The Head of School letter is often one of the most carefully written pieces on a classical school’s website—and one of the least read.
Why? Because it’s usually hidden, too long, or written like a donor update instead of a warm, parent-facing welcome.
But done right, the Head’s letter can build immediate trust, cast vision, and make families feel like they’re in the right place. Here’s how to make sure yours actually gets read.
1. Make It Easy to Find
Too many schools bury the letter three clicks deep under an “About” menu. If it matters, give it a top-level spot—or at least feature it prominently on the homepage or Why Classical page.
Better yet, include a short excerpt on your homepage with a “Read the Head’s Letter” link. This signals that your leadership is visible and engaged.
2. Keep It Under 400 Words
Your head of school might have a lot to say. But online, brevity builds readership. Aim for 3–4 short paragraphs that speak to:
- The mission of the school
- Why classical education matters (link to your Trivium explanation)
- The kind of community you’re building
- A clear invitation to learn more
This isn’t the place for updates, board notes, or long-winded bios. It’s a relational on-ramp for parents who are considering your school.
3. Make It Sound Like a Person, Not a Policy Manual
The tone should feel warm, sincere, and conversational—not academic or institutional. It should reflect the voice of someone who knows and loves the students—not just someone who leads meetings.
Use first person when appropriate. Avoid jargon. And if the school has a strong faith component, let that conviction come through naturally and clearly.
4. Connect to the Larger Story
The Head’s letter shouldn’t exist in isolation. Reference the Trivium, your core values, and your “Why Classical?” page to create a cohesive experience for families moving through your site.
If you’re not sure how to write that page, this post will help.
Want a Second Opinion on Your Head’s Letter?
If your Head of School letter feels long, buried, or disconnected, we’ll give it a quick review. We’ll suggest edits that clarify tone, increase readability, and align the message with your enrollment goals.
Request a free letter critique—we’ll send back notes you can use immediately.
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