This article appeared as "Finding Harmony" in the Winter 2025 issue of Independent School.
What do heads of school wish their board chair knew about the role of a head? I explored this very question this past July when I took part in a panel at Carney Sandoe’s inaugural Green Mountain Institute for heads of school and board chairs.
It’s no secret that the role of head of school has become more complex over the years, especially since the pandemic, racial reckoning, and the Israel-Hamas war. Perhaps it’s not surprising that as it has become more complex, head tenure has started to look different. According to NAIS’s Data and Analysis for School Leadership (DASL), the average headship tenure has declined to eight years with a median of five years for elementary-secondary school heads. One-third of independent schools have had three or more heads in the past decade, according to NAIS data in 2020.
So when I was asked this question, I thought first about my own experience—that when a head-board chair relationship works well, it’s like a beautiful dance, with give and take of trust and mutual respect and admiration. I also wanted to know more about the experience of my fellow heads. So I reached out to 46 of my closest head friends nationally, asking them to share their wisdom with the single open-ended question: What do you wish your board chair knew about the role of head of school?
I received 32 replies, a 70% response rate—44% from men and 56% from women. Of the 32 respondents, 10% were retired heads; 13% had been in the role fewer than five years; and 38% were in their second or third headship. Only 31% said they had excellent relationships with their current board chairs; however, the majority expressed deep appreciation to chairs for serving their schools.
The responses were thoughtful and thorough, and I noticed five major themes: Heads have an increasingly complex job; heads can internalize the stressors of the role, and recognition is helpful; heads need their board chairs to offer honest feedback and support whilst trusting their expertise; board chairs have tremendous opportunities to use their social capital to help the school and board grow; and board chairs must understand their critical role in managing the rest of the board.
A Complex Job
The head is the only person in the institution who touches every part of it. Heads are the CEOs of a business; however, unlike most organizations, schools are highly emotionally charged. Heads are educational experts who are also responsible for legal, personnel, risk management, and more recently, public health decisions—for which many had little to no formal training prior to headship. “If board chairs understood the demands,” wrote one respondent, “they would understand the need to police their board members and protect the head from stray comment, conjecture, and insulting behaviors.”
Schools tend to be more collaborative and process-oriented than other businesses, which considerably slows down decision-making as heads must also consider multiple perspectives with conflicting needs and priorities. Heads need their boards to understand that. Whilst boards are focused on metrics—and rightfully so—heads are the culture-bearers of their schools, and those in my survey requested recognition for the time they spend building a positive school culture. “It’s not by accident when a school culture is vibrant and joyful—the head of school has built that from the top down,” shared one respondent.
Emotional Support
Heads asked chairs to see them as both holders of an office and humans requiring emotional support. The complexity of the position is such that most heads struggle to truly separate from their schools. This reality was summarized well in one response: “I cannot stop thinking about the school 24/7/365. I try and try, but I do not know how to not think about the future of the school and how I can be of best service to it—sometimes it is exciting, and sometimes it is daunting.” Some requested that their chairs give them explicit permission, without judgment, to not be so consumed with the school. Heads highly value the emotional support that chairs give.
Caring for the head included not contacting the person on weekends for something that could wait until Monday morning; seeking ways to share or lighten the head’s burden; learning about the head’s personal interests; and refraining from asking the head to do the board’s work, such as setting up their meetings and writing their reports. Heads yearn for empathy in managing situations that may not have a solution and can only be managed. “I’m not going to complain and broadcast my vulnerability when I’m having a hard time,” shared one respondent. “You have to ask occasionally and make it safe for me to share.”
Professional Support and Partnership
The well-known phrase “uneasy lies the head that wears the crown” is felt acutely by heads. Many indicated that they were not sure that their board chairs understood how lonely they felt in the position. They welcome ongoing and meaningful feedback on their performance; however, some said that they needed to prod and lead the process, or it would not happen. One head wrote that in an authentic partnership, “Board chairs should be able to voice uncomfortable concerns and still make it clear they have our best interest at heart.”
The heads who responded to my survey also asked that chairs refrain from giving advice until asked. The chair’s role is to provide thought leadership and be a sounding board. In addition, chairs need their own professional development related to governance and nonprofit board leadership, which models ongoing learning for the rest of the board. When the partnership is working well, wrote one respondent, “The head and chair sustain a relationship in which each recognizes that their respective experiences—professional and personal—can be of value to the relationship they form in service to the school.”
Heads also said that unequivocal, public endorsement from the chair and the entire board was vital. True support from the chair, according to one head, means “assuming my competence and expertise and sharing [that] with anyone she interacts with … and less about listening to concerns, complaints, and questions [from others] that would be better directed to me … directly!”
Social Capital
Heads observed that trustees often have a lot of social capital to put toward fundraising and recruiting prospective trustees. Chairs should be one of the first trustees to give to the school. “When they do not contribute financially to the school,” one head explained, “I cannot take them seriously when they say they are following up with other board members regarding their giving.”
Whilst heads want their chairs and trustees to use their networks to fundraise and recruit, trustees must also respect the head’s opinion on board selections, especially if it is a current parent. “I know more about the family and their child’s experience at our school than you do,” wrote one head. Trustees must also maintain strict confidentiality if a head vetoes a trustee candidate.
Board Management
Many of the heads said they wished their chairs understood that the chair’s job is to help board members act as a body rather than a group of individuals. One said it was helpful for board culture if multiple former board chairs remained on the board. Former chairs can help other trustees understand the work it takes to corral board members, leading to a more cooperative and higher functioning board.
Heads also need their chairs to redirect board meetings if they go off-course. “At a meeting when a trustee asks me a question that veers into operations and sends us down a rabbit hole, it’s really hard for me to stop it because this trustee is also my boss,” wrote one head. “It’s up to [the chair] to redirect and do some board education in real time.” Likewise, chairs need to know how to gracefully and graciously exit a trustee who is no longer a good fit for the board.
Heads also want chairs to hold space for disagreement so that it can be normalized as part of productive dialogue rather than viewed as personal critiques. Heads ask that their chairs actively participate in scenario forecasting for multiyear financial planning.
Overall, heads felt that the time spent on developing a strong chair-head partnership was extensive but worthwhile. “The more support and cover you provide me, the longer I will last!” wrote one head. Head transitions, especially premature ones, are disruptive to the community, impact enrollment and staff retention, reduce faith in the institution, and derail the school’s mission. A strong head-board chair relationship, however, can help heads navigate through inevitable rough times, lengthening their tenure.