How Can We Cultivate a Strong Relationship With Our Head of School?

Note: this article was originally published with the title, “The Art of Managing Up: War Stories with the Head of School”


Got a little war story for you.

A few years ago, my Head of School and I were at a solicitation breakfast with a very involved couple from our school. We’ll call them Alison and Greg.

The couple’s two children attended our school. This prominent family made leadership Annual Fund gifts each year and a generous six-figure gift early in our capital campaign. They hosted a wonderful cultivation event for us, and Alison was clearly interested in a volunteer leadership opportunity.

In other words, the boxes were ticked with this couple.

We invited them to meet to discuss their support for the school. So, no surprises, no hidden agendas. (Hate those. Don’t do those.)

Oatmeal and coffee on the table, my Head of School began with the important thank you for their previous and ongoing support. As we’d agreed ahead of time, he handed off to me to ask them to consider a second gift to the campaign.

“This one would be in the $500,000 range,” I said.

Picture this: Greg is sitting next to Alison. The Head of School and I are sitting across the table from both of them. Upon hearing this number, Greg nods, then reaches over and zips his wife’s Prada purse closed.

All the air left my Head of School’s body. I literally felt him slump in his chair next to me.

The meaning of that gesture was not lost on any of us. Even if it was a joke, the message it sent wasn’t. We had asked enough, and the donor was closed for business.

(And, of course, it was lost on absolutely no one that it was a $20,000 purse he had ceremoniously zipped shut, thank you very much.)

I felt such a terrible feeling in my gut. As a Development Professional, I’m used to being rejected in every way imaginable. That’s the job. But there’s something about being rejected with the Head of School present that feels entirely different than your random missed opportunity at a luncheon.

With the Head of School there, the stakes feel so, so, so much higher.

They really do feel like war stories, don’t they?

When everything is pulled off perfectly, and you and your Head of School charge into battle feeling prepared and calm as cucumbers — when you walk away with more than you were hoping for, you’ve never felt closer. Your bond has been forged in the flames of battle!

And conversely, when you march your Head of School into an unmitigated disaster that is a waste of both your Head’s precious time, there’s really no worse feeling in the world. Not only do you feel like you’ve left your Head of School down, you feel like you’ve let your school down. Maybe you feel like this isn’t the right job for you, after all. Like anyone could do this job better…

I don’t think there’s much we can do, as Development Professionals, to change the underlying dynamics of the single most important relationship we have. The roller coaster of success and failure is built into the profession, and the sooner we acknowledge that reality, the better off we are.

What we can do, however, is practice stewardship with our Head of School, very much in the same way that we practice stewardship with our donors, our faculty, and our staff. In other words, we can manage up.

I’ve put together a few tips that I believe will help foster that yummy feeling of mutual trust and admiration between you and your Head of School.

Seven Ways to Foster an Amazing Professional 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 propsects 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.

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” (ha! another Prada reference!) 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.

5. Do the heavy lifting.
Maybe it’s drafting a first pass at an important thank you letter when your Head is especially 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 my Head 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 will!”. Big laugh. And a second gift. Save.

6. Be the cheerleader.
Especially in the 4th quarter. For many of us, that means the spring. When everyone is tired, your Head may be feeling discouraged, and you’ve already asked nearly everyone you have. Stay positive. Stay 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.

Want to print those out? I’ve got you covered. You can download it here.

Remember: in the end, this is the long game. A marathon, not a sprint.

Our Heads may not acknowledge this as often as they should (hear that, dear Heads reading this?) but our professional partnership with them is actually essential to their success. Without us working with them, it’s much harder to keep a school on mission. We don’t just keep the laser focused, we also provide a good share of the resources to keep it powered on.

So I’m sure you’re wondering at this point…

“Barbara, what happened with the zipped Prada purse? The story didn’t just end with him zipping it up, did it?”

It didn’t.

Here’s what happened. After Greg made his move, my Head of School and I each took a deep breath. I asked again.

Why? Because they hadn’t said no. I explained where we were in the campaign. We talked about ways they could leverage their gift to help us finish strong. We explored a role Alison could play in our upcoming gala. We found a way forward.

And, in the end, their gift was the centerpiece of our record-breaking event. Alison went on to serve on the Board for years to come.

It easily could have gone another way, friends. But it didn’t because, in part, I had practiced the daily ritual of stewardship with my Head of School, and when the moment came to be tested, we had the trust in one other to persevere.

It’s beautiful work that we do, friends. Thank you for what you’re doing every day.

And just because it’s fun to occasionally take a break, blow off steam, and swap crazy stories, I invite you to do so here. Yours may be just the thing someone else needs to hear today.

My name is Barbara Barron, and I’m writing this blog to share advice on a profession that I adore.

I’ve been working in the field of Independent School Advancement for nearly 20 years. In that time, I’ve had the pleasure of creating and implementing successful Strategic Fundraising Plans for so many incredible schools. I’ve had the privilege of seeing real growth at The Carey School, Marin Primary & Middle School, Woodside Priory, Crystal SpringsSage Ridge and others. (Maybe we’ve met!)

Nothing makes me happier than seeing a struggling school start to thrive. My hope is that you’re here to make a positive change as well. I hope my advice can be a part of that change.

Shoot me an e-mail if you want to swap tips, or share your voice here.

Let’s do this, together.