What Every Head of School Should Do Before September

Leadership

What Every Head of School Should Do Before September

The weeks before the school year begins are among the most consequential of a head's year. Here are the things that matter most — and how to approach them with intention.

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Amy P. Vorenberg
••5 min read
Last updated: August 7, 2026
What Every Head of School Should Do Before September
<p class="lead">The weeks before the school year begins are among the most consequential of a head's year. The decisions you make — and the conversations you have — in August shape everything that follows. Here are the things that matter most, and how to approach them with intention.</p> <h2>Get Clear on Your One Priority</h2> <p>Every head enters the fall with a long list of things that need attention. That's not a problem — it's the nature of the role. The problem is treating everything on the list as equally urgent.</p> <p>Before September, identify the one thing that, if it goes well this year, will matter most. Not the five things. Not the three things. The one thing. This doesn't mean ignoring everything else — it means knowing where your deepest attention belongs, so that when the year gets busy (and it will), you don't lose sight of what matters most.</p> <p>Write it down. Tell your board chair. Tell your senior leadership team. The act of naming it — clearly, publicly — changes how you allocate your time and energy.</p> <h2>Have the Conversation with Your Board Chair</h2> <p>If you haven't had a real conversation with your board chair since June, do it now. Not a check-in. Not a review of the board agenda. A real conversation about the year ahead — what you're hoping for, what you're worried about, what you need from the board, and what the board needs from you.</p> <p>The board-head relationship is the most important partnership in the school. It requires investment, and the fall is a critical moment to make that investment. A head who enters September without a clear, honest understanding of where they stand with their board chair is operating without a safety net.</p> <p>If that conversation feels difficult — if there are things you've been avoiding saying — that's a signal, not a reason to postpone. The harder the conversation, the more important it is to have it before the year begins.</p> <blockquote> <p>"A head who enters September without a clear, honest understanding of where they stand with their board chair is operating without a safety net."</p> </blockquote> <h2>Walk the Campus with Fresh Eyes</h2> <p>Before the students and faculty arrive, spend time on campus as if you're seeing it for the first time. Walk the hallways. Sit in a classroom. Stand in the dining hall. Notice what you notice.</p> <p>What does this place communicate about who you are as a school? What would a new family see? What would a prospective student feel? What would a faculty member returning from summer notice?</p> <p>This isn't about finding problems to fix — though you may find some. It's about reconnecting with the physical reality of the school you lead. Heads who spend most of their time in meetings and in their offices can lose touch with the texture of daily school life. The walk is a corrective.</p> <h2>Reconnect with Your Senior Team</h2> <p>Your senior leadership team has been living their own summers. Some have been refreshed; some have been dealing with challenges you may not know about. Before the year begins, spend individual time with each person on your team — not to review their plans, but to check in as a human being.</p> <p>How are they? What are they looking forward to? What are they dreading? What do they need from you this year that they didn't get last year?</p> <p>These conversations take time. They are worth every minute. A senior team that feels seen and supported by their head enters the year differently than one that feels like a set of functional roles to be deployed.</p> <h2>Prepare for the First Faculty Meeting</h2> <p>The first faculty meeting of the year sets a tone that persists for months. It signals what you value, how you lead, and what kind of year this is going to be.</p> <p>Don't fill it with logistics. Don't read from a slide deck. Don't use it to announce everything that's changing. Use it to remind your faculty why they chose this work — and why this school, this year, is worth their full investment.</p> <p>Tell them something true. Tell them something that matters. Give them a reason to walk into their classrooms on the first day of school feeling like they're part of something worth doing.</p> <p>The logistics can go in an email. The first meeting is for the things that can't.</p> <h2>Take Care of Yourself</h2> <p>This one is last on the list, but it may be the most important. The fall is long and demanding. The head who arrives in September already depleted is in trouble by October.</p> <p>Before the year begins, do whatever restores you. Sleep. Exercise. Spend time with people who have nothing to do with your school. Read something that has nothing to do with education. Remind yourself that you are a person, not just a role.</p> <p>The school needs your best self. Your best self requires care. That care is not a luxury — it is a professional responsibility.</p> <hr /> <p><em>If you'd like a thought partner as you prepare for the fall season, <a href="/lp/fall-leadership">Independent Conversations is here</a>. We work with heads of school at exactly this moment — helping you enter the year with clarity, confidence, and a plan.</em></p>

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#head of school#leadership#fall season#planning#strategic planning
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Amy P. Vorenberg

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