The Head of School Archives - Barbara Barron

How to Make Yourself Invaluable to a New Head of School

Barbara Barron — Wed, 19 May 2021 11:10:27 +0000

Revised May 8th 2024 | Originally posted May 19th ’21 by Barbara Barron

It’s the season! “Turn over time.” From Heads of School to teachers and administrative positions, it’s the time of year when we see the postings, the openings, the announcements. People come; people go. It’s a moment in the year that can be as exciting as it is frightening, depending on where you fit in the puzzle.

If your school is undergoing the search for a new Head of School, I’m here for you. This process is far longer and more arduous than pretty much any other, which, frankly, it needs to be! It’s such a critical selection, with wide and deep ramifications. Further, as there are fewer long serving Heads (meaning more than 10 years), a Head search is going to be part of life as we know it now for more schools.

To add current context to this piece, originally posted two years ago, I talked with Sara Shulman who handles development and finance searches at Carney Sandoe. She’s seen Head transitions from the inside and out and brings deep advancement experience to that perspective.

One of the smart points she makes is that having an interim Head of School, especially after a long-standing Head moves on, can be great. It provides a bit of a “bumper”. The Interim can clean up messes, calm nerves, and serve with a sense of neutrality. Further this calming interlude often results in fewer comparisons between the “old” and “new” Heads.

Regardless of the quality of the search process, Sara reminds us that a frequent reason newly appointed Heads (brand new or veteran) don’t stay past the first year is a lack of trust and support from the Board. Ouch!

Further, if a new Head can make it past year 3, they are far more likely to stay until year 7 or 10. If you’ve just gone through a Head transition, you probably aren’t eager to endure another one any time soon! So, let’s be helpful. How? Read on.

I’ve been in this position more than once. I’ve advised several clients about how to make the best use of this key milestone. For our purposes today, let’s focus on how you, the advancement professional, can have a meaningful impact on the transition process and its success. This is because as you help your new Head acclimate and step fully into her or his role as the organization’s chief fundraiser (and make no mistake, she is!), you are also strengthening relationships with your supporters and protecting your program.

With change comes uncertainty. Even if the change that brought the new Head was professionally managed and thoroughly communicated, it’s natural that some in the community might harbor some doubts. Maybe families are worried that the program or the culture will change in ways they don’t want. Conversely: others worry that the program or culture will not change, as they feel it should. Alumni cling to their memories and are fearful that the traditions they cherish might be ignored or forgotten. Teachers are understandably curious (or even apprehensive) about their new boss. (Aren’t you and your team?) Even students, who may be either too young or too self-involved to appear to notice, feel the excitement and anxiety of the adults around them.

And this is all happening when the transition is a healthy one. If not… Well, that’s a whole different article.

So, assuming the good here, how can we as advancement professionals make the most of this opportunity? How can we seize the moment (and it is fleeting) to ensure, as best we can, that everyone steps into their roles successfully?

First things first: it’s essential that you think of yourself as someone who is invaluable to your new Head. Honestly. Who else knows the families the way you do? No one. If we’ve done our jobs well – and we have! – we have the insight, the data, the relationships we can leverage in this moment. Including, and we realize, critically, members of the Board. What you do at the very start of this key partnership will make a huge difference in the years to come. What does that mean? Well, a big piece of that is being crystal clear about priorities from the get-go. This is where you ask for what you need and advocate for your place at the table. Remember, good habits require consistency to take root.

Decide for yourself what are the top five things you need to be successful in your role to ensure your new Head has an excellent first year. Here are some I’ve found helpful:

1. Set a weekly standing meeting with the new Head of School – and keep it. I like one that is early enough in the week to help keep my priorities straight and my energy high. Tuesday morning is my favorite. What’s yours?

This can also be a time that Sara calls a safe space, where your Head can speak freely, with confidence, and you can offer insights she won’t have already gleaned. You’re the one who knows the people well. You know when someone is acting out of character and needs attention. As Sara points out, “The squeaky wheel will always squeak. But when someone normally calm and reasonable is deeply upset, that’s a red flag. We can help our new Heads discern between the two.”

2. Calendar regular planning meetings with other key leaders in advancement and ask that the Head attend. It needn’t be weekly — but certainly every 3 to 4 weeks. The Head needs to learn the value of what you’re doing and then weigh in on important strategic decisions regarding cultivation, stewardship, and messaging.

3. Ask for time reserved on the Head’s calendar to meet with the school’s top donors. You’ll need to customize this for your organization. And you’ll need to balance it with other community-wide opportunities for people to get to know the new Head. But this is likely several hours in each of the early months. Make sure the new Head is prepared for these donor meetings. (Your job is to lean in here!) Create a cheat sheet on each donor family. Once I made a “look book” with photos, and it absolutely helped. No one expects the new Head to know everything. But she or he needs to know some basics about each family and its history with the school. Offer a few good open-ended questions for the Head to ask, like “what drew you to our school?” This meeting provides the Head with the singular opportunity to say thank you while taking zero credit for the family’s past giving.

4. Make sure your new Head gets to meet an array of people, including true cheerleaders and those who embody the school’s culture. Balance the good with the difficult. So much of the job can be usurped by cranky and demanding parents. It’s part of your work to make sure that your Head gets a balanced view of what’s happening with this all-important demographic. Think of this as needing to happen at least once a month.

5. Keep your eyes out for natural fatigue. In addition to everything you want her to learn, there are many others asking her to do the same. If she has an executive assistant, work closely with this key person to build in time for breaks and exercise. The first few months of every school year are jammed-packed with events. Remember, the new Head is taking it all in while trying to remember names, being watched by everyone, and maybe (sadly) not feeling a whole lot of support and trust from her — count them — 20-25 bosses (the Board!)

Perhaps the best piece of advice I got when trying to manage this transition was: never forget that your current Head is still Head until 12:01 am on July 1. Remember who your boss is. That’s the person you need to help shine.

If you could use some help planning for this critical moment in the life of your school, and your career, give me a shout. Shoot me an email. You know I’m always happy to help.

And if you want more advice about building a true partnership with your Head, this article from a few years back touches on those points. I have another article here that discusses ways to support our Head during difficult times.

As always, thanks for all you’re doing.

Good luck and stay well,

Barbara Barron

barbara@barbarabarron.com

How Can You Set Yourself Up So That Next Fall is a Huge Success?April 14, 2026
Metrics That Matter vs. Metrics That Don’tMarch 16, 2026
What is Your Brand?March 2, 2026
Success Story #2February 16, 2026
The Steps We SkipFebruary 1, 2026
What if Fundraising Was Really about Creating Donor Joy?January 21, 2026

The post How to Make Yourself Invaluable to a New Head of School appeared first on Barbara Barron.

Taking Care of Our Heads — of School, That Is

Barbara Barron — Tue, 08 Dec 2020 17:20:49 +0000

by Barbara Barron | Posted December 9th, 2020 | Subscribe to this newsletter

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 balanced by in-person gatherings. Argh!

And I would argue that no one is continuing to feel 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.

Then, remember spring 2020?

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

If it felt like too much, it was. At a conference, the president of CASE actually said these words: “Heads of School were destroyed.” No hyperbole. I personally know of more than one Head who called it quits. Others suffered mightily under the strain and unrelenting pressure. The stakes were nosebleed high for them to get things right. Being Head of School during a pandemic: zero precedent.

My heart went out to them, as I’m sure yours did, 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, refreshed again here.

If you’re like me, you strive to be a trusted advisor to your Head, your donors, and 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 donor meeting, every 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 they hear 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 they need to recover from a challenging meeting. Share the good. But even more importantly, give them 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” when Miranda Priestly blanks on the name of a VIP and Andy (her beleaguered 2^nd 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 4^th quarter, or for us, the spring. 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 it is you do that.

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

Be well.

Barbara Barron

barbara@barbarabarron.com

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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.

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

Barbara Barron — Wed, 11 Apr 2018 05:00:03 +0000

by Barbara Barron | Posted April 11th, 2018

Got a little war story for you.

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 thank them for their generosity but also to discuss their ongoing 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.

“We’re hoping you can consider a gift 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. As soon as I said that gift amount, 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. Felt like we’d asked enough, but 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 terrible feeling in my gut. As an advancement pro, 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 a “no thanks” or a “not now”.

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

Betcha you have some wars stories, too.

When everything is pulled off perfectly, and you and your Head of School step into those special moments 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 heat of the moment!

And conversely, when you march your Head of School into an unmitigated disaster that is a waste of 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… Spiral!

Occasionally, there’s little we can do as advancement pros to change the underlying dynamics of this work. There’s a roller coaster of success and failure is built into the profession, and the sooner we acknowledge that reality, the better off we are.

That said, we CAN 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 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 they hear 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 they need to rebound from a challenging meeting. Share the good. But even more importantly, give them bad news right away. Don’t sit on it, hoping it’ll fade. Get out of your chair and go knock on the door. Best is face to face.

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 and Andy (her beleaguered 2^nd assistant) pulls it out in the nick of time? Be Andy.

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 4^th 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. Overused but true: its 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 advancing its 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 motivate other families who saw them as leaders. They could 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.