Face of Complex Challenges | Dr. Quintin Shepherd, Pflugerville ISD

In this episode of Build Momentum, we are joined by Dr. Quintin Shepherd. Quintin has 19 years’ experience as a superintendent and currently holds that leadership role at Pflugerville Independent School District in Texas. He has a demonstrated history of improving school districts in both rural and urban areas in multiple states by being committed to transformational and collaborative leadership focused on doing what is best for the children in each district. Quintin is the co-author of the book “The Secret To Transformational Leadership,” together with podcast co-host Sarah Williamson, and his second book, “Transforming Education for Systemic Change and Empowered Communities,” was published in February 2024

Some Questions We Ask:

• Tell us more about your career as a superintendent. (01:20)
• What is most rewarding about being a superintendent? (04:21)
• What are your thoughts regarding the 2022 and 2023 RAND research, and how do you cope with stress in your career? (06:02)
• How has scrutiny of the superintendency changed over the years? (09:32)
• In what ways have you developed a shared vision for your district with your community? (11:57)
• How are your experiences similar to other K-12 school leaders across the nation? (15:09)
• What is the best way to illuminate the humanity of district leaders? (17:27)
• As advocates for K-12 education, how can we truly support superintendents today? (19:14)

In This Episode, You Will Learn:

• About Dr. Quintin Shepherd’s career in education (01:30)
• The joys of being a superintendent (04:27) 
• The changing nature of stress in this job over time, and his strategies for coping with it (06:29)
• Changes in scrutiny of the superintendency with the rise of the internet (09:38)
• Developing a shared vision for the district and being the chief storyteller (12:17)
• His experiences as a superintendent compared to others across the nation (15:17)
• Humanizing superintendents and district leaders (17:48)
• How supporters can all advocate for superintendents (19:41)

Quotes:
“There are only two types of people who work in schools. There are those who teach and those who support teachers. And never forget that [as a principal] you are now the chief supporter of your teachers in your school. ”

“If I'm not my best self, I can't be an effective leader for the people who are counting on me.”

“Leaders are tremendously adept at filling space. We can create it and fill it all day long, but it's a totally different skill set to be able to create the space and then just hold it for others, to be able to fill that space—and do so in a way that's respectful."

“I'm just a big advocate of going to the community first. It requires tremendous vulnerability, tremendous humility. But if you lead that way, the community will actually step up and help you solve the problem.”

Connect with Quintin Shepherd:
Dr. Quintin Shepherd's LinkedIn
Dr. Quintin Shepherd’s Twitter

Stay in touch with Sarah Williamson:
Free Case Study Guide
SWPR GROUP Website
LinkedIn

Stay in touch with Chad Bolser:
LinkedIn

About "The Secret to Transformational Leadership," which Sarah co-authored with Dr. Quintin Shepherd:
Transformational Leadership Secret website
Purchase the print or ebook

Transcript

Sarah Williamson: 0:05

Hello and welcome to Build Momentum for Education, a Podcast where we explore thought leadership in education. I'm Sarah Williamson, the founder of SWPR Group, an agency that supports public relations, communication strategies and thought leadership support for school districts, education companies and nonprofit organizations.

Chad Bolser: 0:23

And I'm Chad Bolser. Chancellor at Ivy Tech Community College in Indiana. This season, we explore a particularly unique perspective in K 12 thought leadership, humanizing the role of the superintendent.

Sarah Williamson: 0:36

Throughout the many conversations we continue to have with superintendents, a clear theme has emerged about the need to bring more humanity into the role of the superintendency. In this special series, we interview current and former superintendents and researchers to pursue the core question, how can we better see superintendents as real people navigating complex challenges to provide the best possible education for K 12 students?

Chad Bolser: 0:58

We dig deeper into how this important work can help build community, invite collaboration and increase widespread engagement.

Sarah Williamson: 1:08

We can't wait to get started, so let's dive in. Well, today we have a repeat guest to Build Momentum. Welcome back. Dr Quinton Shepherd,

Quintin Shepherd: 1:19

Hi there.

Sarah Williamson: 1:20

Well, would you mind starting Quintin by telling us about your career as a superintendent, all of the districts you've worked and your new role? Tell us about it.

Quintin Shepherd: 1:30

Sure. Yeah, this is now 19 years as a superintendent. I started in a small rural district in central Illinois, where you are literally the one man show. You have to do everything, and I wouldn't trade it for the world. I got to be the finance director, Transportation Director, HR director, Curriculum director. You do it all. And the part that's great about that is you learn what it takes to run a school district. The downside is you can't really be great at anything, because you're just constantly spinning plates. And so, you know, there's like, one or two things that you want to be good at as a leader, but you just don't have the time to dedicate to that, or to become great at that. So I did that for about five years. It was in central Illinois. Amboy was the name of the community, and then I was recruited to Skokie, just outside of Chicago. The first suburb you drive into is you head northwest out of the city. And took over a fairly low performing district there, not by anything they had done, but it was just a matter of big change in student population, refugee population moved there, and so they had seen their academic scores and slide for a number of years, and their financial picture had become one of the worst in the state, the eighth lowest performing district in the state, and had the opportunity to lead that district for a number of years, and won the board governance Recognition Award twice in a row, first district to do that in the state of Illinois, and did some amazing things. And you know how it works? You're living your life and doing your thing and having all kinds of fun, and somebody calls you up one day and says, Hey, would you like to lead a high performing school district in the state of Iowa? So from there, I went to Iowa, and just north of Cedar Rapids, Lynn Mar was the name of that community, served as a superintendent there in a very, very high performing school district, and enjoyed the challenge and the opportunity of being in Iowa and again, just settling into my groove when Head Hunter called me up and said, Look, I know how you love school boards and you love rebuilding communities, and sometimes communities that are in struggle and strife. And this was right after Hurricane Harvey had hit the Gulf coast of Texas and decimated Victoria, which is about halfway between Corpus Christi and Houston. And so he flew me down there to meet this school board and check out the community. And it was an instant, instant love affair. I knew this is where it was, maybe the first real time in my career where it was like I just was destined to be there. I knew I was meant to be there. And so moved my family down to Victoria, Texas, and led that district for the last six years, and got through some of the rebuilding that goes along with that, and had some good student achievement success and great financial success in that district. And you know, as a superintendent, you want to continue to serve in a community for as long as you can be effective. And it was starting to come to the realization for me that it was time to spread my wings and begin looking. And no sooner had I made that decision that I was going to start looking, than Pflugerville Texas popped open, which is essentially connected to Austin. We're just northeast of Boston, and so I was hired here to give my fifth start, because every start is a new start. So this is my fifth start as a superintendent, and I was just I've been on the job now for about six months.

Chad Bolser: 4:17

That's quite a resume and quite a journey along the way. So what have you found to be the most rewarding aspect of serving in a school leadership role?

Quintin Shepherd: 4:27

I think the most rewarding aspect of serving in a school leadership role was something that my grandfather said to me when I first told him that I was going to become an elementary principal. And the reason that he's so important to this story is that he had an eighth grade education, worked on a farm, and when he wasn't farming, he worked as a school custodian. So he went and pushed a broom and cleaned a toilet, and then came home and did the chores. And when I got my college degree and became a teacher and eventually became a principal, I showed up at the farm, and he was well retired at this point, not many years left of his life, and told him he was going to be a principal. And he said, Look, I only know a couple of things about working in schools, he said, but I do know this, there are only two types of people who work in schools. There are those who teach and those who support teachers. And never forget that you are now the chief supporter of your teachers in your school. And I thought that was so brilliant, because it put me exactly where I needed to be, that you're not the head teacher as a principal, you are the chief supporter of teachers, and that was my job, and I've taken that role with me everywhere I've gone. And I think that's the greatest reward that a superintendent has when they recognize that it's not that they're standing on the pinnacle of some mountain or the top of some org chart, but that they are the chief supporters of the most important people who work in school districts, which are the teachers themselves.

Sarah Williamson: 5:37

Yeah. So I just realized, Quintin, you've actually been on the show three times. I just want to point that out. You are a longest standing guest on the Build Momentum podcast.

Chad Bolser: 5:47

That is, that's a record, isn't it? Three is a record, right?

Sarah Williamson: 5:50

No, he's the winner. He's the winner.

Quintin Shepherd: 5:51

If this were Saturday Night Live, like, I would win some serious accolades, some straight credit for this, right?

Sarah Williamson: 5:56

I can send you an SM inaudible group sweatshirt. If you'd like, if you like.

Quintin Shepherd: 6:00

Here you go. I love it.

Sarah Williamson: 6:01

So, swag. So, okay, so we've talked about the joy of your role, but now let's talk about the flip side. We've talked with every guest who's been on this series talking about humanizing the role of the superintendent. We've been discussing the 2023 RAND study that found wasn't just 2023 I think it was 2022 as well, that found that superintendents have one of the most stressful jobs in America. I know that might ring true for you. How have you been able to cope with the stress of this role throughout your career?

Quintin Shepherd: 6:29

Well, it's a great question, and an interesting one at that. I would say the first 10 years of my career, although stressful, it wasn't the type of stress that I've experienced the back half of my career, something rather dramatic changed. And I think not just in communities, but I think nationwide, something dramatic changed in that when I started years and years and years ago, the superintendency and the person who sat in the superintendent's chair was widely respected as the education expert, and that there were just certain things that you knew as a superintendent, and generally speaking, the community said, you know, this is within the superintendent's purview, and you know you trust their judgment to some extent. Now, occasionally you'd hear stories where that wasn't the case, but by and large, I think this was the sort of national belief in the superintendency and the role in the superintendency, and you started to see that wane just a little bit pre pandemic, but then the pandemic sort of solidified everybody again, at least for the first few months, like everybody came back together, and it was we can do this, and we will figure this out. And everybody's kind of holding hands, and life was grand. And then it pretty quickly fell apart after that. And it fell apart everywhere, in for different reasons, and that just created a tremendous amount of both pressure and stress. And those are two different things. They respond differently. There's a great story about William Tell shooting the apple off of his son's head. William Tell, was feeling pressure. His son was feeling stress, right? And as a superintendent, we were feeling both pressure and stress, and I truthfully didn't have great coping strategies or mechanisms for stress, but thankfully, I've worked with an executive coach for most of my career. And so I worked with an executive coach about, like, what are the things that superintendents can be doing, or should be doing, or any kind of education leader to help manage. And the big takeaway from that, for any of the listeners who might need to hear this is, you know, there's just this huge difference between self management and self care. And so what she had me do was just draw a line down a blank piece of paper, vertical line down a blank piece of paper, and on the left side wrote self management, and on the right side wrote self care and self management. The left hand column, that's all the stuff that you do when you're trying to solve problems at work. So like, I leave work and their problems are still there. And so for me, I go work out, or I used to go run or cycle or do stuff like that. And when I was out doing that, I was actually actively trying to solve problems at work. And that self management, it's a good thing. That's a healthy thing. Sometimes people engage in self management strategies that are not healthy, drinking, for instance, or recreational drug use, those kind of things. And yes, it does happen, unfortunately. But then on the other side of the page, on the right side of the page, is self care, and those are the things that you should be doing to fill your cup. And when my executive coach took me through this, I could list exactly zero things in self care. It had been so long since I'd done anything in self care, I couldn't come up with anything. I couldn't even think of anything that I wanted to do if I wanted to do self care. So it was a several month process of me rediscovering what self care actually means, and then committing time in my schedule to actually do that self care, because if I'm not my best self, I can't be an effective leader for the people who are counting on me.

Chad Bolser: 9:32

So how do you think the scrutiny of the role of the superintendent has changed over the past few years?

Quintin Shepherd: 9:38

You know, I think the big part of this, and this, I've written about this for the last 10 or 15 years, and so I sound a little bit like a broken record, but I think the biggest thing that happened from the onset of my career to where we are now is that when I started 20 years ago, the internet, yes, it existed, but it wasn't like the thing that it is now. People did not have the ubiquitous access to information that they have now, so they just trusted the superintendent had some expert knowledge and some expertise, and they allowed him to solve problems. What happened was that now people know I can go to Google and I can search anything pandemic response plan, what should we do about curriculum questions that are happening throughout the state of Florida or Texas or anywhere else? And they can search these questions, and then they find really cool things that school districts are doing, and they find other dumb things that school districts are doing, and they judge you accordingly. And so what I realized, and it took me years to figure this out, is that there's actually a very clear line of demarcation, and it breaks down for me along the difference between complicated versus complex. And if it's a complicated problem, there's one right way to do it. It requires some expertise, Bond defeasance schedules for instance, lots of what we do with HR, lots of what we do with legal, lots of what we do with accounting, these are all complicated, right? And so you should expect perfection for me and my staff, right? Because you're not going to go on Google and figure out how to do a bond defeasance schedule like that's just not going to happen. But then there's this whole other world of decisions that are complex, inherently unknowable, and I think that's where the scrutiny, that's where superintendents over and over and over and over and over again, find themselves in hot water is because they take a complex decision that's inherently unknowable, and they say, I'm going to treat it like it's a complicated decision, and I'm going to tell you the right answer. And then what happens is Chad, who hears the superintendent say this, he's like, Oh, I'm going to go on Google and show you what an idiot you are, and then crucify you. And they will every time. And so like, I go around the country and I just scream at superintendents at the top of my lungs, treat complex issues the way that they're meant to be treated, which is, you go to the community first with the question, not with the answer, and you say, here's this thing we're faced up against. How would you help me solve this problem? And so what's an example of complex inherently unknowable? When should we close schools? When should we open schools? When should we run bonds? How much should we run the bonds for? All of these things are complex decisions, and I'm just a big advocate of go to the community first, and it requires tremendous vulnerability, tremendous humility, but if you lead that way, the community will actually step up and help you solve the problem.

Sarah Williamson: 13:31

Well, that was actually what I was going to ask you about is so we know you're passionate about building community, and I was gonna say, what's your strategy for bringing people together to help see your vision, or, even better, to collaboratively build that vision together? How do you do that? I mean, is it through thought exchange? I mean, that's a very complex way to do it. How do you do that?

Quintin Shepherd: 13:50

Thought exchange is a tool, but you know, it's like any good power tool, in the hands of a great craftsman, you can do really good work, and in the hands of somebody who doesn't know what they're doing, it's dangerous, frankly, right? And so I think the strategy is recognizing that people will come together around real problems, not fake problems, but like, legitimate problems that the district is facing, and you lead with, like I said, the question itself, hey, we're facing this thing where some of our schools are at half capacity and enrollment is declining, and this leads to a whole host of questions that we have about transportation schedules, the economy of scale, and so on and so forth. We'd love to convene a smart group of community members who are interested in this conversation to help us come up with a solution. Every single time you've done something like that, people will come together around the table, and it doesn't have to be on a digital platform. You can do it with task forces in person meetings. Do with students. You can do with parents. You know, you just put the question out on the table. And what it requires of a leader, and this is very humbling, but what it requires of a leader is to recognize the difference between creating and holding space versus filling space. Leaders are tremendously adapt at filling space. We can create it and fill it all day long, but it's a totally different skill set to be able to create the space and then just hold it for others, to be able to fill that space and do so in a way that's respectful and all the rest of it that goes along with it. But I think number one, you come to the community with, like, real, legitimate, complex issues that the community knows that they need to face. Second one is tremendous amount of compassion. Compassion is another word that's key to my style of leadership. Passion is to suffer. Compassion is to suffer with. That doesn't mean suffer for means suffer with. So here's how we're suffering as a school district. Finances are struggling, and the economy of scale and so on and so forth. Staffing, how are you suffering? Parents? Well, we're suffering because we don't want to send our kids two and a half miles to go to a school you can't close the school. Awesome. Let's talk about that suffering, and let's see what we can do to mitigate some of the collective suffering that we have. So coming together around suffering is another key part of it. And then I think the other way that you build community. And again, this was a dawn of realization that happened for me, I don't know 5, 6, 7, years ago, is that part of the role of a good leader is to be the chief storyteller. In fact, I have a coffee cup that literally says that my job description is Chief storyteller. My cards, when I hand them out, say superintendent and chief storyteller. And so like, my job to build community is to go out and tell stories, stories about kids, stories about staff, stories about parents, but telling these stories is what brings people together. And then there's stories that get repeated, and out of that becomes a hero culture, and the myths and legends that great organizations thrive on, this all comes out of stories. And so it's just always storytelling.

Chad Bolser: 16:29

I cannot imagine how you got connected with Sarah if you have a title of Chief storyteller that is so weird to me, I don't, I can't. It's amazing, right? Okay, so how representative Do you think your own experiences are compared to school administrators in your local area, state, or maybe across the country?

Quintin Shepherd: 16:51

From what I gather from my colleagues and peers around the country, I think my experiences are fairly representative of what they've experienced as well. I mean, there's been some tremendous highs, the greatest joy you can possibly imagine, you know, the greatest day you just you can't believe that this is a real job. And then there's been other days that have been just a living hell, for lack of a better way to put it. And I think that when I talk to my colleagues around the country, everybody has experienced some version of that for themselves, because at the end of the day, if you think about it, like you know, for you, Chad, the best day of your life is the best day of your life, and it's really no different than the best day of my life. The best is the best, right? It's the best that you know. And the worst day of your life is the worst day of my life. And it actually isn't any worse, like nobody has a worse day. It's just, it's just your worst. And so when I hear superintendents talk about some of their struggles and some of their successes, I'm like, Yeah, I see that, and maybe I've experienced it in a different way. Maybe it's manifested differently for me. I think the thing that I'm super interested in, and I can't quite, I still can't quite wrap my head around it, is when things have gotten so bad for some of my colleagues that they've lost their position, not of their own choice, right? Or worse, yet, it's taken such a tremendous toll on their health that they can no longer serve in the role. And I think again, that's not a failure of them so much as a failure of the system in not preparing education leaders to be able to manage, to be able to cope, and I think it's also sort of endemic of the superintendency itself, which is that is a very lonely and isolating job. Even when you surrounded by colleagues that are superintendents, you recognize that it's not exactly a always a collegial environment, right? Because there's just a certain I don't want to call it a threat, necessarily, but that you recognize that, you know, people are moving on a regular basis. And so there's a political piece to it, and I think that is relatively unhealthy space for superintendents to be in, because the more isolated and alone that you are and feel, the worse it is for mental health, the worse it is for physical health. That's the part that I'm still trying to wrap my head around, is, how do we the we build better support networks for superintendents and education leaders around the country?

Sarah Williamson: 19:00

Yeah, I mean, that's interesting. That's why we wanted to run this podcast series, is we think that there's a benefit to humanizing the role of the superintendent. What do you think when you hear that? And do you think it would help your peers across the country, if their communities saw the leaders of those districts as human beings navigating complex challenges? Tell us about that?

Quintin Shepherd: 19:21

I don't know. It's an interesting question. This is one that's really fascinating to me, because, yeah, very self servingly, of course, of course, I want people to see me as like a real human being who, you know has feelings and actually needs to eat and sleep and do normal human things. But the fact of the matter is, I think that's a really hard challenge, because the average community member doesn't want to see it that way, and maybe won't see it that way. That you are in charge of the community's two most precious assets, our kids and our money, right? And so you better be better than perfect. You know, like a bad day, you better be perfect. And so I think humanizing the superintendency would be amazing, because that, you know, it's a whole compassion thing, and it speaks to me as a human being. But I think humanizing the superintendency is a yeoman's task at a bare minimum, because I think that the average taxpayer, the average parent, I think their response would be, don't really care. Like, I don't really care that this is the like, this person is responsible for these the most important thing in my life, and they better be perfect or better than perfect. And I don't care if they're having troubles at home, or I don't care if they, you know, just lost their parents, or, you know, whatever struggle or strife they're facing with like they still expect perfection. They still expect the best. And so I think it's a noble task to humanize the superintendency, but I think it's probably more daunting than anyone could possibly realize.

Sarah Williamson: 20:43

Well, we're doing our small part here to help that's what we're trying to do/

Chad Bolser: 20:47

Yeah, and I think this connects to that, because I think one of the things that we've really enjoyed about talking to school leaders from across the country is that we as community members, as parents, as people that are invested in the school corporation, we want to be good supporters of you and our leaders. How do you suggest we go about doing a great job supporting the role of the superintendent for our communities?

Quintin Shepherd: 21:14

That's a great question. I think that one of the first things you do is exactly what you two are doing, is to try to humanize the role and recognize that superintendents and all education leaders principal, they're real people, and they do have legitimate issues that they're facing you know, death or debilitating disease or you name it. It's going on for them too, just like it is for everybody. else who's listening or watching this right now, and I think that that goes a long way. I think the other way to support education leaders is just with this sort of tacit belief and understanding that the world is full of complex problems that are inherently unknowable. And I think we could solve this overnight. I mean literally solve this overnight, if we could help people recognize the difference between a mindset of closed and knowing and open and learning, and most people show up to most problems, close minded and knowing, and it's a very human way to be, and it feels really good. It's like a warm, comforting blanket, you know, like, right now you're asking me questions, and I'm the expert, so I get to be closed minded and I know all the answers. And it feels great, but it's not actually the place where I should be as an education leader. And I think it's not actually where people should spend most of their time, most of their days. They should actually spend their time in the space of open and learning, which is to say, what if I'm wrong, or what can I learn from you? Or what if I'm seeing the world in a different way, and there's a better way to see it. And so whenever folks are having interactions with education leaders recognize that you're entering that space close to knowing the only reason you're talking to the superintendent is because you're mad or angry, or you want something changed, or you know the answer and you're going to tell them the answer, right? But when you're in that mindset, you're actually wrong, like 99% of the time, you're wrong. So what you have to do is you have to walk through this door and say, I have this opinion, I have this view, but I wonder if I can see it from their lens. Then if you could get yourself there and the superintendent could keep themselves there, we'd never have these problems, ever.

Chad Bolser: 23:00

I know that just based upon that answer alone, you will have to come back to the podcast for a fourth time. We can discuss open and close mindset as it pertains to educational leadership. I think we could spend a lot of time on that.

Quintin Shepherd: 23:18

Yes. We could.

Chad Bolser: 23:19

Sarah, not that I'm taking any leaps in this, but that's number four for you.

Sarah Williamson: 23:24

Number four coming back, I'm making a note right now. 2025.

Quintin Shepherd: 23:29

There you go.

Sarah Williamson: 23:30

All right. Well, Quintin, where can our listeners find you and learn more about you, connect with you.

Quintin Shepherd: 23:35

I never really figured out how to do this social media thing effectively. About the only place that you can find me is LinkedIn. I do exist on LinkedIn.

Sarah Williamson: 23:42

That's a great place to exist. I tell everyone, that's the best place. I think personally,

Quintin Shepherd: 23:47

I write a fair bit on LinkedIn, and I'm fairly responsive to direct messages there. Otherwise, you can find me, of course, through our district website. Pflugerville ISD. I can be found and contacted there, or you could somehow figure out how to get in contact with Sarah Williamson, and she also is out of inaudible.

Sarah Williamson: 24:04

I do. I have some information there. So, all right. Well, thank you so much. This has been a pleasure to see you again for the third time on the show, and we will have you back soon.

Quintin Shepherd: 24:17

Good to talk to you guys. Thanks. Have a great day.

Sarah Williamson: 24:19

You too. Bye.

Quintin Shepherd: 24:21

Bye Bye.

Chad Bolser: 24:22

Thanks for tuning into the Build Momentum for Education podcast. If you enjoyed listening today, we would love to hear your feedback, and we'd be grateful if you could leave us a review.

Sarah Williamson: 24:33

This helps us to share these powerful stories with even more people. If you liked what you heard, we'd be honored if you could share this episode with someone in your network. We look forward to seeing you next time on Build Momentum for Education.