Most independent school board meeting agendas include a head's report, a moment for the head to have the floor and report on . . . well, what? I experienced the head's report as the most politically dense recurring moment on my calendar. It is, in many ways, a teaching moment, an opportunity to frame the school's narrative and to teach that story to the board, a chance to help trustees understand some essential aspects of operations so they can be knowledgable ambassadors of the school, a time to preview difficult or complicated challenges and opportunities, and, coursing through it all, a moment for the head to demonstrate their own worth.
Here are some strategies I picked up as a head, as a trustee, and as a consultant who gets to see many heads in action with their boards.
Use the strategic plan and your yearly goals as a broad framework for the report. This guides the conversation to the proper altitude but still leaves room for news. For instance, your description of the fall's community events gains more weight if it's set in the context of your yearly goal to augment those events to celebrate the return to in person activities, post-pandemic. Framing your report with your goals or the strategic plan goals also reminds everyone of the shared understandings you created and works against goal post moving, or mistaking an operational issue of the day for a strategic effort.
Drop in occasional mini-lessons on essential operational work: how you hire and evaluate people and help them grow in their profession, how students are evaluated in the admission process, how teachers evaluate student work, how curriculum is built, how you help kids find their next school, etc. These are "window" conversations, as opposed to doors, and heads should be prepared to describe the leading edge of any of these topics, places where you're driving change. They're also good opportunities to showcase your senior admin team. If the Assistant Head is directly responsible for teacher evaluation, have her do the mini-lesson, an activity that will also be a part of mentoring these leaders in their own leadership growth. These lessons should go on a long repeat cycle and be woven into new trustee orientation to accommodate for trustees cycling on and off the board.
Last, an excellent piece of advice that I learned from Ann Klotz, the long-tenured head of Laurel School in Cleveland: heads who've been in place for 3 or more years should use the head's report, new trustee orientation and other board moments to tell the story of the school under their tenure. This is a corollary to the seven year itch warning that many heads hear. That is, heads in year 7 often discover that there is no one left on their boards who was present when they were hired. Recounting the important moments in your tenure combats the "what have you done for us lately" urgency that can arise in board culture where everything seems pressing.
Without a plan for this moment, heads risk making a breezy account of "stuff that's happened at school since the last board meeting" and miss the opportunity to build their own political capital and deepen the board's understanding of the school.