It hasn’t been long since we, just like Dorothy, left our own versions of Kansas for a strange land (in our cases, Lakeville, CT). The school year has flown by, with coursework piling up on our desks, hang-outs with friends, several of the sweat- filled mosh pits we call dances, and many other activities that have made our experiences here unique. Thanks to the hard work of many community members, Hotchkiss already feels like home.
But sadly, we must soon bid farewell to our beloved Mr. Bradley, who has led the school with great dedication. Although there is no yellow brick road that will guide us to our next head of school, we can ask ourselves: What are we looking for in a head of school?
The school’s motto, Moniti Meliora Sequamur, already speaks volumes about the kind of leader we need. A head of school is not simply a figurehead who steers the ship from afar; they should walk alongside students and faculty, both guiding and being guided to seek better paths. If Hotchkiss is our Emerald City, then our next head of school must embody the qualities of Dorothy’s trio: the Cowardly Lion’s courage, the Scarecrow’s brains, and the Tin Man’s heart.
A head of school must have the courage and determination to act in the face of uncertainty. Being a leader for over 600 students and 150 faculty members is not for the faint of heart. It requires bravery to make difficult decisions and stand firm in the face of adversity.
Like the Lion, our next head of school must be willing to take risks for the better and inspire us to do the same. We need a leader who isn’t afraid to step into the trenches with us—whether it’s to encourage students, advocate for innovative ideas, or tackle difficult issues. A head of school with courage doesn’t just talk about change; they make it happen.
And every great leader needs brains—not just academic intelligence, but wisdom and creativity. Our next head of school must possess the Scarecrow’s ingenuity to solve problems and think critically. Without these skills, no one can fully grasp the complexities of running a school and balancing academic rigor, emotional well-being, and the other interests of community members. A leader with brains knows that education is not only about preparing students for college, but about helping them navigate life with curiosity and purpose—through speeches, programs, and conversations.
Finally, the Tin Man brings the heart—the most essential quality of all. A head of school with a heart cares about the well-being of every student, teacher, and staff member. They are empathetic, approachable, and kind. They understand that a great school is more than just academics and athletics; it must be a place that students can call “home.”
Like the Tin Man, I want our next head of school to cultivate a culture of belonging. To take the time to listen—not just to the loudest voices, but to the quiet ones too. To celebrate our successes and support us through our struggles. To be there to remind us that we are more than our achievements or our mistakes. I want our next head of school to see us each as individuals with unique potential, inspiring us to see the same in ourselves and in each other. A head of school must know the power of encouragement and the importance of making everyone feel valued. Only then can we have a community based on trust, mutual respect, and compassion. After all, there’s no place like home.
