Taking Care of Our Heads — of School, That Is

by Barbara Barron | Posted December 9th, 2020

These are crazy days at our independent schools. It seems like every day there’s a confusing change that forces us to rethink education. There’s more to juggle in our daily work than ever. More headaches! Zoom meetings! Argh!

And I would argue that no one is feeling the brunt of this more than our hardworking Heads of School.

Being a good Head of School is a mash-up of demanding and sometimes disparate requirements: they must be gifted, passionate educators first and foremost. They should be good communicators, who can speak and write to various constituencies. (We like it when they can command an audience.) They need to work well with other educators, collaborating, running interference, and delivering tough news.

Add, work well with anxious parents, well-meaning volunteers, and their Boards (often some of each). Don’t forget, they need to understand how the school’s finances work, and don’t. And be eager, willing, and able to ask supporters for money.

Oh! And be ever ready to represent the school in the community including on a Sunday, in the local grocery store. And serve as the school’s public relations whiz, in a crisis. Sometimes all in the same week.

Fast forward to spring 2020.

Suddenly, they need to be instant experts in public health. And PPE. And distant learning. And creating pods. And, oh my heavens, handwashing protocols!

It’s really too much. I know of more than one Head of School who has called it quits. Others are suffering mightily under the strain and unrelenting pressure. The stakes are nose-bleed high that they get this right. Being Head of School during a pandemic: zero precedence.

My heart goes out, as I bet yours does, too. One of my favorite questions to ask a Head is “What can I do for you?” It is always met with a rush of gratitude. Even if the answer is, “Thanks, but nothing right now.” Try asking it!


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So, since my compassion for these fine leaders is in full force today, I offer some tips I originally published in a different article a thousand years ago, back in 2018.

And because the times call for it, I offer them again. If you’re like me, you strive to be a trusted advisor to your Head, your donors, your colleagues. Here you go!

Seven Ways to Foster a Rewarding and Successful Partnership with Your Head of School

1. Make your Head of School look good.

Always. Be prepared. Do your homework and make sure your Head has all the available info prior to any ask. If the prospects say no, at least it won’t be because you botched the prep.

2. No surprises!

I learned this from my first Head of School. If you get wind of something, make sure s/he hears about it from you.

3. Good news first; bad news immediately.

This may be a corollary to #2. When you get a nice donation or a sweet note from a donor, share it first with your Head. It might be just the thing s/he needs to recover from a challenging meeting. Share the good. But even more importantly, give her/him the bad news right away. Don’t sit on it, hoping it’ll fade. Get out of your chair and go knock on the door (or during COVID, call!).

4. Develop an early warning system.

Make sure you know who is coming to the event. Give your Head a cheat sheet. But then stick close by. Remember the scene in “The Devil Wears Prada” when Miranda Priestly blanks on the name of a VIP’s and Andy (her beleaguered 2nd assistant) pulls it out in the nick of time? Be her. Be Andy.

5. Do the heavy lifting.

Maybe it’s drafting a first pass at an important thank you letter when your Head is pressed for time. Or apologizing early for a mistake made in your department so it never escalates. Or redirecting an ask that’s going off the rails.

Once a former Head of mine got so caught up thanking the donors that he said — and I kid you not — “You’ve been so great, I couldn’t possibly ask for more.” To which, I quipped, “Well, he can’t but I sure will!”. Big laugh. And a second gift. Save.

6. Be the cheerleader.

Especially in the 4th quarter, or for us, the spring. (During COVID, it’s pretty much now.) When everyone is tired, your Head may be feeling discouraged, and you’ve already asked nearly everyone you have. Stay positive. Keep at it. I’ve had some fantastic success in May and June. How about you?

7. Take care of yourself.

Dip into the pools of support you have among your team, your colleagues, your friends, and families. Have a laugh. Or take a walk. Replenish your own source, however you do that.

To the Heads who are reading this, thank you for all you’re doing to keep our schools open, safe, and striving towards their fine and inspirational missions. Take good care of yourselves.

About the Author

Barbara Barron is one of the most respected and highly sought-after independent advancement professionals in the country, having worked with dozens of schools in every corner of the United States. She has raised over $20 million for schools where she served as the Director of Development

Barbara is a New York Times bestselling author, speaker, and presenter who currently advises dozens of schools in various capacities. She is considered a thought leader in the world of advancement, with her writing widely shared by professionals in development offices worldwide.

She can be reached via email at barbara@barbarabarron.com

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