Here’s a structured HOSSEC Agenda Template for your next meeting. Full explanation below.
Most professionals answer to a boss. Some prefer to be their own boss. But the strange situation a head of school finds themself in is that they select their own boss, sort of.
The board hires and fires the head, but the actual supervisory support and evaluation takes place through the structure of the Head of School Support and Evaluation Committee (HOSSEC).
If things are going well, the head should have a voice in who joins the committee and how it is structured. Even for experienced heads, this is a black-diamond level leadership challenge.
As a head working with my own HOSSEC, I had meetings go wrong in all sorts of ways. One time I came in hoping to talk through a few real challenges. After my intro speech, what unfolded felt more like an impromptu interview for the job I was already doing. They asked questions I wasn’t ready for. They gave advice I wasn’t asking for. And I left the meeting with a subtle feeling of being more alone than before.
Another time I decided to deliver an impressive presentation on the school’s accomplishments. I spoke for about 30 minutes and turned it over to the committee. They thanked me, said I was doing a great job, and adjourned the meeting 5 minutes later.
I had assumed that good intentions would be enough, that smart and caring people would naturally figure out how to be both supportive and strategic. But without structure and clear framing most meetings were too deferential to be helpful, or too directive to be constructive.
It took me a long time to understand what the committee’s role should be, what kind of support I actually needed, and how to get it. I set out to create a clear, repeatable agenda that could guide our meetings without making them rigid. Something that would make room for honest conversation, offer real support, and build toward shared responsibility and partnership.
We began to open each meeting with a brief welcome and a simple reminder of confidentiality. I trust all the people in the room, but making this explicit signals that this meeting isn’t a performance review, it’s a space for real conversation.
From there, I shared what was most challenging in my work at that juncture. But instead of leaving the committee unsure how to respond, we’ve developed language together: Do I want a sounding board? A reality check? Brainstorming? Strategic perspective? If I told them what I needed, they had a much easier time delivering it. This one shift turned our meetings from “ambiguous check-ins” into targeted, meaningful exchanges.
We also used these meetings to touch base on one or two of my annual goals; not to audit them, but to keep them front and center. We asked: What’s moving forward? What’s stuck? What’s surprising? The questions are formulated from a place of curiosity not interrogation.
Before we closed, we agreed on what (if anything) should be communicated to the Board Chair or the full Board, as well as what follow up steps are needed both from me and from them.
At key points in the year, we shifted focus. We dedicate one full meeting to planning the evaluation process together. We ask: What should we learn this year? What feedback will be most useful? What are the best ways to gather it?
The evaluation process still made me nervous, but the way our conversations were structured over the year made it much more about growth than about gotcha.
My key learning is that structure is kindness. It can generate the clarity, alignment, and shared responsibility that is the foundation of professional trust. And when you’re a head of school trying to do the tough, often lonely work, that kind of trust can be a gamechanger.
Here’s my annotated HOSSEC Meeting Agenda template. Try it out and let me know how it works for you!