HomepageISTEEdSurge
Skip to content
ascd logo
Log in to Witsby: ASCD’s Next-Generation Professional Learning and Credentialing Platform
Join ASCD
October 21, 2026
•
5 min (est.)
ASCD Blog

The Unexpected Challenges of Becoming a School Leader

author avatar
A veteran teacher turned administrator reflects on the loneliness of her new role and the strategies that helped her find her footing.
School & District Leadership
A woman standing alone on a pathway in a desert
Credit: Jorm Sangsorn / Shutterstock
As a teacher for 11 years across three schools, my relationships with colleagues always came naturally. But when the next decade of my career took me to administrative positions, I felt an unfamiliar vulnerability. My training had prepared me well for the professional tasks of my administrative roles, but not for challenges of navigating collegial relationships, managing institutional change, and learning a new school culture.
Sometimes I wondered if I was the only leader who felt this way, but I’ve realized that feeling a bit out of your depth is all part of the process of becoming a leader. And I’ve learned strategies for coping with these growing pains.
When I was a new teacher, you could usually find me during my free periods gathered with colleagues and venting about this class or that admin. I deeply appreciated having colleagues I could confide in and a work bestie who would pop in with an iced coffee for a complaint session when I needed it most. My job was hard, but I almost never felt lonely. When I stepped into an administrator role at a new school nine years ago, I experienced a profound shift. There was no longer a common “enemy” to complain about—I was now the “them” in the “us vs. them” dynamic.
Faculty come to me when they’re excited to share something they’re working on or have a problem they need help solving, and I always try to close my laptop and be present with them. However, I have to enforce boundaries when conversations veer into venting.

Once I became a leader with decision-making authority, I realized that some of the decisions I had rolled my eyes at as a teacher were more complicated and nuanced than I gave credit for.

Author Image

Eating lunch at the teacher table once in a while gives me a chance for informal interactions, although I excuse myself when it’s clear teachers just need to complain to colleagues. I don’t want to put teachers in an awkward position. However, I can connect personally with my teacher colleagues through shared interests, trading stories about pets and families, or laughing at silly memes.
I’ve found the camaraderie and trust I valued as a teacher, but it looks different now. The colleagues with whom I can blow off steam and speak more freely are people at the same level of leadership as me or from other areas of the school with whom I have less direct daily interaction.

Managing Change

Once I became a leader with decision-making authority, I realized that some of the decisions I had rolled my eyes at as a teacher were more complicated and nuanced than I gave credit for.
When I transitioned to a new school and a new leadership role, I immediately started planning for the mid-August faculty in-service meetings. With my newly completed doctoral program under my belt, I knew all the right moves. I listened, I collaborated, and I built on what already existed before me.
But I quickly hit on a common conundrum: If I only tweak the system created before I got there, I get negative feedback about decisions I didn’t make. On the other hand, if I scrap what’s already there to start fresh, suddenly people hold tightly to how they used to do things. I chose to avoid big changes and tweak the current system.
At the end of my first in-service week, the survey feedback was mixed: I hadn’t knocked it out of the park, and more than one person (including my boss) commented on small changes that I didn’t think anyone would notice. In fact, the negative feedback I received involved aspects of the program that I hadn’t changed. I realized that my decisions as a new leader came with a new kind of scrutiny, and even changes that seem minor to me will feel like a major departure to some. I no longer try to pretend I haven’t changed something when I have. I’m mindful of it, but it doesn’t stop me from doing what I believe is best.
I have found that when I focus on the why—either why I made a change or why I kept things the same—I get more traction with faculty. They want to know that they’ve been heard in the decision-making process, but they understand that there are many competing interests. When I invite everyone to the table, including peers who are most affected by a change, I get more buy-in.

Fitting in Takes Time

Change is difficult enough when you already know a community. Transitioning to a leadership role at a new school has an added layer of vulnerability.

When you are learning new skills, new systems, and a new language, it’s OK to feel confused.

Author Image

As a new employee in my first leadership role, I found myself bombarded with questions that left me wondering if we were even speaking the same language. Are you excited for choosings? What do you lead for tikkun olam? How many bells do you have? As an administrator, I felt extra pressure to “talk the talk” so I could inspire confidence in my colleagues, but that is hard to do when you have no idea what all the school-specific jargon means!
Eventually, I learned that “choosings” was the beloved tradition where I would be selected onto either the “fox” or “hound” team (similar to “houses” in the Harry Potter books); tikkun olam (Hebrew for “repairing the world”) refers to the school’s community service program; and bells means class periods. When you are learning new skills, new systems, and a new language, it’s OK to feel confused. When people forget that you’re new or assume you know their specific lingo, don’t just smile and nod. Stop them and ask for clarification.

You Will Find Your Path

If you’re a new leader feeling some loneliness or uncertainty, give yourself grace. For me, it was sometime in my second year in a new leadership role when I shifted from talking about your school to talking about our school—when I stopped viewing the school as someone else’s institution and began thinking of it as my own.
The transition to leadership takes time, and it requires new skills beyond the job-specific ones that got you the role. The feeling of vulnerability isn’t the most comfortable, but there will be a day when you look around at the relationships you have built and the systems you’ve changed, and you’ll realize how you’ve made the transition from new and uncertain to experienced and confident.

Kristine Varney is an experienced school leader who has taught and served as an academic leader in a variety of school settings for almost 20 years. She currently serves as assistant head for academics at Norfolk Collegiate School in Norfolk, Virginia.

Learn More
Related Blogs
View all
undefined
School & District Leadership
Four Anchors for Framing Equity Work
Terrance L. Green
in 4 days