The Conversation: How the Board Can Best Support the Head of School

Spring 2020

By Rebecca Scherr

When Hadara Stanton Hersh first assumed the board chair role at The Brandeis School of San Francisco (CA) in 2019, she asked Head of School Dan Glass how she and the board could best support him in his role. Glass has always had a hard time answering this question, and this time was no different. Before he gave Hersh a response, he thought he’d pose the question to his peers on the very active California Association of Independent Schools Heads’ listserv. A flood of stories came in. Accounts of chairs standing by their heads through challenging times. The sharing of a lake house and a boat—and acknowledgment of the importance of work-life balance. The unexpected chicken soup left on the desk when they got into school one day. So many of the heads felt supported by their boards. Glass compiled all of the 50 or so responses and shared the list with his board for an open discussion.

In this edited exchange between Glass and Hersh, they explore what kind of support heads are looking for from their boards and how boards can carry through. Glass also found his answer—making the space to discuss different kinds of help in different moments, and even the importance of acknowledging just how hard it is to ask for it. 

DAN GLASS: Why did you ask me that question, “How can the board best support a head of school?”

HADARA STANTON HERSH: Having served as a president of a nonprofit board, I know that the role requires a lot of support of the head of the organization—in this case, the head of school. Yet coming in new, it’s hard to know exactly how to do that in a way that’s meaningful to you. We have a great board, and we have trustees who want to be supportive—and I think it’s helpful to provide direction up front. In this relationship, there’s such a team approach, but the head and the administration serve very different roles than board members who are usually volunteers. It’s helpful to support that relationship.

So, I want to ask you: Why do you think this is such a hard question?

GLASS: So many colleagues, in their responses, included that they never know how to answer this question. The two of us have talked before about how people offer generalized support—“let me know how I can help”—and sometimes directing that helpfulness is more work than the helpfulness might provide.

There is this interesting example in Jewish tradition. My grandmother recently passed away after a long life, and we were sitting shiva (a practice of gathering as a family and a community in a family member’s home). Mourners don’t knock and wait to be let in. You go in. You don’t ask, “Can I do these dishes?” You do the dishes. You don’t ask, “Where would I find a platter for this fruit I brought?” You make the space your own, and you don’t add that burden of managing your helpfulness.

There are certain kinds of relationships in our lives in which we know to be helpful without needing to check in, but in a lot of professional contexts, there’s a lot of checking in. For me that’s what’s really at the root of it—when I get asked that question of “How can I help?” or “What would be most supportive?” my mind goes to that place of “I’m managing as many people as I can right now.” It can be hard to know, in the moment, what to say.

HERSH: Your shiva example is a good one, and it’s an important one to be mindful of even when we’re not in that type of situation.

GLASS: We’re lucky to get to work with governance consultant Lynn Wendell, who guides our new trustees through an orientation process, and while most of our trustees would say that supporting the head of the school is a key part of their work as trustees, we don’t spend time in the orientation process on how to actually do that. Maybe we should bring Lynn back for a 201 version.

There’s also this high-stakes partnership of the head and board chair, which is cyclical. In your case, you had a six-month shadow period that was also tumultuous in the life of this school. You were right in the thick of complex decision-making that was on-the-job training. How do you account for that cyclicality in it?

HERSH: It is challenging to be in this position suddenly—nothing really can prepare you, like on your first day as head of school, I would imagine. I think two-year terms are reasonable—I know you and I disagree on this—but you have the first year of getting up to speed and learning, and then you have the second year of knowing what the year’s cycle looks like. It’s been informative as we set up our process because it’s not just a matter of individual support, but also of working together to further the mission of the school and to support all the people who work here.

GLASS: In the cyclicality of this, I would think three years feels like a nice amount of time—but we can talk about that later.

Each new chair brings a distinct voice and perspective, and certainly expertise, to the work. You’re the first board chair I’ve worked with who went to a Jewish day school, for example, so you have a different kind of relationship to the model that we’re exploring and expanding upon here. You bring real attention to process. 

HERSH: What’s nice about process is that you can be thoughtful about what you’re intending to accomplish and make sure you’re getting there along the way, in a way that works. Our lives are so busy now that we don’t spend as much time reflecting on why we’re doing what we’re doing. Taking that step back and being thoughtful and intentional allows us to accomplish what we’re aiming to.

GLASS: I’ve returned to this John Dewey quote many times in my life: “We do not learn from experience; we learn from reflecting on experience.” It’s such a beautiful structure for thinking about the mutually supportive relationship between a chair and a head, and I think in some ways, it also goes back to the challenge of that “How can I help?” question. 
HERSH: So maybe it’s not the question that people should be asking as they’re walking away from you—“how can I help?”—but rather, this is how I can help, or this is what matters. Ultimately, that’s what we were trying to get at in asking that question. And I think the answers you got back from your colleagues address that.

People want to feel supported, no matter what. They aren’t necessarily saying I need to receive this type of support to feel supported, but rather that reaching out and following up in an individual way makes a difference.

GLASS: Another thing we haven’t touched on yet is how hard it is to ask for help. It’s hard to know precisely what the support is that you need. As heads and board chairs, we’re dealing with a lot of pretty highly accomplished people, and the assumption might be that you don’t necessarily need help.

HERSH: It’s hard to express vulnerability in a professional context. You have a helpful board, and the opportunities to continue to work together in a supportive way and for the best interest of our school and our community is something our kids are learning. There’s no one right answer to the question, and there is no specific road map. 

GLASS: That’s what I appreciate about this list that we’re discussing—these are the ways that people have felt most supported by their boards, and they’re quite distinct from each other. 

The List

In September, Dan Glass, head of school at The Brandeis School of San Francisco  (CA), asked his peers when they felt most supported by their boards. Here’s some of the responses he received.
➔ They have my back when dealing with difficult situations regarding students, parents, or teachers.
➔ They shift meeting schedules to help me maintain a healthy home life.
➔ They trust me to run the school and support the decisions I make.
➔ They serve as a sounding board and resource for problem-solving (when asked!).
➔ They consistently voice in the community their positive regard for my leadership and the direction of the school.
➔ They give me a heads-up on “buzz” just to be sure I’m aware.
➔ They are thorough and thoughtful in their evaluation process.
➔ They encouraged me to leave right after school on a Friday afternoon and get in a mountain bike ride.
➔ They met with me and a parent who had crossed important boundaries (texting my cellphone at all hours of the night).
➔ They surprised me on my birthday with a dinner reservation (and the bill paid for) for my wife and me.
➔ They set up lunch meetings to catch up and see how they can help.
➔ They have highly functional board committees: meetings with agendas, minutes, and clarity about who, what, and when.
➔ They have sincerely followed through onboard self-evaluation processes.
➔ They use my assistant for scheduling.
➔ They invite me to stuff to extend head engagement with our community and don’t take it personally if I can’t attend (they assume I am prioritizing correctly).
➔ They all pitched in and gave my family a very generous gift card to REI (we’re an outdoorsy family) as a holiday gift.
➔ They cover the tab/bill and don’t expect the school to (it’s weird to turn in receipts with a big wine bill on it).
➔ They take the lead on events to celebrate and honor departing trustees (one less thing for school/administrators/head of school to organize).
➔ They truly uphold and stay out of all specific staffing and personnel issues (and we talk about staffing, in general, all the time, which is great).
➔ They abstain from or leave the room when a topic/issue is related to their kid currently enrolled (happened once, but I appreciated the message to all).
➔ They let me know about parent/alumni emails from the community containing a complaint or problem (so that I know) or bcc me on their responses.
➔ They publicly stand by me in the face of complaints from high-profile community members.
➔ They are consistently thoughtful in checking in on how I am doing as a human being, not just as the head of school.
➔ They raise a huge endowment to cover all tuition assistance.
➔ They are supportive and generative about ways to foster the work we do in the area of diversity, equity, inclusion, and social justice.
➔ They give me freedom over my professional development (e.g., conferences and executive coaching).
➔ They follow my lead on strategic planning for the school.
➔ They allow me to work from home when I need a break from my long commute.
➔ They give me a hotel allowance so that I can stay closer to school from time to time.
➔ They are early and generous with their annual fund gifts.
➔ They check in with my family about how they’re doing, not just with me.
➔ They give me a nice and unexpected bonus at the end of the year.
➔ They believe me when I share something with them.
➔ They show general trust in me.
➔ They offer candid but respectful feedback.
➔ They share an understanding that independent schools are a beast, unlike any for-profit business and different than most other not-for-profits.
➔ They have your back in good times and difficult ones.
➔ They establish and nurture a partnership where trust is strong, and communication is solid.
➔ They make you feel taken care of in not just the material way.
➔ My board chair is a true partner—mentor, friend, helper, confidante, doer, and someone who makes me think and laugh.
➔ They praise me and the admin team in a public forum.
➔ The board president comes to staff meetings and thanks everyone for their dedication and hard work and shares nice things about me.
➔ They come to me before my contract is up and say, let’s get a long-term contract in place.
➔ They support my professional growth.
➔ They publicly issue a statement as needed to show that they trust my judgment and stand by my decisions.
➔ They tell parents and faculty to address any concerns with me and don’t take it upon themselves to try to solve operations matters.
➔ They are prepared for board meeting discussions (i.e., reading the materials on the board drive).
➔ They keep confidence (we had one who did not, and we ended up asking her to leave the board).
➔ They allow me to have a significant influence on who joins the board and who is my next chair.
➔ They support me in financial planning.
➔ They offer me customized healthcare.
➔ They create time for a reading/writing mini-sabbatical (e.g., one week away to read, write, think, and more).
➔ They supported my application to Klingenstein Heads’ program (and the two weeks away—really away).

Do you have a conversation to share? 
Have you had a great conversation with a colleague recently that broke down silos or got you thinking about your work in a new way? Have you chatted with someone on (or off) campus that led to an unexpected collaboration? Tell us about it. Do you know of—or are you a part of—a great student–teacher duo? We want to hear about it. Send a brief description to
[email protected], and we’ll follow up.
Rebecca Scherr

Rebecca Scherr is senior editor/writer at NAIS.