Article by Josh Cobb, Graland Country Day School
It was only a parking space. Still, the sign adorning it, “Reserved for the Head of School,” gave it prominence and weight. Since my promotion from head of the middle school at Graland Country Day School to incoming head of school, I hadn’t dared park in that spot, even during the times that Ronni McCaffrey, my mentor and the school’s head at the time, was away. When the day finally came, Ronni moved out of her office, returned her keys and officially retired. Her position and parking space were mine. Was I ready?
In truth, no new head of school can be prepared for every challenge. But I believed (and still believe) that my 15 years at Graland as a teacher, parent and administrator gave me vast institutional knowledge and helped me forge relationships that would be essential for my success. Those relationships could also complicate matters at times, but, on the whole, they deepened my connection to and understanding of the school’s culture, mission and strategic direction.
Interestingly, independent schools rarely look to develop internal candidates as future leaders. Nor is internal succession right for every school, but it was right for Graland. This is due in large part to the former leadership using intention and foresight in developing a plan to prepare me as a future leader, maintain continuity of mission and begin my headship on a foundation of trust.
The Path to Internal Succession
A couple of years ago at the annual NAIS conference, I attended a workshop on headship transitions presented by Pearl Rock Kane of the Klingenstein Center at Columbia University. Of the heads surveyed in her study, many felt daunted by the financial challenges of running a school. Years earlier, when I had been identified as a potential head of school candidate, both Ronni and our director of finance and operations, Juan Botello, recognized this possible shortcoming and looked to broaden my understanding of the financial side of school leadership.
In addition to this mentorship, I learned much about school finance while completing the master’s program at Klingenstein. A “school finance” class (taught by Sarah Daignault, NBOA’s founding executive director) and a related school-year practicum, including a year-long apprenticeship with Juan, helped me gain a thorough knowledge of the school budgeting process and the work of the board’s finance committee.
After I received my master’s degree, Ronni continued my training by involving me in almost every component of “Graland Ascend,” a blended capital and endowment campaign to fund financial aid, professional development, and a new innovation lab and learning commons, the Corkins Center. She also deputized me as the lead instructional member of the design team. I worked with architects and contractors throughout the building process of the Corkins Center, again working with Juan and sitting on the board’s campus and facilities committee.
As I continued to develop my business acumen, I received on-the-job learning in curriculum implementation, disciplinary action, personnel strategies and enrollment management as head of the middle school. Over my tenure as division head, we narrowed our attrition of fifth-grade students from 29 percent to 8 percent by my penultimate year — spots easily filled with quality new students. I worked hand-in-hand with the directors of admission and communications to achieve full capacity in the middle school.
As the final piece of my training, Ronni asked me to work with the chair of Graland’s strategic planning committee to help craft the school’s next strategic plan. This experience helped solidify my knowledge of school governance, another area where first-time heads sometimes lack experience and expertise. Over five years, I participated in four board committees as well as monthly board meetings, developing my understanding of the fiduciary, strategic and generative roles of boards.
My first day as head was in June. I still felt like somewhat of an imposter, but the training I had received helped me feel confident that the gap between division head and head of school would not be too wide. I was ready to take the leap.
