Ten Durable Leadership Insights

Or, a little more about me...

An introduction to the introduction

The basic facts of my career can be found on my LinkedIn profile and I’ll get to my educator origin story at some point, but in short - I started teaching as a graduate student at Emerson College in 1994 and took a leap in the dark taking a midyear dorm parenting job at Walnut Hill School for the Arts in Natick, MA in 1996. I worked my way up to Assistant Head of School over about twenty years and then I have spent the last seven as Head at the Westover School in Middlebury CT.

It’s been a ride and it is head spinning to think about all the change in the world encompassed in that 26 year arc. 

I also want to make clear that I have nothing but love for Westover and Walnut Hill. Any critiques of the field aren’t built on my experience alone but are underscored by conundrums or incongruities I’m watching my peers struggle with as well. Even at larger independent schools, in the scheme of things, we are working at small, intimate, complex organizations created in a different social and cultural context, not built for rapid adaptation to change. And on top of it all, as we emerge from a global catastrophe, our organizations are very highly stressed.

To give you a sense of my philosophy and outlook, I wanted to share what I originally labeled, with tongue in cheek, The Natick Rules.

The Moscow Rules were informal rules known by CIA operatives in the USSR during the Cold War. I saw this list at the International Spy Museum in Washington DC years ago and kept them in a frame in my Walnut Hill office as an irreverent commentary on administration.

https://en.wikipedia.org/wiki/The_Moscow_rules

Note: Irreverent commentary perhaps, but also nuggets of good wisdom for administrators, such as “Do not harass the opposition.”

Note: Another characteristic of my style is to make connections between education and other unusual sources. I look forward to exploring that as I share links and recs to articles, books, podcasts, etc. in the future.

Years ago, I presented at The Association of Boarding Schools with my dear friend, the brilliant educator and leader Tom Kardel, currently Assistant Head at Kimball Union Academy, on “Management Strategies that Work.” For that presentation, I created The Natick Rules. People stood up to take pictures of these slides; I thought I might be onto something.