How It Started

I never planned on being a Head of School. I was quite clear, when anyone asked, that when it came to school leadership I wanted to be the stage manager, not the director. I did not want the buck stopping at my table; I wanted to be the one telling someone how to spend or save the buck. With fourteen years at one school and 22 years at another, in the role of Assistant Head and Division Director, I loved my sweet spot. But then an opportunity presented itself at just the right time in just the right way, and I had an opportunity to lead a school I had known for several years.

I began my first (and only) Headship in the depths of COVID: summer, 2020. When I was appointed in October of 2019, I was charged with certain initiatives, all of which I was enormously excited about and all of which seemed hopelessly naïve nine months later. For example, “create meaningful opportunities to get the families into the school more often” – which during COVID would prove impossible.

In the next five years, I learned more than I ever thought possible and realized how very little I actually knew. It was like my first-year teaching all over again. From being too friendly to being overwhelmed by every detail to not understanding what I was sure I knew, the first year of teaching and the first year of headship were remarkably similar for me.

What I Know Now

Headship grows harder every decade, every year. And this field needs talented leaders. It may be impossible to avoid the classic pitfalls of that first year for those new to headship, but with the gift of distance I humbly offer the 10 things I learned as a first time Head of School that I wish I knew from the start.

1. The Vision Thing

Vision cannot be underestimated or overstated. I knew what I believed in, I knew what I stood for, and I thought I communicated it well. But blog posts and speaking events are only part of demonstrating vision. 

Next to the mission, as Head you need to live your vision every waking moment. Too often, I would be flummoxed when it came to priorities, all of which seemed immovable. There were pressing budgetary needs, enrollment concerns, marketing and communications initiatives, program opportunities, staffing goals, and many more. I read once that while every director, head, or chair in your school has 1000 worries about their program, the Head of School has 1000 worries about every program. How to sort it all? 

When you know your vision for your school, you know what needs to be prioritized. Even if, at times, it is heartbreakingly hard.

2. Do Not Doubt You Know Best

You are hopefully blessed with a wise and thoughtful administrative team, and if you are wise and thoughtful, you listen to them and work closely with them. Still, you are sitting in your chair for a reason. You have a unique and singular lens; know that as Head, you are trusted to know best.

3. Never Assume You Know Best

What I wrote above? It’s true, but – always remember that you have a unique and singular lens, and it can get cloudy at times.

4. What Delegation is and What it is Not

As Head, you must remain at 30,000 feet. You need to see the whole landscape. Yes, you can do many other people’s jobs. And if you do, you are not mentoring them, you are failing to do yours. 

5. You Cannot Communicate Too Much

Like the vision thing, when it comes to communication, clarity really matters. For someone who prides herself on her ability to speak clearly and powerfully, too many times my words were met with dead silence, confusion, and frustration. Practice and rehearsal can help. Spontaneity and sincerity do not always land the way we hope.

6. You Can Over Communicate

Sometimes, you just have to let the thing be done. There is a difference between reinforcement and repetition.

7. What Relationships Are

Be careful of boundaries. Work friendships are as fraught as they are tempting. Sharing personal thoughts with a direct report on Monday can backfire when you need to provide critique on Tuesday.

8. Clear is Kind 

Brené Brown is correct, and for those who are not comfortable with confrontation, take this phrase to heart. Making someone feel better about a bad decision, a poor choice, or a difficult moment is neither clear nor kind, or in any way supportive. That said, there are those who love to quote this as an excuse for being genuinely unkind and unnecessarily blunt.

Clear is kind. It is not mean.

9. Bullies Do Exist

I admit it. I myself do not like confrontation. I was once told that this would make the job of headship harder, and it’s true, it did. But I have been fortunate. I have dealt with two genuine bullies in my professional life. I knew when I was being gaslit but did nothing about it. I thought it was my job to rise above bad behavior, not address it.  I was wrong. Addressing it is also rising above it.

10. Boards and Headships Have Changed 

I thought I knew what my job would require – guiding everything from Admissions to fundraising to supporting and educating families and colleagues and making sure I had a good grasp of budget and priorities. I wanted to be in classrooms, doorways, lobbies and events. I wanted to know every family and every colleague’s story. As the Head of my school, I would love it as I love my own family.

But during COVID, I spent more time doing what I did not know and not nearly enough time doing what I knew and loved. That was not unique. It was true for everyone.

Almost every Head I know has said at some point, “Headship has changed. It’s just not the job we all thought we signed up for.” Boards have changed too. And parents, they are always changing. Teachers have changed as well. But all of that is for a different essay.

Paying it All Forward

The saying that nobody has the perspective that the Head of School has and that nobody but a fellow Head can truly understand what it is like to sit in that chair is a fair one  – and one I originally scoffed at. But,it is true. And that is perhaps the 11th point.  So, find those trusted colleagues and lean on them. And one day, share your mistakes and your wisdom with other future Heads. We will be here with a very unique lens.

Future and aspiring Heads: be clear and loud about your vision, be brave and sensitive about clear communication, stand up for what matters and for what you know. 

Be you! 

Be the Head of Your Team.  

You. Are. The. Head.