What Every Head of School Wishes They Could Say to Their Board

By Ruston Pierce
Fundraising & Capital Campaign Manager | Fortify Foundation

“I just wish my board understood what I deal with every day.”  If I had a dollar for every time I have heard that phrase, I could buy a small island in the Caribbean.  Why do school administrators and school boards struggle to communicate in a lot of schools.  The relationship between a Head of School and a Board of Trustees is one of the most important partnerships in independent and Christian school leadership. When it functions well, schools flourish, missions advance, faculty thrive, enrollment grows, and long-term sustainability becomes possible.  However, even in healthy governance environments, there are thoughts that many Heads of School quietly carry but rarely say.

They don’t speak up not because they are ungrateful or because they are frustrated. They don’t speak up because the role requires diplomacy, discretion, and a commitment to institutional health, even if it’s at the expense of the Head.  I believe that if they could speak candidly, many Heads of School might say something like this:

Governance and Management Are Not the Same Thing

One of the greatest gifts a board can give its Head is clarity about roles.  Boards govern. Heads lead. The board is responsible for mission, strategy, financial stewardship, and evaluating the Head’s performance. The Head is responsible for implementing strategy, leading personnel, managing operations, and making the countless decisions required to run a school each day.

When boards begin solving operational problems, directing employees, or revisiting administrative decisions, confusion follows quickly. Faculty lose confidence in leadership structures, accountability becomes blurred, and decision-making slows. Strong schools are built on trust in clearly defined responsibilities.

Decisions Look Different from the Head’s Seat

Tuition increases, staffing changes, or a new program proposal are all viewed differently from the Head’s perspective vs. the Board’s perspective.  The Head sees all those things simultaneously through a lens of managing personalities, additional communications, and possibly controlling negative fallout.  Heads carry enrollment forecasts, parent concerns, faculty morale, accreditation requirements, compensation pressures, donor relationships, facility needs, and strategic priorities at the same time.

The Board does not have to deal with those variables, so they do not always understand that every decision made potentially creates new work for an employee.  A decision that appears simple from the boardroom often involves dozens of competing considerations that remain invisible to everyone else.  Healthy governance assumes complexity before assuming poor judgment.  Boards who understand that the school engages with a lot of continually changing variables also recognize the need for patience with any new changes implemented at the school.

Supporting the Head Publicly Matters

We discuss/argue in private.  Publicly we show a united front.  Questions and disagreements belong in the boardroom. Unity belongs everywhere else.  Faculty members notice when board members publicly second-guess leadership decisions. Parents notice when board members offer private opinions that conflict with school communications. Donors notice uncertainty in institutional leadership.  Boards do not need unanimous agreement to project confidence and alignment.  The strongest boards create space for vigorous discussion internally and unified support externally.

Board Members Do Not Supervise Employees

Teachers should report to division heads or principals.  Division heads or principals should report to senior administrators.  Division heads or principals report to the Head of School.  When board members bypass those structures, even with good intentions, they unintentionally undermine organizational health and the Head.  Schools function best when communication follows established channels and authority remains clear.

The Tyranny of the Urgent is Rarely as Urgent as it Feels

Independent and Christian schools are highly relational environments. Parents are passionate about their children. Alumni care deeply. Donors have opinions. Community concerns often arrive with intensity and emotion.  A lot of the time the intensity and emotion cloud the facts of the situation.  Boards who are not healthy struggle with being emotionally charged in these moments.  However, not every complaint requires immediate intervention.

Sometimes the most valuable thing a board can do is ask, “Has the leadership team had an opportunity to address this through normal processes?”  Patience is often an act of confidence in leadership and models to constituents at large that issues should be handled in a fact-based, calm way.

It’s Lonely at the Top

Many school leaders spend their days carrying difficult decisions that cannot yet be shared, personnel issues that must remain confidential, and institutional risks that others never see.  Sometimes, due to legal reasons, it can never be shared.  Heads take a pastoral role with families and employees a lot more than most board members realize.  It is very common.

Heads will celebrate the school publicly while worrying privately.  If there is a good relationship, the board chair often becomes the only person with whom the Head can speak candidly about the burdens of leadership. However, if that relationship has not been cultivated, the Head can feel very much on an island with information that could lead to depression or feelings of burn out.  Great board chairs understand that one of their most important responsibilities is not governance expertise but partnership, encouragement, and perspective.  A board chair who is a consistent sounding board for the Head might be the most impactful benefit of a board.

Annual Evaluation Should Not Be the Only Feedback Conversation

The healthiest Head-board relationships are built on regular communication rather than annual surprises.  Frequent check-ins create trust.  In healthy schools the board chair and Head meet at least once a month.  Small concerns can be addressed before they become major issues. Expectations remain aligned. Wins are celebrated while adjustments can be made in real time.  No leader benefits from hearing twelve months of feedback compressed into a single meeting.  The board chair should be consistently soliciting feedback from the rest of the board to share with the Head so there is an ongoing appraisal of the Head’s work for growth opportunities.

Recruiting and Retaining Excellent Trustees Is Governance Work

A board’s effectiveness is determined long before a meeting begins.  Keeping quality board members for as long as possible should be every board’s priority.  However, recruiting these individuals should not be the role of the Head.  The quality of governance depends on recruiting board members who understand fiduciary responsibility, embrace the mission, avoid personal agendas, and commit to healthy governance practices.

Board culture compounds over time, both positive and negative.  One exceptional board member elevates discussions. One unhealthy board member can consume disproportionate energy and attention.  Succession planning matters as much in the boardroom as it does in school leadership.

Remember That the Head Is a Human Being

Behind every title is a person.  A person who misses family dinners during admissions season or attends four games and/or arts productions in a week.  A person who receives difficult emails late at night and can feel like they are on call 24/7.  A person who carries responsibility for students, faculty, finances, facilities, fundraising, enrollment, and institutional reputation.  Heads of School willingly accept these responsibilities because they believe deeply in the mission of their schools.

But encouragement matters.  A brief note or text message after a difficult decision, a word of appreciation after a successful event, or a simple acknowledgment of faithful leadership can have an enormous impact.  It sends the message to the Head that they are not alone.  Leadership is demanding work. Gratitude sustains leaders longer than criticism ever will.

The Conversation Every Great Board Eventually Has

The best boards eventually arrive at a simple realization.  Their primary responsibility is not to run the school.  Their primary responsibility is to ensure that the school has the leadership, resources, and strategic direction necessary to fulfill its mission for generations to come.  When a board trusts its Head, supports healthy governance boundaries, and commits to partnership rather than supervision, remarkable things happen.  Schools become healthier.  Leadership becomes stronger.  Mission advances faster.  Both the Head and the Board can focus their attention where it belongs: serving students and stewarding the institution they have been entrusted to lead.