How to Make Yourself Invaluable to a New Head of School

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

[email protected]

Related posts: