Nearly every classical school website has a Head of School bio page. Most include a professional headshot, educational credentials, and a paragraph filled with noble phrases like “passionate about discipleship” or “committed to academic excellence.”

There’s nothing wrong with this—but it’s not enough.

In fact, that polished head bio might be doing less work than you think. Because parents don’t just want to know where your head of school studied. They want to know how they think, how they lead, and whether they can be trusted with their children’s formation.

And the most effective way to build that trust isn’t a static biography. It’s a living voice. Enter the monthly letter.

Parents Don’t Follow Credentials—They Follow Voices

We live in a relational age. Credentials still matter, but they’re no longer the primary currency of trust. What moves people now is consistency, clarity, and conviction. Parents want a head of school who feels like a shepherd—not just an administrator.

A monthly letter from the head gives families a window into your school’s heartbeat. It shows that leadership isn’t hidden in an office, but present, engaged, and leading with both head and heart.

Done well, these letters do far more than any bio page ever could. They model thoughtfulness. They reinforce the school’s mission. They keep parents connected to the “why.”

The Bio Page Can’t Do What a Letter Can

A static bio is like reading a résumé. It tells you what someone has done—but not who they are. A monthly letter, on the other hand, reveals:

• Conviction: What issues or ideas the head cares deeply about
• Clarity: How they speak into complexity with wisdom and grace
• Consistency: Whether they show up regularly to guide the school culture
• Personality: Their warmth, humor, or perspective on everyday school life

This kind of communication is a powerful trust-builder—especially for parents who are still new or considering your school. As we explored in our post on communicating your school’s mission, clarity and tone are just as important as content.

What to Include in a Head of School Letter

Great head letters don’t need to be long or complicated. In fact, brevity works better. Aim for 300–500 words—short enough to read on a phone, strong enough to be memorable.

Each letter might include:

• A short reflection on a virtue or theme being emphasized that month
• A peek into a recent classroom moment, assembly, or conversation with students
• A connection between what’s happening at school and what’s happening in the culture
• A reminder of what formation looks like in practice—not just theory

Here’s an example opening:

“Last week, I stepped into a third-grade classroom and watched a student raise his hand during a discussion on courage. He said, ‘Sometimes courage is quiet—it just means doing what’s right when nobody’s watching.’ That’s what we’re forming here—not just knowledge, but character.”

This is the kind of insight that makes a parent nod, screenshot, and forward it to a friend.

Where to Place the Letters on Your Website

If you want this strategy to work, don’t bury the letters deep in your navigation. Feature them.

Some schools have a “From the Head of School” blog feed. Others link to the most recent letter right from the homepage or the parent portal. A strong integration point would be on your parent portal—a space where returning families already go for updates and resources.

You can also include short excerpts on your admissions pages to demonstrate the school’s tone of voice and leadership transparency. This is especially powerful in contrast to schools that only publish generic boilerplate about their leadership team.

When Letters Become Culture-Shaping Tools

The real beauty of this approach is that, over time, it forms a thread. Your monthly letters become a rhythm that anchors parents to the school’s values. They’ll begin to see patterns: that you care about virtue, that you notice small wins, that you’re not afraid to name what matters.

It’s the same strategic principle behind creating a school blog that serves both parents and SEO. Consistency compounds. When you show up regularly, trust deepens—even if people don’t read every single word.

And here’s the hidden win: these letters also give your staff, teachers, and even board members language they can use. They become cultural reference points, grounding everyone in the school’s mission.

How to Make It Sustainable

Worried this will become just another task on the to-do list? Here’s how to keep it doable:

• Set aside one hour per month to write the letter—it doesn’t have to be perfect, just personal.
• Repurpose parts of it into parent emails, blog posts, or social media captions.
• Keep a running list of classroom moments, virtue themes, or parent questions as idea starters.
• If needed, delegate editing or formatting to your communications team.

This isn’t about perfection—it’s about presence. A heartfelt letter, even with a typo, will outperform a flawless bio every time.

Real Relationships Require a Real Voice

In a world where leadership often feels distant, your head of school can be a calming, credible voice. Not through press releases. Not through speeches. But through consistent, candid communication that builds trust one letter at a time.

So if you want to deepen parent engagement, stop obsessing over the headshot and CV. Start writing letters. Start telling stories. Start sounding like a shepherd, not just a strategist.

Next Step: If you’re redesigning your leadership pages or communications strategy, revisit your campaign landing page to ensure it reflects this same voice-forward approach.