The school district in the upstate New York town where I live and pay taxes—and where I ran unsuccessfully for the local school board a few years ago—is beginning a search for a new superintendent. I’m not on the board, and the voters made clear they preferred it that way. But the changing of the guard has me thinking about what I would do if I were in the board members’ position.
Hiring a superintendent is the single most important decision a school board makes. The chief executive officer of a school district, the supe is responsible for overseeing operations, managing personnel and budgets, implementing board policies, and ensuring the effective administration of schools. He or she shapes not just policy but the daily experience of students and teachers for years to come. And given how frequently superintendents come and go—often before their ideas have time to take root (or get revealed as ineffective)—the real challenge is not simply choosing the right person, but creating the conditions for durable success.
In my recent writing on durable school success, I’ve argued that the rare school systems that improve and remain high-performing share a few common traits: coherence, focus, and the ability to resist the constant pressure of change for change’s sake. Thus, leadership churn is one of the greatest threats to durability. The onus is on school boards to ask not just, “Who should we hire?” but “How do we create conditions for the new superintendent to create or sustain success?”
A good place to start is by asking better questions.
Hire for the job you actually need done
Most superintendent searches begin with a generic profile: visionary leadership, strong communication skills, commitment to equity. A better approach is to begin with the district’s actual problems:
What are the three or four issues that must be solved in the next five years? What would success look like by the end of the new superintendent’s contract? Improving early literacy? Stabilizing staff turnover? Bringing coherence to curriculum and instruction? Superintendents should be hired to solve specific problems, not simply to “lead.”
Ask about execution, not vision
Education rewards charismatic figures who can talk compellingly about change. School districts need people who have actually delivered it. Ask candidates: What initiative did you lead that measurably improved student outcomes? What did you stop doing when it wasn’t working (and how did you know)?
The gap between announcing a reform and implementing it is vast, and the classroom is where ideas—good, bad, and mediocre—go to die. These questions force candidates to move beyond bromides and homilies and into the mechanics of implementation.
Rage against the initiative machine
One of the most common, yet least discussed, features of school systems is initiative churn. Programs appear, disappear, and reappear either rebranded or in slightly different forms. Teachers adapt to one set of expectations only to be told shortly thereafter that the district is moving in a new direction.
Ask candidates: What did you say “no” to in your last district? How do you prevent mission creep or initiative overload? Stability rarely comes from discovering the perfect new program; it comes from protecting the ones that already work.
Test their understanding of teaching
A simple but revealing question: What does a strong lesson look like? Follow-ups might include: What is the hardest part of teaching well today? What professional development have you led, seen, or approved that actually helps teachers improve?
A candidate who cannot answer these questions concretely is unlikely to improve classroom practice in the district.
Focus on the instructional core
Raising student achievement is not one priority among many. It is the work of a school system and defines a quality district. Everything else—operations, facilities, communications, politics—is in service of that goal or a distraction from it.
Superintendents are not just the district’s CEO. They are (or ought to be) the de facto chief academic officer, responsible for setting the instructional direction of the system: establishing priorities, selecting and implementing curriculum, ensuring coherence across schools and grade levels, and aligning resources—time, money, and people—around improving teaching and learning. That level of granularity might sound unnecessary, even naïve. It’s worth keeping in mind that, while our education debates are often framed around large urban districts, they are statistical outliers: The typical district is far smaller—one reason governance and leadership look or should look very different in most of the country. Even in small to medium-sized districts, the superintendent’s role is unavoidably political. But politics is not the purpose of the job. Improving teaching and learning is—and even in the largest systems, instructional savvy is indispensable to getting it done. So boards should press candidates directly:
- What role should a superintendent play in selecting curriculum?
- How do you ensure that adopted materials are actually used well in classrooms?
- How do you balance teacher autonomy with the need for instructional coherence?
- What evidence do you rely on when evaluating instructional practices?
And perhaps most revealing:
- What would you do if you discovered that classroom instruction across your district was inconsistent or ineffective?
In a well-run district, everything points back to the classroom. And the superintendent is ultimately responsible for making sure it does. A candidate who sees curriculum as merely a procurement exercise or instruction as something best delegated to teachers is unlikely to move the needle on student outcomes. He or she understands that, while they do not teach children directly, they shape the conditions under which teaching happens.
In part, that means protecting teachers’ time. Dylan Wiliam often observes that when teachers are asked to identify something that they will stop doing or do less of to create time and space to improve their teaching, they fail miserably, concluding that everything they do contributes to student learning. “The essence of effective leadership is stopping people from doing good things to give them time to do even better things,” he wrote.
Probe governance and temperament
Even capable superintendents fail when the relationship with the school board breaks down. Boards should ask: How do you handle disagreement with a school board? How do you manage political pressure from the community?
The job is inherently public and often contentious. Temperament—calm under pressure, intellectual humility, and a willingness to play the long game—matters more than many boards realize.
Why this job?
Finally, I’d ask “Why do you want to lead this district?”
A serious candidate will demonstrate familiarity with the community and its challenges. As with any job, a weak candidate will offer a generic answer that could apply anywhere.
Hiring a superintendent is the most important decision a school board makes. But it is not a one-time event. It is the beginning of a relationship that will either enable or undermine long-term success.
The lesson of durable success is not that schools need better ideas. It’s that they need the discipline to stick with good ones long enough to matter.
