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EdCast

The Untold Truths of the Superintendency

The challenges of being a superintendent, and how to attract, support, and retain leaders
Illustration of a woman helping another woman scale mountain

The superintendent’s role is challenging and always evolving, and too often educators step into this leadership position not fully prepared for what’s ahead. As a position with high turnover and equally high isolation at times, Lindsay Whorton, the Holdsworth Center CEO, says we need to be more upfront about the role if we are to attract and retain leaders.

“What we have to do is be honest but also be encouraging and celebrate what an incredible opportunity it is to be in these roles. Yeah, it's going to be hard and there's going to be these pressures. And it's a really complex, intellectually, emotionally, physically demanding job,” she says. “And it represents an incredible opportunity to facilitate a conversation in your community to help advance your district to do the right thing for kids and to really make a significant difference in the lives of both the students who are in your school system today and in the future.”

The transition to a superintendent role often surprises those coming from senior leadership, as it requires them to assume a broader, more public-facing leadership stance. Many new superintendents feel "discomfort" or even disillusionment when realizing how drastically their responsibilities have expanded, including heightened community visibility and accountability.

“What gets tricky is when that sense of discomfort turns into maybe I'm not capable, maybe I don't have the confidence, maybe this isn't something that I can do,” she says. “And so we think by helping people understand that it is normal to experience what we're calling a shift in professional identity, people can be a little bit less destabilized by that experience and can learn through it and get to the other side of feeling more prepared, more capable, more confident about the role that they have as a superintendent.”

Whorton explains that navigating the superintendency successfully demands strong relational skills, strategic vision, and adaptability. A key component to long-term success, she notes, is the ability to foster strong school board relationships, even as boards may change or challenge the superintendent’s direction. Additionally, Whorton advocates for recognizing the superintendency as a role that requires community leadership and suggests a shift toward viewing superintendents as central civic figures.

In this episode of the Harvard EdCast, Whorton discusses whether the superintendent position has changed and why it’s necessary to reframe the role to inspire a new generation of leaders to step into this role.

Transcript

JILL ANDERSON: I'm Jill Anderson. This is the Harvard EdCast. 

Being a superintendent is arguably one of the most challenging jobs in education. It's also becoming increasingly unsustainable. Lindsay Whorton says we need to redefine the role of superintendents if we are to attract, support, and retain leaders. She's president of the Holdsworth Center, a nonprofit focused on leadership development.

In a recent report, she shares untold truths about the job and the increasing pressures faced by these leaders. Many struggle when transitioning into the role, even when they come from other senior leadership positions. Many assume that they're already doing the bulk of the job, only to discover that it requires a new set of skills and approaches, especially around community leadership and managing board relationships. I asked her how the superintendency has changed in the past 10 years. 
[MUSIC PLAYING]

Portrait of Lindsay Whorton
Lindsay Whorton

LINDSAY WHORTON: People disagree about whether or not it has changed in the past 10 years, and there are certainly some superintendents who have practiced for many, many years who say the details are a little bit different, but it's basically the same job that it was 10 years ago. As we work with new superintendents and as we talk with folks who have experienced the last five to seven years, there may be some truth in saying, yeah, it's the same elements, but I do think there is a shift in the velocity of what's happening. I mean, things just move a lot more quickly. Even with the media landscape that we're in, there's just a lot more opportunities for people in communities to raise issues, raise concerns. The speed at which a small issue might become large or a superintendent needs to engage with or respond to their community feels different to a lot of people. So I do think the shift in the media environment is a big part of the shift that's happening that makes the pressures feel a little bit more intense.

And obviously a lot of people are talking about just how polarized and divided we are as a country and the way that that's showing up in schools and districts, even that is connected to what's going on with our media landscape. So I think those are two big things.

And then on a positive front, I mean, I think we're having important conversations about students that haven't been served well in our system for a long time but are really digging in and having those conversations in a serious way right now. And that's a really good thing but it does mean that there's more pressure on superintendents and on school districts to meet the needs of all kids in their communities.

JILL ANDERSON: How do most superintendents find their way into these roles?

LINDSAY WHORTON: There's a couple of different paths, but, commonly, most people who become a superintendent have worked their way up through the system. So most superintendents have been teachers, most superintendents, by a big percentage, have been principals. And then depending on whether you move into a smaller district or a larger district, you may have spent different amounts of time in central office.

So, for the most part, even by law, by policy in Texas, I think you're required to have been a teacher to be a superintendent unless there's a waiver. So, for the most part, people have worked their way up through the classroom. You're a little bit more likely to become a superintendent if you've been on the academic side of the house versus one of the other pathways.

We really focus on Texas. Three big ways that people move into the role-- one is to move earlier in your career into a smaller school district. So, in Texas, there's 1,200 districts, 900 of them are smaller than 2,000 kids. There might be folks who move even from a principal role or early into central office into those positions.

There are some folks who work their way up within one system in a larger system and then maybe promoted internally. We saw a little bit more of that during COVID as, I think, districts were looking for stability and continuity when there was change.

And then the third is the bouncing around strategy, folks who move to increasingly larger districts, increasingly larger positions until they enter the superintendency. And there's obviously lots of fine grained differences, but, I think, those are the three major pathways that folks take.

JILL ANDERSON: It seems like it's a big shift for a lot of these folks. At least in your report, superintendents seem to experience a disillusionment on the job and it seems like it happens fairly early on. They're just struggling. Is this a case where they get into these positions and realize it's just not what they thought it was going to be?

LINDSAY WHORTON: There are ways in which the shift into the role can be surprising for new superintendents.

JILL ANDERSON: Yeah.

LINDSAY WHORTON: Let's say you're a deputy in a large district and then you move into a superintendent role, either in your community or somewhere else. A very common story that we hear is when you're the deputy, you can come to think I'm basically doing the entire job of the superintendent. There's only a small number of things that I'm not doing at this point. You can underestimate all that is going on in that role that you don't see and how different it really is from the job you did before. That's one of the things that we really want to draw attention to and normalize so that people can prepare for that and be ready and expect it to feel maybe a little bit more uncomfortable than they think that it will.

The second part of that is because it is a substantially different role than the one that you were in before, even if your other role was big and over a lot of parts of the district, I do think it is normal for people to feel a sense of discomfort with what is new in the role.

What gets tricky is when that sense of discomfort turns into maybe I'm not capable, maybe I don't have the confidence, maybe this isn't something that I can do. And so we think by helping people understand that it is normal to experience what we're calling a shift in professional identity, people can be a little bit less destabilized by that experience and can learn through it and get to the other side of feeling more prepared, more capable, more confident about the role that they have as a superintendent.

There are some aspects of the superintendent role, either as it's always been or particularly what it looks like today, that we're worried about embracing that role. We're worried about saying, you know what, the superintendent is significantly a community leadership role. It is not primarily an extension of what you did, maybe, as a principal or as a deputy. It is different. And I do think that for whatever reason-- I think some of this is the history of education. I think some of this is this fear that our strongest educators wouldn't want that role if we described it in that way. Sometimes we shy away from embracing what is really unique and powerful and important about the superintendent role.

JILL ANDERSON: What is unique and powerful about the superintendency?

LINDSAY WHORTON: In the report, we describe these key shifts. The way we describe the key shifts are different than what you see in a lot of professional standards. When you describe everything that a person needs to know and be able to do, which is certainly a long list, the key shifts are intended to say, yeah, you still have to know and you're going to bring those things from your prior role, but there's actually a small number of things that, one, are going to be unique to the value and the contribution that you can make in this position, and, two, are going to be the elements of your role that feel the most different and maybe where you feel the most stretched.

And so when we talk about the shift in skills, and I think this speaks to what is unique and what is different, we talk about the importance of working with the school board. And I think this is one element that as you're a deputy you see to some degree your boss's work with the school board, but you may not be involved in all of the time and investment that's made in those relationships and in helping those individuals and that group to contribute to the leadership of the district. And so that's a new skill and it can come as a surprise.

I think the amount of time that superintendents need to invest, both in being a visible leader to educators in their district but also to building relationships and partnerships with families, with key leaders in the community, with nonprofit organizations, with people who care about the future of the district, I think can be really underestimated.

And to your prior question, this is where there's probably a little bit of a disconnect because there is a bit of a mentality a lot of times about why is the superintendent out doing all of those things. That can be a bit of a hidden dimension of the job.

And then with those roles comes just being a visible person who is the face of an organization and will get both the praise but especially will get the criticism when things don't go well and how you learn to cope with that. The reality is it just feels a little different psychologically when you don't have anybody else to point to who's responsible for the thing that people are focused on. So I think that's really different. And then we talk about just the importance of great communication. 

The other piece is the importance of really getting up on the balcony and being focused on the vision and the strategy of the district-- a small number of things that are important-- and not having the time or it being your job anymore to be the person who's into all of the details of execution. And I think that's a big change, particularly for people who have been so good at that kind of work.

So those are some examples of where we think there are these shifts that folks have to make and where we think the superintendent role is important and uniquely positioned to set up a district to be successful. But an individual who's making that transition has to be willing to let go of some of the things they've done in the past and they've been really excellent at and embrace these new demands on them. They've got to change how they spend their time and they have to be willing to embrace the discomfort that comes with that shift.

JILL ANDERSON: Yeah, I've seen a lot out there about seeing superintendents more as civic leaders, which is incredibly externally facing, out in the public, not an internal type of role. What about the leadership passage? Why are some superintendents able to navigate this better than others? You do see superintendents out there who stay in the role for a really long time. So what are they doing that maybe some of these others aren't?

LINDSAY WHORTON: Well-- and I'm glad you mentioned that. There's this general comment about superintendents don't stay in the role very long. But, really, if you look at the data, it's a lot more complicated than that. Really, you have a group of superintendents who have really long, successful tenures and then you have a set of districts and superintendents that tend to churn a lot more frequently. And when you average those things, you get to the three years.

And so we spend a lot of time highlighting and we have a lot of those tenured, experienced, effective superintendents on our team because what we believe is that there's a skill set that can be learned and that can be taught, that can help superintendents be more successful and have those longer tenures. 
One thing that is always true is those superintendents have developed a really strong skill set of how they work with their boards. And I think there can be this tendency to say, well, maybe those superintendents who last longer, they just have more stable, less contentious school boards, and so that's what describes this.

But as we've studied superintendents with those long tenures who have been really successful in a district, what we found is they've experienced changes in board leadership and changes in board direction. And sometimes folks who have come on the board really dissatisfied with the direction of the district, but they can describe the moves that they make to work with those board members, no matter what perspective they're bringing to the role, to partner with them, to try to advance the mission and the vision of the district. And so that's one example of the skills that can be built.

So, for us, it's really about how do we help people build skills in those six areas. And then the other part of it is how do you help people understand that those are the key skills that they need to be building, three to five years before they get into role? 
And at Holdsworth, we're trying to partner with those aspiring superintendents and partner with their current boss, the superintendent, to say, how do we give these aspiring, high potential superintendents more opportunities to practice the skills that are going to help them be successful when they move into the role?

And there's obviously some things you can't practice in advance and that's where you just got to support people once they're there. That's what we're focused on, helping people understand what's coming, helping them practice, and then being ready when they make that transition into the role to provide them with support and with the mindsets that they're going to need to learn and develop into those great, effective superintendents.

JILL ANDERSON: I mean, is that one of the things, also, that happens once you get into these roles that support just isn't there? Is it just a lonely position to have because you are at the top and, like you mentioned earlier, there's no one else you can really point to?

LINDSAY WHORTON: This is certainly a common point of discussion of just how lonely these jobs are. And I think there's a lot of organizations that are working to try to provide community and connection and support to new superintendents. We're really focused on helping people understand, when they first make that transition, what are the most important two or three things to focus on. There's a long list of things that you want to get done, but how do you get those first moves to be right and to create the conditions to set you up?

And the board comes up a lot around this transition. They've watched every board meeting, they maybe sat in executive session, but they've never had their first one on one with their new bosses before. And so trying to just provide really practical advice for how people navigate some of those first moves is a key part of the support that we can provide folks.

JILL ANDERSON: How can we help superintendents navigate that pressure from all these outside stakeholders, not just the board members but you've got the parents, you've got the community?

LINDSAY WHORTON: The question is who's "we" in terms of how can we support? One thing those of us who work in organizations that provide support and development to superintendents-- one thing we can do is just normalizing that that is going to feel intense and that doesn't mean you're doing it wrong or that you can't succeed in the role, but just to prepare people.

That it feels intense to be responding to the needs and demands of such a large number of people who really care about their kids, and may have different ideas about what the district needs to do to care for and invest in their kids. And so just to prepare people to say that is going to feel intense, and reframing that as a really positive thing that there are so many people in your community that care about the future of the district.

The other thing that we can do more broadly is more of us can actually get involved locally in our communities because there is a tendency for it to be a relatively small percentage of folks in a community who are engaged with the district. And so no matter who we are and what we do, thinking about how we can be more active in both helping the district identify areas where it needs to improve but also expressing support for the great things the district is focused on and trying to do is something that I think all of us can do to ensure that superintendents are getting a more complete picture of the needs and the preferences of folks in their community.

JILL ANDERSON: I guess the odds are more that when they're hearing from people in the community, it is not a positive and more probably critical.

LINDSAY WHORTON: Yeah, we probably are more likely to be mobilized when there's something that we're concerned about and that's important. But we also should be mobilized when there's something that we want to support to make sure that the board and the superintendent has a fuller picture of the perspective of folks in the community.

JILL ANDERSON: Listening to this, I just think back to the bit about being scared because I think who would want this position. Even if I was in a school system, it just sounds so challenging and lonely.

LINDSAY WHORTON: Yeah. There is certainly probably a part of the report that I wrote that plays into that narrative of it can be intimidating. I think what we have to do is be honest but also be encouraging and celebrate what an incredible opportunity it is to be in these roles. Yeah, it's going to be hard and there's going to be these pressures. And it's a really complex, intellectually, emotionally, physically demanding job. And it represents an incredible opportunity to facilitate a conversation in your community to help advance your district to do the right thing for kids and to really make a significant difference in the lives of both the students who are in your school system today and in the future.

We have a program that enrolls teachers on a team with APs and principals. And a lot of them, when they join the program, say, I never really thought of myself as a leader. I thought I was just a teacher. And at the end of the program they frequently say, now I realize that I am a leader and that I'm someone who can influence what happens not just in my classroom but in other classrooms across our building. 
And some of them stay in the classroom to exert that influence. Others say, now I see a path for me to move into a different role to have that influence. And it's a small example, but I think it extends all the way to the superintendency, which is we have a lot of people working in our schools who are mission-driven and have a passion to ensure that all the kids in their school or in their district receive the education that they deserve. And they just need to see the impact that they could have and see themselves as someone who could really make a difference on a broader scale.

And so I think we have to not just lean on the job is so hard and it's so scary and the politics are complicated and there's a lot of pressures, but we also have to lean on you get to set a vision for a district that can change things in a positive way for kids. And I think there's a lot of educators in our system who are ready to step up to do that.

JILL ANDERSON: And you think by being more honest about the role and, like you say, normalizing it might actually draw more people into this work?

LINDSAY WHORTON: Well, I think it can at least, one, help the folks who move into the role be more prepared. And then I think, as we see more and more superintendents succeeding, we move away from the narrative of seeing superintendents who don't last very long and who are just feeling burned out by the role-- I think that is what might encourage more folks who maybe are earlier in their career to be more open-minded about thinking about the superintendent in five or seven or 10 years.

The people it will serve first is the cohort of superintendents who are moving into that role next. And if we can help them succeed in new ways and really thrive, hopefully that can change the tone and change the narrative for the next cohorts that are coming through the system.

JILL ANDERSON: How do you envision the role of superintendents evolving in the next decade?

LINDSAY WHORTON: It's a good question. We always probably expect more of what we're currently seeing, so probably faster. I mean, our society is just moving at an ever greater tempo as we have access to so much more information. So I would expect that theme to continue.

There's, obviously, I think, a really open question right now about how we will solve at the system level-- and I think superintendents will have to play a big role in this-- how we will find a path for the teaching profession to attract and keep really passionate, committed, talented educators? And what the role of technology will be in supplementing and complementing and hopefully making the work of educators simpler, more focused, more effective? That's a big trend. And it seems likely that our schools will look different than they do today and that will have implications for the superintendent.

And then this is probably more of a hope than a prediction. It connects to this idea of superintendent as community leader, just increasingly thinking of our school districts as interconnected and in partnership with other key community institutions and finding more opportunities to build those bridges and connections versus treating our school districts as an isolated entity.

So superintendents finding ways to be in closer partnership with their city councils, if that's relevant, with the faith-based institutions in their community, with nonprofits who serve students and families, with other governmental institutions, and really actively embracing that bridging and partnership is where I would hope the role would go. But we'll see.

JILL ANDERSON: Lindsay Whorton is the president of the Holdsworth Center. I'm Jill Anderson. This is the Harvard EdCast, produced by the Harvard Graduate School of Education. Thanks for listening. 

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