This article appeared as "How to Be a Better Trustee” in the Spring 2026 issue of Independent School.
After more than 20 years as an independent school parent and nearly as long serving as a trustee across nonprofit, for-profit, and cooperative schools, I’ve seen the full gamut of boardroom behavior. I’ve come to understand that much of the unproductive behavior we hear about boards is rarely ill-intentioned; more often it stems from trustees being underprepared for the realities of school leadership.
That became clear to me in a new way when, after serving 13 years as a trustee at a cooperative independent school, I began a second career as a senior communications leader at a different pre-K–8 school. Overnight, I found myself on the other side of the boardroom table, answering questions from my boss’s bosses. Comments I might once have made easily as a trustee now landed as unproductively critical or simply unworkable given real constraints on time, resources, and strategy.
As a school trustee, I had weighed in on teachers’ working conditions or challenged the admissions process without truly understanding what it takes to run a school day to day. I was reminded of this again this past year when I joined the board of the Council for the Advancement and Support of Education (CASE), which serves advancement professionals across colleges, universities, and independent schools. The scope and complexity of issues are far greater than anything I’ve encountered before—and while my decades of experience in schools have been valuable, they are not enough. Many independent school trustees will recognize this dynamic: Professional expertise in finance, law, real estate, or accounting can add real value to certain aspects of board work. But on its own, it’s not sufficient.
True value comes from how a trustee chooses to grow—by listening, learning, engaging deeply with operational reports, and identifying the strategic questions that still need to be answered. Trustees aren’t there to manage administrators; they hire the head of school to do that. Instead, their role is to protect and guide the institution with vision, discipline, and unwavering fidelity to the mission it exists to serve.
And it is in that spirit of mutual respect for expertise, honest self-awareness, and disciplined commitment to staying in your lane that I offer 10 tips for being a better trustee.
A little humility goes a long way.
It’s natural to feel honored when you’re asked to serve as a trustee. Your school’s leaders see you as someone with strong experience, judgment, capacity, or the ability to advance important financial goals—or perhaps a skill set others on the board don’t share. But regardless of what you brought to the table, and no matter how well you think you know the institution, the role carries an obligation to learn as much as it does to lead. Your most meaningful contributions come not from applying familiar expertise reflexively but from developing a deeper understanding of the school—and from viewing it through a different lens: safeguarding the mission for the long-term benefit of future generations. The work requires patience, humility, and a willingness to have long-held assumptions challenged.
Positionality matters.
Before I worked for a school, I didn’t fully appreciate that when administrators entered a boardroom, they no longer saw me as a longtime volunteer or friendly neighbor. They saw me as their boss’s boss—and approached the moment accordingly. Administrators are keenly aware of the power that trustees hold. It’s therefore incumbent upon trustees to help school leaders be their best when they are sharing the information the board needs to govern well. A warm, professional demeanor matters, as does explicit respect for educators’ expertise and a sincere appreciation for work well done.
Training shouldn’t stop after orientation.
Many trustees attend required orientations and retreats but stop there, even when regional and national associations offer professional development that would make them more effective in the boardroom. I participated in some trainings as a board chair, but I came to fully appreciate their value only after I began working in schools, where ongoing learning for adults is expected and encouraged. Your professional and life experience may not map neatly onto school operations in ways that are most helpful. Thoughtful, targeted professional development will help bridge that gap.
School is not just a business.
Unfortunately for educators, there’s a persistent societal belief that what happens in schools doesn’t require deep technical or intellectual expertise—hence the tired refrain, “Those who can’t do, teach.” While most trustees would reject that idea outright, it can still show up in practice: an overreliance on suggestions that might succeed at a multibillion-dollar hedge fund but fall flat with an experienced teaching faculty, or with parents and students who are each, in their own way, the customer. Schools are complex ecosystems, and many outcomes for students lie beyond any one adult’s control. To be an effective trustee, you must immerse yourself in the realities of the independent school environment. Ask your head of school about resources that will help you better understand the issues school leaders are navigating today.
Understand and be aligned on the school’s KPIs.
Many boards have received thoughtful, detailed reports from a director of college counseling, only to hear a trustee ask, “How do our Ivy results compare to our competitors—and how do we get closer?” While the question reveals what one trustee values, it can be deflating for an administrator who has spent countless hours building a program that likely does not define success in that way. Versions of this misalignment appear across every area of school life. One of my favorites was a suggestion to use billboard advertising to entice families stuck in traffic on the way to their child’s current school—completely at odds with a carefully developed strategy focused on targeted outreach to likely prospects. Effective governance depends on alignment: The metrics administrators report on should flow directly from the goals the head has presented to the board—and that the board has agreed to—each year.
Take off your parent hat.
While it’s natural to put your child first, the boardroom—or private conversations with the head about school business—is not the place to do that. When I facilitate trustee training, I often use a case study in which the board is voting to sunset a program a trustee’s child loves because it no longer serves the school’s needs. I’m always surprised when a new trustee in training says they’d try to find a workaround even after learning the best practices to navigate the scenario. I’m equally troubled by stories about trustees using their position to pressure heads of school or senior administrators in private. These accounts circulate widely among school administrators, and I’ve had to address them myself as a board chair. Trustees should pause and ask: How would this feel if our roles were reversed? Am I rejecting the decision on principle, or simply because I don’t like it? And is what I’m doing truly in the best interest of the school? Honest answers to these questions usually make clear when a trustee has crossed a line.
Your board service is not for public consumption.
No one expects trustees to keep parent friends at arm’s length about everything, but what’s said in the boardroom must stay in the boardroom. Over time, boards will make unpopular decisions or discuss sensitive matters involving students or personnel that require strict confidentiality. It’s also common for parents to ask trustees to “take something up with the board.” When I was a board chair, there were some trustees who constantly fielded these questions or requests from friends; others virtually never did. I think the difference was that the unbothered trustees had clearly defined their board role—and held firm boundaries when tested. For the sake of the school, your fellow trustees, and the head of school, it’s essential to make clear that you are that trustee with firm boundaries.
Maintain a united front with your head of school.
As a board chair, I told a new head of school from the outset that there would be no daylight between us and that he could count on my full support with the board or with the community, regardless of what we discussed in private. While I have rarely seen trustees undermine heads overtly, I have seen the more subtle damage that’s caused when a group decides to “ambush” a head at a board meeting over a point of disagreement. This is where the rule of no surprises matters. If you plan to raise a contentious issue, give the board chair advance notice so the head of school can come prepared. A united front in public is not about avoiding hard conversations—it’s about having them in the right place, at the right time, and in service of the school.
What you say—and how you say it—really matters.
One of the most useful facilitation norms is WAIT—Why am I talking? It’s a valuable reminder for trustees to ask themselves. We are all responsible for collaboration in the boardroom, and unless we are in executive session with no staff present, we are rarely speaking in isolation. Even when a question is well-phrased and genuinely relevant, trustees should pause to consider whether it advances the larger discussion or is better raised with the head later. If something seems missing from a report and requires full board attention, the appropriate route is through the board chair, who can consult with the head of school. It remains the head’s decision whether to broaden an administrator’s presentation.
Your board chair has a hard role—don’t make it harder.
When you join a board, you may not realize how demanding the role of board chair truly is. The chair not only leads the board; they serve as the main representative of the board to the school and broader community while managing a constant, high-stakes relationship with the head. While the head reports to the full board, many sensitive issues—personnel matters, emerging challenges, outside incidents—are handled first, and often only, through the chair.
During my six years as a board chair, I fielded daily calls and emails from heads as well as trustees sharing a wide variety of information while also managing these trustees, committees, donors, and board business. Many new chairs, even those with years of board experience, receive little preparation for this workload. What they don’t need are trustees who bypass protocol, are indiscreet with board business, politicize decisions, threaten to withhold support, or seek special treatment. Respecting the chair’s role—and not adding unnecessary strain to it—is essential to effective governance.