True story. In 1998 as Head of School, I was interviewing candidates for the Middle School Head position. At the time, the Middle School operated like an old junior high school, essentially treating early adolescents as if they were smaller versions of 18-year-old students. The program was stale, and the enrollment weak. After interviewing three finalists, I hired the person with no administrative experience based on a story she told me. As a younger teacher in a public school, Susie McGee was frustrated by the lack of progress students were making in the development of their reading skills. She knew that the straight-jacket methods the school was employing, along with its top-down management, stifled student learning. She read and studied; she became an expert on the most forward-thinking approaches to teaching reading. Shortly after she began to overhaul her methods, she was called into the principal’s office and told to go back to the standard method of teaching reading. Undaunted, unwilling to abandon methods that were proving to be successful, and knowing that the vice-principal would be checking up with surprise visits to her classes, she posted a student at the door (slightly opened) to monitor the hallway. If the V.P. was coming down the hallway, the student alerted the other students in the class to put their desks in rows and revert to “standard operating procedure.”

Today, this great educator and I laugh about the interview. “Why did you ever tell me that story in a formal interview?” I ask. “Why did you hire me after I told you the story?” she asks. After sixteen years she, along with her talented faculty, transformed the Middle School into a dynamic, joyful center of learning. The innovations she brought to this division began to creep into the Upper School. Her impact on the school will be felt for years to come.

In the face of declining enrollment and the understandable concern about financial sustainability, independent schools need more entrepreneurial leaders. For an industry that is clearly on its heels, identifying, cultivating and recruiting entrepreneurs to be heads are the most important steps schools can take to address what is turning into an existential crisis. It’s a daunting task when one considers that schools often attract risk-averse educators and promote cultures that rely on seniority and protocols for decision-making. Entrepreneurs are scary; they embrace change and threaten the status quo.

But there’s so much more to an entrepreneur than just change, and though there is always risk when a school hires an entrepreneur, the slow death that many schools are experiencing now is not much of an alternative. Let’s take a closer look at the true nature of an entrepreneur and its relevance to the leadership crisis in independent schools.

Timothy Butler in his 2017 article, “Hiring an Entrepreneurial Leader” uses data from an extensive study of leaders to identify three critical attributes that define the entrepreneur. First, according to Butler, entrepreneurs have an ability to thrive in uncertainty. Butler makes clear that these leaders don’t enjoy risk, but rather feel more comfortable making decisions when there are significant unknowns and the strategic path is unclear. When I asked Kathy McCartney, President of Smith College why she took the job, her response was that of the classic entrepreneur: “I believe in women’s education; I know there are challenges; along with my team, I’ll figure it out.” Many of the independent schools that are struggling don’t realize that they are in a poker game, that decisions are fraught with risk, and that “no decision” or mindless imitation of other schools is a prescription for “death by a thousand cuts.” Heads paralyzed by the unknown or lacking in imagination will not solve our industry’s problems.

Second, Butler identifies a critical quality of the entrepreneurial spirit- the need to be in the middle of producing something of value. Entrepreneurs are not hands-off leaders; they don’t delegate well; they want to have their finger prints on the creation of value- whatever that might be. Implicit in this leadership trait is a desire to learn- creating something of value requires learning. Inimical to the entrepreneurial spirit are protocols, hierarchy, and a deference to seniority- traits all too often found in independent schools. For entrepreneurs, “best idea wins,” and they want to be part of developing and implementing that idea.

Finally, entrepreneurs know how to persuade people to jump on the bandwagon according to Butler. These kinds of leaders know how to sell their ideas. Their passion for creating something of real value is infectious, not only for their boards but also for those working for them. They are always looking for opportunities to sell and re-sell. This default mode is not phony; nor does it “feel like bluster or hype,” (Butler).

Susie McGee, with her disdain for authority and protocol and her passion for results, helped to transform a middle school. She is the classic entrepreneur: 1) unafraid to move forward in the face of uncertainty, 2) insistent on being in the whirlwind of change but without ego, 3) passionate about the cause and able to sell it to anybody, including her own faculty. Independent school education needs more educators like this leader. Data, albeit critical, is not a substitute for passion; “how to” leadership programs are not a substitute for moving forward in the absence of clarity; and great ideas will never add value to our schools unless they are communicated with conviction… over and over and over. Slow deaths may be imperceptible, but they are still deaths.