Just in time for the extended summer holiday weekend, we’re excited to share with you our summer must reads!  

We’re focused on two themes this summer: 1) understanding the rapidly changing macro-context that independent schools face and 2) how schools should prepare themselves to thrive in the face of these uncertain times and re-envision teaching and learning in response to those macro-conditions. 

At GLP, we are always interested what transitions are taking place in the independent school world, particularly as we are continuing our New Heads Leadership Lab program. 

With that slight introduction, I want to report on a recent conversation Greenwich Leadership Partners had with Jim Wickenden, the veteran president of Wickenden Associates and a seasoned expert on the leadership search environment for independent schools. Throughout the independent school world, Jim is held in high regard for the firm’s successful work and his reputation for experience and understanding of the ever-evolving issues of school leadership and governance. I first met Jim as a teacher when he came to The Taft School to scout out early aspirants for leadership. Jim’s commitment to understanding not just his business but also the independent school world was impressive, so after becoming the headmaster at Blair Academy, I made one of my first off campus trips to meet with Jim in Princeton. Going to Wickenden Associates was sort of a pilgrimage both to pay respects and to glean as much as possible about the lay of the land for independent schools in New Jersey. That early venture proved quite valuable, and from that time forward Jim and I have kept in touch.

When do you actually look forward to going to a meeting? One of the biggest complaints we hear from educators is that they are asked to attend too many meetings that waste their time. As facilitators of meetings, we are constantly asking ourselves: what kind of experience do we want people to have; what makes a meeting valuable, productive and enjoyable?

It occurs to me that most meetings in organizations and schools originate from a logical purpose. Most of the time, they are a forum for advancing a work project, disseminating information, discussing an issue or making decisions. So why so many disgruntled meeting goers? I’ll offer three observations for school leaders. 

Pinpointing exactly when being a head of school (HOS) became more complex and challenging may be a foolish pursuit, yet experienced school leaders do talk about that time. What happened? For experienced heads, there seems so much more to do, to know, to consider, to plan and prepare for. Is it any surprise then that a position that once seemed a natural step for an experienced school professional increasingly feels like a step too far? As the variety and relentless demands of the job are ever more apparent (though compensation has certainly risen), the daunting reality of being a head of school seems less an affirmation of a good career than a big personal and professional risk.