If You Can Keep Your Head: Leading Through the Peaks and Valleys of Headship
Written by SUSAN B. LAir, PHD - TEG SEARCH CONSULTANT & EXECUTIVE COACH
I started my career as a math teacher in 1972. I was 20 years old, freshly minted, and eager to make a difference. Fulton High School (not its real name) was a vibrant place, filled with amazingly talented teenagers, none of whom were particularly excited about factoring polynomials. It was a “low-income” school, and having grown up in the same public district, it broke my heart when I couldn’t find a single math textbook or even a stack of paper in the building. Eventually, I discovered a pile of dusty enrichment workbooks under some old coats in a closet, and off I went, teaching five sections a day, each with 60 students.
One of those students was William. Bright, bold, and always performing, and with sixty students crammed into one room, he had a captive audience. William rose to the occasion!
One day, after he shot spitballs, perched himself on the back of his desk, shouted across the room while I was teaching, and, for good measure, tripped a classmate trying to walk down the aisle, I decided it was time to call home.
The conversation went something like this:
“Mrs. Webster, I’m calling about William. I’ve tried just about everything, but he keeps disrupting class. Today, he tripped a girl on purpose. I need your help…”
She interrupted me mid-sentence and said, “Hey, do I call you during the summer? Good luck, Mrs. Lair.” Click.
I spent six fabulous years at Fulton High School. Math may not have been William’s favorite subject, but he grew up to be an outstanding attorney, and I’m fairly sure he hasn’t had to factor many polynomials since his days at Fulton.
Thus began my journey to headship.
The first, and perhaps most important, thing I want you to understand is this: people will, on occasion, be lunatics. Especially when it comes to their children.
As Head of School, when you inevitably encounter one of these moments (and you will), your job is to take a breath and silently repeat: “If I can keep my head when all about me are losing theirs and blaming it on me…”
Boards Can Be Your Greatest Ally—or Your Toughest Audience.
One of the great privileges of my work today is helping Boards grow into their most important responsibility: hiring a talented Head of School, and then supporting, guiding, and evaluating that leader as the head manages the day-to-day operations of the school.
It’s not unusual for Board members, many of whom run their own businesses, to instinctively drift into operational matters. After all, they’re used to managing details. But schools are different. And when trustees misunderstand the boundaries of their role, they may overstep into areas that belong squarely to the Head and the leadership team.
Trustees are most effective when they act as stewards of the school’s long-term health. They should see themselves as protectors of the school’s mission and future, constantly scanning for financial threats—deferred maintenance, cybersecurity risks, legal exposure, programmatic needs, enrollment trends, and investment challenges.
If you haven’t faced at least one of the following situations, it might just be your first day on the job:
A trustee requests that their child be placed with a specific teacher.
A trustee attempts to influence a hiring or firing decision.
A trustee gets cornered at a social event and promises a parent they’ll “look into” a grading concern.
A trustee pushes for a specific curriculum or advocates eliminating a course.
A trustee questions why a certain teacher remains employed or asks to observe classes.
A trustee scrutinizes minor expenses, like classroom supplies, instead of focusing on broader financial oversight.
A trustee intervenes in a disciplinary matter involving their own or a friend’s child.
A trustee publicly criticizes a school decision, creating confusion or controversy.
These challenges are not only common; they're predictable. And preparation is your best defense.
Strengthening Governance: Proactive Strategies
1. Change the Way Board Meetings Work
Transform routine meetings into opportunities for meaningful dialogue. Replace endless committee reports with a consent agenda, freeing up time for generative discussions, open-ended conversations about strategic priorities. Many of the scenarios above make excellent generative topics, offering you the chance to build trustee understanding of school processes grounded in best practice.
2. Improve Board Composition and Expectations
Work with your governance committee to refine recruitment and onboarding:
Set limits on the percentage of current parents on the board.
Develop a Board Profile outlining needed experience and diversity.
Draft a Trustee Job Description that emphasizes the head’s role as CEO. Include board talking points to ensure unified, mission-aligned communication.
Clarify expectations for continued service and trustee removal, if needed.
3. Create a Head Support and Evaluation Committee
Establish a Head Support and Evaluation Committee that meets regularly. This group serves as both a sounding board and a leadership partner, helping the head navigate challenges while leading an intentional, structured evaluation process.
Parents Are Passionate—As Parents, So Are We
It always amuses me when someone says, “I’m taking off my parent hat now.” That’s not possible, and honestly, it’s not necessary. As heads of school, we deeply value the passion parents have for their children. It’s the most human thing about them.
When I think about what’s best for students, I often ask: What would a thoughtful, loving, balanced parent want or do right now?
Being a parent is a beautiful thing. Being overly demanding? That’s a different story.
For parents, the stakes feel high:
They are investing deeply in their child’s education.
They may feel pressure to see their child attend a prestigious university.
They want the best: academically, socially, and athletically.
But in their desire to do right by their children, parents sometimes need help understanding what children actually need to thrive.
Global Truths for Parents to Hear
1. Grades in Elementary School Are Not Predictors of Future Success
Childhood is for learning how to learn, not for earning perfect marks. A second grader struggling in math is not doomed. They are building resilience, discovering how to ask for help, and developing problem-solving skills.
Scenario: A parent pushes for a grade change after their child receives a B in math.
Response: Trust grows when school policies are clear and consistently followed. Have firm grading policies in the handbook and stick to them. Reassure the parent that learning growth matters more than letter grades in early years.
2. Not Everyone Can Be the Star—But Everyone Can Find Joy in Effort and Play
Falling off a bike. Losing a game. Forgetting homework. Failing a test. These are essential childhood experiences. If we rescue children from every setback, we rob them of the ability to bounce back stronger with pride.
Scenario: A parent is upset their child didn’t make the A team or isn’t a starter.
Response: Reaffirm your commitment to fairness by pointing to clearly defined policies for participation and competition. Emphasize the broader purpose of athletics—confidence, wellness, teamwork, and joy.
3. Not Every Teacher Will Be Your Child’s Favorite—And That’s Okay
Children must learn to work with people they don’t immediately connect with. A teacher your child doesn’t “like” may be the one who challenges them the most to grow.
Scenario: A parent insists their child be moved out of a class due to personality conflict.
Response: Consistency is critical. Follow your school’s protocol and gently explain that learning to navigate different relationships is a vital life skill. Share how the school monitors class environments to ensure every child feels safe and supported.
Teachers Want to Feel Valued—And They Deserve It
Teachers are the heart of every school. They want to feel respected, supported, and fairly compensated, and they should. School leaders must approach these needs with transparency and trust.
1. Compensation: Transparency and Trust
Share the school’s operating budget annually with faculty.
Explain how salary decisions are made and what constraints exist.
Keep employees informed about long-term strategies for improving pay and benefits.
2. Autonomy Within Alignment
Autonomy matters, but coherence matters more. Schools cannot run on “Second Grade According to Mrs. Harper” or “Shakespeare According to Mrs. Perry.”
Ensure vertical and horizontal alignment of curriculum.
Use committees to make collaborative, mission-aligned decisions.
Once adopted, expect all faculty to follow agreed-upon practices.
3. Accountability and Growth
Every educator should be held to high standards and encouraged to grow.
Use a fair, transparent evaluation process with built-in feedback loops.
Make it a conversation, not a compliance exercise.
Promote professional behaviors: collaboration, initiative, adaptability, and integrity.
A culture of growth benefits everyone: students, teachers, and the school.
Closing Thoughts
As heads of school, we must stay grounded, manage stress, and regularly rediscover the joy that brought us to this work. There will be times, as Kipling wrote, when “people will doubt you... and make allowances for their doubting, too.”
But when boards, parents, and educators come together with trust and mutual respect, we give students the greatest gift: the chance to grow into capable, compassionate, and resilient adults.
