Pressing Questions: What Leaders Do You Admire Outside the School Industry?

Summer 2020

I was recently at the ballet with a fellow head of school, and we were discussing the magic it takes to bring a creative vision to life—to compose a symphony, choreograph a ballet, paint a masterpiece.
We then explored art from another angle: How impressive it is when someone is able to adopt another artist’s creative concept and reimagine it in a completely new and unique way. Take George Balanchine, for example. Before the influential choreographer created his version for the New York City Ballet, Tchaikovsky’s The Nutcracker was a financially unsuccessful, obscure ballet that was not well-liked by audiences or critics. Balanchine’s reimagining turned The Nutcracker into one of the most performed, loved, and recognized ballets in modern times.
This got me thinking about how we can bring this passion for reimagination into our field. Who can we look to outside of independent schools for inspiration? Here’s what my fellow head of school colleagues had to say.
“My former mentor, Tim Cybulski, who has worked in public schools his entire career, shaped my development as a leader in critical ways. Tim taught me the importance of purpose and a clearly defined set of core values, how to live by them, and how to use them to shape your leadership. Tim’s kindness and generosity led me from public schooling to independent schools, where I found my passion and am thriving. Leading without ego and from a values perspective can have an incredible impact on someone’s professional journey in any field.” —Jamie Williamson, head of school, The Windward School (NY)
“My son’s youth travel soccer coach, Coach Kaiser, stresses the importance of engagement, being present, focus, knowledge, support of team, fair play, and enthusiastic fun. The cumulative effect of this consistent mentorship for my 10-year-old is subtle yet profound. Strategy talks during games spark research and further study, and my son has guided countless hours of practice in the backyard with his younger brother. As an educator, I aspire to engage, be present, and make a difference every day. I see my son’s coach facilitate this mindset and am profoundly grateful.” —Chad Cianfrani, head of school, Oakwood Friends School (NY)