This article appeared as "Perpetual Notion” in the Summer 2022 issue of Independent School. When I joined the board of a local independent school in 2003, I thought it would be a great way to get more involved in my kids’ education. Not having attended an independent school myself, I knew little about the decisions that I would be required to make. But given my background as a journalist, I naively assumed that it wouldn’t be hard to gather all the necessary information and figure things out. I was wrong. It turns out that I had quite the learning curve ahead of me, one that caused me to think quite deeply about the ways in which boards and heads communicate and that took me even deeper into the independent school world. But until I joined a school community as an employee, I had a limited perspective—that of a board chair trying to do the right thing. Now, working for a school at the right hand of the head of school, I have a much more complete view. K–12 education is now in the rearview mirror for both of my children, and I’m well established in a second career in NAIS schools—as a chief communications officer at one school and a trustee at another. Along the way, I have made decisions on school policies more times than I can count. I’ve worked for heads who were new in their jobs, mid-career heads, and seasoned heads who had already held senior positions at other schools. And I’ve seen time and again that effective and persuasive communication is the key to a head’s success—especially in relation to the board. While every new head has had bosses before, few heads come from industries where they are reporting to someone who has likely not had paid employment in the same industry or occupied the same kind of position elsewhere; heads may be effectively reporting to people with whom they have little in common careerwise, and who have only a consumer’s understanding of the field to which the head has devoted their life’s work. Whether trustees are drawn from alumni councils, are current parents who lead major industries in the school’s community, or are long-standing school volunteers, they probably don’t speak an educator’s language in the same way that a head does. They may be accustomed to evaluating businesses with metrics that are not reproducible in the school environment or receiving reports on activities that are far beyond their purview. Trustees may also be used to a certain degree of deference or acquiescence if they are leaders in their own field, and they are often not fully prepared to manage someone who is a CEO in their own right. A board chair, for example, might be unclear about what they need to know and when they need to know it. Or a head might be unable to explain why business metrics don’t map easily onto schools. And heads and boards might be reluctant to name and navigate the innate power differential between school employees and members of the board of trustees. Add in the fact that the board chair functions as the head’s boss while also representing the many other people who are involved in the head’s evaluation, and it’s not surprising that 42% of heads and nearly 33% of boards reported having a strained head-board relationship in the past 10 years, according to the 2020 NAIS report “Head Turnover at Independent Schools: Sustaining School Leadership.” Whether they’re at the start of their journey in headship, working through a change in board leadership, or managing dysfunctional patterns of communication that are deeply entrenched in board culture, there are several strategies heads can use to effectively engage the board, build trust, and establish a lasting and meaningful relationship with trustees built on shared goals. When it comes to managing head-board communications, it’s what you say and how you say it. Nurturing the Primary Relationship A head may work with several board chairs over the course of a career at one school, and the first order of business when establishing each new relationship should be to discuss how, when, and what they’ll communicate. Is the board chair a texting enthusiast, or do they want every email written like an old-school memo? Do they want weekly meetings in person over coffee, or will a Zoom meeting as needed suffice? It’s helpful to remember that, like students, different trustees have different learning needs. While one may want to only see charts and graphs, another may want to hear stories of student impact, and yet another may think the most important matter is whether the institution meets a certain strategic planning goal. Heads should let the board chair take the lead in deciding what type of communication vehicle to use. As long as the frequency and content serve the needs of the school and the partnership, adapting to the board chair’s communication style will set a more collaborative tone. In my six years as a board chair working with three different heads, I used a variety of ways to keep in touch with each one. My goal in working with an interim head and a new head was to provide counsel while briefing them on the school’s culture, and so we always met in person so that we could establish trust quickly and get to know each other better. Just seeing how the heads were decorating their offices or watching how others approached them in the school gave me important insight and helped us work together. With a seasoned head, I was learning how to be an effective board chair and encouraging her to make her decision-making process more visible to the board and more inclusive of trustees’ advice. Our meetings, in person or on the phone, followed her lead (like a briefing from a seasoned CEO) and often centered around me helping her understand how to best communicate with the trustees or families. I found that in all cases, however, a weekly meeting was a must to ensure that board chair and head remain well-aligned. I often said in my board chair role (as well as in my staff communications role) that there should be no daylight between me and the head of school. A weekly meeting (preferably via Zoom or in person so as to gauge body language) helps provide crucial feedback to the head and gives the chair an opportunity to voice critiques without it becoming a big deal. As important, it gives the head an opportunity to share small wins that might not make it into a board report. Bart Erbach, president of Erbach Coaching and a strategic communications expert who has served in board leadership for many educational institutions, stresses that heads should use those meetings to proactively communicate successes as well as challenges. “There can be a tendency to go to your chair with problems and more problems, but it’s important to let them know regularly about good news and accomplishments—such as an inspiring story about a student or faculty member. Board chairs are volunteers so they, of course, like to know that their efforts are having a positive impact.” Heads must also understand what the chair needs to advance their own leadership skills. A first-time board chair is likely to be somewhat intimidated. Although I didn’t become board chair until years into my tenure on my first board, I still remember the butterflies I got when anything difficult needed to be discussed. I appreciated that the school’s seasoned head was able to allow me to gain the experience necessary to be the kind of leader that our school needed—rather than subtly taking over in such situations. Although she had much more experience in board work than I did, having served as a trustee herself in other institutions, she always made sure to tell me how much she appreciated my taking the reins in board conversations when needed, and, as important, she never made me feel as though I was needed simply to rubber-stamp her decisions. She also taught me the value of deeper listening, rather than attempting to short-circuit conversation when trustees did not agree. Similarly, a board chair, together with the trustees from the search committee, can help a new-to-the-role head assume the mantle of leadership by encouraging fellow trustees to wipe the slate clean and not make any comparisons to the previous officeholder. They can also help a new head by sharing honestly about trustees’ behavior and temperament in the boardroom and outside, and they can advise the head on how to best communicate with individual trustees—for example, whether they are more likely to be influenced by data or narrative. By observing how the chair works with others in the boardroom, heads can provide simple advice without being overbearing or appearing presumptuous. When a board chair is new to the role, they may find fellow trustees relating to them differently than before and perhaps even challenging their authority in subtle ways. A seasoned head who has almost undoubtedly seen these trustees in more situations than the chair—particularly if the trustees are also parents—can help guide the new chair in how to gain authority and consensus in the boardroom, understanding that it’s not one-size-fits-all when dealing with many different people around the table. Chairs should do the same for heads, reminding them that it’s particularly important to take a step back and listen, even at times when it may appear as though their judgment is being questioned. Establishing the Foundation When I started working in independent schools, I was surprised to find that board orientations beyond discussion of donations, meeting schedules, and other logistics weren’t always standard fare. But clearer communications between heads and boards starts with giving trustees a complete job description and an orientation to go along with that job description. For example, Stevens Cooperative School (NJ), where I served as board chair, had a parent-elected rather than a self-perpetuating board (a quirk of its founding as a cooperative school), so we knew that orientation was particularly important, lest our trustees think that they were representing the folks who voted them into office. “A good orientation guides trustees on how to work on committees and helps them understand the appropriate role for a trustee so that when they walk into a board meeting or other rooms, they are clear which hat they’re wearing,” says Pollyanna Inc. founder Casper Caldarola, who was a trustee at The Dalton School (NY) for a decade and the communications director at The Allen-Stevenson School (NY) for almost twice as long. NAIS’s Principles of Good Practice for boards and for trustees can provide needed structure to such discussions and can also be useful tools for annual retreats, which, in addition to providing time and space to discuss high-level issues, should also act as a refresher on board culture. If trustees are initially skeptical about the importance of training, heads can respond that a proper orientation will clearly delineate their duties and responsibilities and ultimately make more efficient use of trustees’ time overall. When I was a new trustee, I struggled with boundaries—not between my role as a parent and a trustee but rather by sometimes assuming a quasi-administrator role helping with communications for people who were very aware that their boss reported to me. A more thorough orientation would have given me a better understanding of when I should offer advice and counsel instead of stepping in and doing the hands-on work. Despite solid training, sometimes trustees run afoul of their roles and need to be reined in. I’ve seen this happen particularly around curriculum, where the trustee, rather than asking for clarification on the course, instead launches into whether a certain book is appropriate for sixth graders or whether health education for lower school students should include a discussion of sex. As a board chair, I’ve even seen a trustee attempt to use a board meeting to advocate for a particular teacher whose contract was not being renewed. When a head notices that things are going down a bad path, they should point it out to the board chair right away. The chair, perhaps acting with an executive committee member, is responsible for correcting the errant trustee. Sometimes, however, chairs are hesitant to perform this crucial role because it is extraordinarily awkward. This could happen because the trustee in question is a major donor or because the trustee is a close personal friend of the chair. In such cases, heads may have to use their powers of persuasion and stress the ways in which the misbehaving trustee is not only affecting board culture but also making the board less efficient in its work. Bearing Bad News Reporting bad news, whether it’s disappointing enrollment numbers or the discovery of a long-term teacher who has had inappropriate boundaries with students, can test the head-board relationship. Yet it can also strengthen that relationship in ways that will pay dividends through good times as well as challenging ones. When it comes to problems, nobody likes surprises, especially trustees, says Duby McDowell, principal of McDowell Communications Group, who has advised and guided many independent schools in their crisis communications. “Heads of school who are scrupulous about keeping the board chair informed tend to be successful,” McDowell says. Trustees can become prickly when they are kept out of the loop. “It’s ideal if the head and the chair work together during a crisis because boards can ‘leak,’ so sharing confidential matters with the entire group can be risky. Board members usually accept the formation of a small, working committee that focuses on the crisis in concert with the school’s legal counsel. With the committee in place, the larger board feels it has been represented while the crisis was managed.” The key to sharing any disappointing news is imparting a clear understanding of why the situation occurred and what might be done to mitigate any damage. As both a trustee and a communications professional, I know spin when I see it and am less interested in looking at the positives of a negative situation than in hearing about corrective actions and the lessons learned. When I was a board chair, I always appreciated the opportunity to hash out tricky situations with the head—such as employment issues or a difficult situation with parental behavior—with the full understanding that the head didn’t have to take my advice. It’s always helpful to both chairs and heads to talk briefly before any crucial strategic discussion at the board level and role-play how it might go. This is the time for both of them to think about the ultimate goal of the discussion and how to guide the board along a path toward that goal. Managing for Success It’s crucial for a head to be able to “manage up” to trustees—particularly in this age of sudden pivots, whether due to COVID, DEI issues, or other concerns. When coming to the board for a quick or potentially controversial decision, heads should present the case in a way that will allow trustees to have all the facts and not feel unduly rushed, even if the matter may indeed be an emergency. Heads of school can serve a board—and thus the school—by best framing the needs of the school in ways a board can understand, with relevant data, Erbach says. “If you need a specific vote on something for a specific reason make it all clear; pull all of the relevant information together.” I always felt most comfortable advocating for change with my fellow trustees when a head presented me with all of the potential pitfalls of a decision, including a well-considered Plan B in case things didn’t work out. Of course, the time to start the managing up process is when trustees are joining the board or, in the case of new heads, during the first few months after they have joined the school. All trustees will have hot-button issues that they are deeply interested in, such as real estate, fundraising, faculty development, or DEI. Being able to nurture those interests through appropriate committee placement or requests for advice is an art, especially since the head needs to make sure that trustees do not stray from their domain. Trustees can bring deep expertise to the table that school administrators will not have, but, at the same time, they must be led to understand that school business isn’t the same as corporate life. Trustees also need to view the school administrators who are part of board discussions or present during meetings as experts—and heads must work to ensure that the board sees that they surround themselves with great teams. Sherri Bergman, director of communications at St. Andrew’s-Sewanee School (TN) and a trustee at Linden Waldorf School (TN), worked for a head who knew exactly how to make that happen. “He required a tremendous amount of preparation for board meetings, including making sure that we had our reports finished well ahead of time and that the staff who would be in the board meeting had seen them,” she recounts. “We had an opportunity to ask our questions before the board meetings and in practice meetings where we would anticipate what a trustee might ask. Following those pre-meetings, we would build those answers into the presentation, or when those questions came up, we had great responses.” Getting Helpful Feedback Heads also need to solicit honest and helpful feedback from trustees and, in particular, ensure that the head’s annual goals—often co-created by the head and the board— are reasonable and measurable. Unlike corporations, which may have very specific structures to scaffold evaluation and compensation, schools and boards may not be as thorough in following through with a yearly feedback process. That can often be the case if the head’s contract already outlines the compensation structure. Bergman recommends that heads consider asking the board to work on developing clear metrics to gauge their performance, noting, “Heads could frame this by saying, ‘There are lots of different things I could be working on so I want to make sure our priorities are aligned.’” If a board and its members don’t sharpen their evaluation skills when things are going well with a head, she warns, it’s much harder when things get difficult. Even when an evaluation is quite good, trustees can be shy about pointing out areas of improvement for senior heads when they aren’t sure how those heads will accept the critique. The risk, however, is that such challenges assume an outsized importance when something goes wrong simply because they weren’t discussed in the past. Suddenly, what was a small issue that might have been solved by coaching turns into a major problem that threatens the fundamental partnership of the head and board. That’s why it is so important for the head and board chair to have regular meetings, even if they only have a brief agenda. It creates space for these conversations to happen naturally and creates an atmosphere that consistently reminds senior heads of the board chair’s supervisory role and helps the board chair—who may have thought of the head primarily as a leader, not a partner—gain comfort in resetting that relationship. I have been fortunate to work for heads who have trusted me to provide advice on communicating productively with their boards. I remember speaking to one head about how scared I felt on becoming a new chair. He was shocked because he hadn’t considered that his own new board chair at the time might have felt this way also. For perhaps the first time, he considered that they had more in common than he had thought, and he gained greater empathy for the stresses inherent in being a parent-leader in a day school. Ultimately, good governance is the bedrock upon which our schools and their missions rest, and the key to that is establishing a productive partnership between the head and the board. While good communication can’t solve every problem, it is often at the root of many of them. Whether advancing an agenda or heading off a firestorm, mastering this art will serve a head of school well throughout their career.