Which kind of bold leadership? 



If they want to take bold action to confront inequities in their school systems, superintendents must be willing — and able to afford — to burn some bridges along the way.  


Typically, when school board members set out to hire a new school superintendent, they come up with an extremely ambitious wish list. The job requires a bold and visionary leader, they’ll say, someone who’ll be inclusive, collaborative, respectful, and kind but also willing to tell it like it is, pull no punches, and make the tough calls needed to make sure schools put kids first, rather than caving in to parents, politicians, and special interests who want to keep the status quo.  

Fair enough. It’s a challenging job description, but aspiring superintendents embrace the assignment all the same, knowing that while they could easily fail, they’ll have the opportunity to do some good along the way, improving children’s lives.  

The problem is that while school boards may want the new superintendent to act boldly, the job often comes with build-in incentives not to do so. For one thing, the board members who will vote on the superintendent’s contract extension, a few years on, may not be the same people who did the hiring. Indeed, the extension may be decided by board members who were elected specifically because they oppose the things the superintendent was hired to do. 

Or, for example, consider how pension plans work for most school system leaders. In theory, pensions sweeten the pot for public employees: If you agree to take on this exceptionally challenging job, you’ll get a good salary, excellent benefits, and the promise of continued income after you retire. However, to receive that pension, superintendents must be employed as an administrator within the same state for a specific number of years (usually 10). So while you might have been hired to implement dramatic reforms, the rational decision is to lay low for several years. Dramatic reforms tend to make enemies, enemies tend to get you fired, and getting fired will cost you that pension. (Most superintendents receive some kind of deferred compensation such as a TSA or TDA, and the board pays into the pension system, so when they leave they can roll over those funds. These are certainly valuable benefits, but they don’t equate to a full pension upon retirement.)  

I recently spoke with a superintendent who described precisely this conflict of interests. His career path had been fairly typical — he started out as a teacher and then a building leader in one district, and then he became a central office leader in a neighboring district and a superintendent in yet another. After a good 10-year run as district leader, he left the state for a few years. Then he was asked, and agreed, to come back and lead the district where he had started his career. 

As he described it, he had returned to a school system in turmoil, one with a particularly rancid political environment. Why, I asked, would he take on such a difficult assignment? “Look,” he said, “I’ve worked in this state long enough to be eligible for retirement and a full pension. I’m finally in a position where I can do and say whatever I want.” For most of his career, he had played it solid and safe and was considered successful. Only now, fully vested in his pension plan, did he feel he had the license to do whatever needs to be done, no matter what trouble he stirs up, to improve the school system.  

In the biggest districts, superintendents tend to have a little more freedom to act boldly, without concern for their retirement plans. Consider New York City, for example, where Richard Carranza, the new chancellor, has spoken out forcefully — more so than any of his predecessors — about his plans to reduce school segregation, challenge the unfair admissions processes used in selective schools, and address racial inequities throughout the system. It helps that Carranza comes from the outside, has spent most of his career in other states, and knows that he’s unlikely to keep his current job long enough to receive a New York state pension. And that’s the deal when you work in a high-profile district like that one. He can speak his truth and do what he thinks is right, without worrying whether he’s risking his long-term professional and financial security. Whether he chooses to move to another high-profile school district, take over a foundation, or go into the corporate world, he’ll do well. But imagine if he had to worry about getting another job in some small- or mid-size district in New York state. If that were the case, he might have to think twice about being overly bold and visionary. 

Pick your battles 

When I was a doctoral student at Harvard’s Urban Superintendents Program, we were taught that you have to know which hill you’re willing to die on. We studied and were mentored by many of the wisest school system leaders of the day, some of whom had lost at least one job because they had made decisions that were both politically unpopular and the right thing to do for kids, particularly the most vulnerable. As Rudy Crew, former New York City chancellor and superintendent of the Miami schools, told us, “You know you’re going to get fired at some point, so decide now what’s worth getting fired over.” 

The students in that program included some of the most intelligent and passionate leaders I’ve known, many of whom have gone on to do powerful work in school districts across the country. Some graduated but chose not to go on to be superintendents (or haven’t yet), and some chose to lead smaller, low-profile districts, either because they wanted to return to their home state or because they didn’t want to move their families.  

During our time at Harvard, I don’t think we ever talked about pensions, nor did we discuss the personal toll working as a superintendent can take on you and your family, especially if you move from district to district or state to state. But these things certainly do matter, and they ought to factor into leaders’ thinking about how bold they plan to be, or what stand they’ll take, even if it costs them their job.  

When I became superintendent of Stamford, Conn., I had already split my working years between two other states, so I knew I’d likely never be eligible for a generous pension. I don’t regret that decision, as I’ve had a wonderful career thus far. But it certainly does weigh on me. As an almost-50-year-old father of three, my financial sensibilities are quite different from 15 years ago.  

Before taking the job in Stamford, my wife and I made a deal that we’d keep living in Brooklyn, N.Y., her childhood home. We had two kids in diapers, her mother was close by, and we both knew how much time and energy my job would require, so we thought the best option would be for me to commute to work, an hour or more each way. It was a brutal schedule, but it was the right thing to do to maintain a healthy balance of work and family.  

Plus, I suspected that I wouldn’t be staying in that job for the long haul. When it hired me, the board’s top priority was to put an end to the district’s long-standing practice of tracking students (which meant, in practice, that most of the Black, Latino, and poor children were in low-level classes and White and Asian-American children were in honors). It was a challenge that I embraced, and one the Urban Superintendents Program had prepared me to take on. But I knew I would face stiff resistance from parents who benefited from tracking and didn’t want to see it end. Sooner or later, the job would require me to take a stand worth getting fired over.  

Over six years, we succeeded in detracking the school system, and the fight was just as bitter as I expected. Having made more than a few enemies, and seeing no future in Stamford, I left to become superintendent of Montgomery County, Md. I still wonder, though, if I had built my career in Connecticut, settled there with my family, and wanted to stay in the state, would I still have been willing to do the right thing in Stamford?  

Living in Brooklyn meant that I didn’t have to worry about meeting disgruntled parents in the grocery store or having my wife get accosted by a neighbor demanding that I do a favor for her child (both of which, and much more, happened when I led the Montgomery County system). It wasn’t so risky for me to talk bluntly about wanting to do more for the city’s most vulnerable kids, or to call out influential parents for their white privilege. I wasn’t committed to staying in Connecticut, so I could afford to burn a few bridges.  

When I coach and advise new superintendents, I often tell them they need to decide whether their goal is to be the biblical Moses or the biblical Joshua. I’m not a religious person (and I’m not trying to proselytize), but I find it to be an evocative analogy: Are you prepared to be the sort of leader who guides people out of Egypt and dies on a hill in the desert, or would you rather be the sort who leads people into the promised land?  

Too many of our school systems need a superintendent who’s willing to point out that the existing system is unfair and oppressive, directing the bulk of its resources to the kids who already have the greatest advantages. Hopefully, those superintendents will accomplish some positive changes before, inevitably, they make too many enemies to stick around. Other people are better suited — given their temperament, interests, family obligations, or some other reason — to lead a district where the inequities are not so stark, and where they can get on with the business of improving a system that is decent, if not good enough, already. Each can lead boldly, but you probably can’t be both. So the question is, which kind of superintendent are you best prepared to be?   


Citation: Starr, J.P. (2018). On leadership: Which kind of bold? Phi Delta Kappan, 100 (2), 62-63.


JOSHUA P. STARR (@JoshuaPStarr) is chief executive officer of PDK International, Arlington, Va. 

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