What My Tears Taught Me About My Leadership

Yes, I’m playing into the stereotype: a new leader finishes their first year in leadership and writes a reflection.

I actually wasn’t sure if I would do it.

Did I reflect and learn things about myself? Absolutely.

Did I think sharing those reflections publicly was a good idea? I wasn't so sure.

So I slept on it. When I woke up, I realized that ten years from now I might not remember this moment, how significant it felt, or even what my biggest lessons were. So I’m writing. For myself, first and foremost. But perhaps something here will resonate with someone else too.

Let's Talk About Tears

A few years ago, I attended a women's leadership luncheon. Somehow, the conversation turned to crying in leadership.

I remember two women sitting across from me explaining that, in their experience, tears were something they couldn't afford. Showing emotion, they felt, risked being perceived as weak.

I remember feeling challenged by that perspective. I said something along the lines of, "Why should crying be seen as a sign of weakness in a leader?"

The response was thoughtful but discouraging.

"You're right," one of them said, "but that's a huge risk you'd have to live with."

I left that luncheon disappointed. Was that really the future for women aspiring to leadership? That we would have to choose between being respected and being human?

About a year and a half later, I was serving on an accreditation visit and had the opportunity to meet several inspiring and accomplished female leaders. During our final lunch together, the topic of women in leadership surfaced again, and once again the conversation drifted toward emotion and the expectation that leaders hide it.

This time, however, I realized I knew exactly where I stood.

Emotion is part of what makes us human. Why should I have to hide my humanity simply because I am in a position of leadership?

I decided then that I would not.

I can be human and be a strong leader. I shouldn't have to choose between the two.

What My Tears Taught Me

When I look back on my first year in leadership, my biggest lessons came from the moments that brought me to tears.

I've come to realize that those moments deserve my deepest reflection because they reveal what I truly value. They are signals pointing toward the things that matter most to me as a leader.

This year, I cried only three times.

The first two taught me the same lesson:

I deeply value inclusion and belonging.

The first time I cried was when one of my efforts to include minority members of our school community came under attack. What hurt was that in my attempt to include others, I found myself feeling excluded and blamed for being insensitive. What hurt even more was that the criticism came from a group to which I felt I should have belonged.

The second time I found myself in tears was when I was once again treated as an outsider in decisions where I believed I should have been in the room.

Neither experience has diminished my commitment to belonging and inclusion. If anything, they strengthened it.

Those moments helped me understand one of the reasons I wanted to move into leadership in the first place. I want to contribute to making schools more inclusive places. I find myself paying closer attention now to who is being included, who might be left out, and what structures can be strengthened to create a greater sense of belonging.

The third time I cried was much more public.

It happened during my Fifth Grade graduation speech.

I didn't realize until I began reading the speech aloud just how much that group of students had shaped my first year at Green School. They brought joy to so many of my days. There is something difficult to put into words about that particular group, but they helped me understand what makes a Green School student so special.

As I congratulated them, the tears started flowing.

And I let them.

I was overwhelmed with gratitude for the year they had given me and for everything they had reminded me about why we choose to work in education.

That moment taught me something else:

The relationships I build with those I serve matter deeply to me.

Getting to know students and discovering what makes each of them who they are has always been one of the greatest joys of this profession. It is what continues to bring me joy every single day.

There is a special kind of magic at Green School, and our students embody it completely.

This particular group of fifth graders reminded me why this place matters and why the work matters. It matters because we have the opportunity to create environments where young people can grow into who they are meant to become while understanding their role in a larger world and the impact they can have on it.

Perhaps that is the lesson I am carrying forward from my first year in leadership.

The moments that challenge us, frustrate us, break our hearts, or move us to tears often reveal what we value most.

For me, those values are belonging, relationships, and humanity.

As I move into my second year of leadership, I hope to hold tightly to all three. I hope to continue working to creating spaces where people feel seen and included. I hope to build relationships rooted in trust and care. And most of all, I hope I never convince myself that leadership requires me to leave my humanity at the door.

Because if this year taught me anything, it's that the moments that made me cry weren't signs of weakness.

They were reminders of what matters most.