courage, identity, enrollment, lead, leadership, school, transformation, choose, choice, tenure, success

The Courage to Choose, The Courage to Lead

At the end of his lengthy tenure, a school head significantly reduced attrition, doubled the number of applications, increased enrollment by 55%, completed three successful capital campaigns, and helped his school become a “player” in a very competitive independent school market. Before he arrived, the school was seen as a bottom-feeder in a constellation of old, prestigious and wealthy schools. There was confusion about the school’s identity—a place for students with learning challenges, a place for average-ability students, a safety school for students applying to the more prestigious schools in the area. In an effort to have as broad a reach as possible, the school contorted itself to enroll as many full-pay students as possible, no matter the student profile.

How did this transformation happen? It wasn’t the head’s marketing expertise, his knowledge of program or his fundraising skills, although each of these played a role in the school’s success. The answer was more simple—the courage to ask difficult questions, the courage to execute the difficult solutions, and the courage to take the school in a direction filled with unknowns.

In many cases similar to the one above, heads might nibble at the edges—create a new website, come up with a new tagline, get the message out, add a few engineering classes, and stop being “the best kept secret” in town. Today there is no shortage of advice from marketing experts, but too often the counsel assumes that 1) the school is delivering on its promise and 2) enough families want what the school is offering and are willing to pay for it. These assumptions don’t indicate marketing problems; they suggest fundamental existential challenges that require thoughtful analysis and the willingness to choose a path. And yet schools continue to gravitate to the easy, less painful domain of “marketing.” Their internal mythologies, derived in many cases from past glory days, make it difficult to do the hard self-examination required for real change. Like the proverbial boiling frog, it’s easy to ignore the pattern of decline and the existential challenge it suggests in favor of some quick marketing fix for a problem that often is not the real problem. But markets don’t lie, and no amount of marketing can overcome a product perceived as weak or not worth the cost.

In the above example the head outlined four possible identities for the school and detailed the possible risks associated with each one. Then he asked the board and faculty to vote and choose one identity. His rationale: “I can’t help this school become its best self until we all agree what the school is supposed to be.” The head forced the school to confront its identity challenge by naming it as such and by forcing the key stakeholders to make a choice. Eschewing the easy “marketing” answers, he was willing to take the school into an unknown territory where there were no guarantees and no false comforts that come from solutions that belie the seriousness of the challenge. His courage to force the school to choose—not his expertise in marketing—provided the catalyst for transformation.

Helping a school choose an identity is hard work. There are no painless short-term solutions. The process will test a head’s stamina and her belief that she is doing the right thing. The head of school will have to lead, not the board of trustees (though trustees will be important partners), and that leadership will involve hard choices that will alienate some stakeholders. In the above example, the head endured angry, crying parents who felt that the school was abandoning their children. He faced angry teachers whose contracts were not renewed because caring for students was not enough anymore. Trustees worried that the school was losing its heart. Despite the inevitable headwinds that come with real change, the head pushed forward.

Schools with ambiguous identities are suffering from the proverbial “death by a thousand cuts.” They may be able to survive, but they will never thrive. In these schools the head must find the courage to ask the hard questions and implement the hard decisions. Nibbling is not a viable option; it’s just a distraction that misses the point.

What are the takeaways for new heads whose schools are facing enrollment challenges?

  1. Determine if your enrollment problem is simply a flaw in execution that can easily be corrected or a burning platform that demands hard choices. Execution flaws might include a weak admissions office, poor messaging, or failure to monitor potential attrition in a particular grade. Existential problems, on the other hand, may reflect an ambiguous identity, a failure to be relevant in the market, or a weak value proposition. Under these conditions, although the school may be able to survive, it cannot thrive without big change. Determining the nature and extent of the challenge is central to devising an appropriate strategy. Fixing a problem is fine for flaws in execution. It is impotent when schools are facing identity issues.

  2. If the school has an ambiguous identity, confront the problem head-on. Study the data and the history. Present your findings to the board and establish the choices that are available, detailing the possible consequences (both good and bad) for each one.

  3. Make the board choose. Identity problems can only be addressed successfully if everyone is on the same page. The board has to walk out on the plank with you, realizing that there is risk with each choice. But in order to inspire both the board and the faculty, you must frame the solution as an aspiration, one that touches both the head and the heart. Hard-headed realism allows the leader to identify and communicate the real challenges the school is facing. But in moving the school forward, those challenges must be reframed as an inspiring vision, one that will motivate trustees and faculty to go above and beyond. 

  4. Know that to bring about real change takes courage. You will have to endure hostility from those invested in the status quo. You will have to make difficult personnel decisions (there is no substitute for talent in executing a plan). Trustees will receive complaints. But the path of least resistance is not an option if you want your school to thrive.

  5. Look for early wins and celebrate them in order to give stakeholders some confidence that the school is headed in the right direction. Creating a virtuous cycle begins with engendering confidence in the head’s leadership. The head cannot keep asking trustees and faculty to make investments without any short-term results. Being a change agent requires the head to constantly monitor the key stakeholders, celebrate their good work, and use achievements as a springboard for more positive change.


Transforming schools takes the courage to ask difficult questions and make difficult choices:

1. What is the school?

2. What is it not?

3. Who does it serve?

4. Who does it not serve?

5. What will the market support? 


This courage emanates from a wellspring of deeply held beliefs and a commitment to the mission and vision of the school despite the many unknowns. This is not problem-solving; it’s leadership.