I still remember my first day as a school administrator at age 34 in Attleboro, Massachusetts. My office looked like a blank canvas, with bare walls, a desk piled high with binders, and a computer blinking with unread emails that I didn’t yet know how to prioritize.
I walked the halls with a mix of pride and anxiety, determined to “get it right” but unsure what that even meant.
Maybe you’re feeling that way right now. Excited. Nervous. Overwhelmed. Confident one minute, second-guessing yourself the next. If that’s where you are, you’re not alone. Every leader has been there.
When I look back on my 20 years in school administration, and through the lens of researching and writing my latest book, NeXGen Mentorship: Ignite, Engage, Excel, I see the many lessons I had to learn the hard way. Some came from mentors, but many came from my own mistakes. Those mistakes shaped me just as much as my successes.
That’s why I want to share, because most of the learning you won’t find in a leadership handbook. They’re the lived, experiential lessons, the kind you discover in real conversations with staff, in late-night problem-solving, and in those moments when you realize you don’t have all the answers.
Today, as the Assistant Superintendent of Technology & Learning in New Bedford Public Schools, I carry these lessons with me daily. If I could sit across from you, seltzer in hand, here are seven truths I wish I had known when I first stepped into this role.
1. Leadership is more about listening than talking
In my first year, I thought my staff needed to hear how much I knew. I filled meetings with solutions and answers. But I quickly realized that people didn’t need me to talk more; they needed me to listen better.
One afternoon, a teacher stopped me in the hallway. Instead of jumping in with my perspective, I just asked, “Tell me what you’re experiencing.” That five-minute conversation gave me more insight than a two-hour meeting.
Lesson: People won’t always remember your words, but they will remember if they feel heard. Leadership begins with listening.
2. Relationships build results
It’s tempting to focus on programs, test scores and initiatives right away. I did. However, the truth is that no initiative takes root without strong relationships.
Some of my most effective leadership moments weren’t in staff meetings; they were in the cafeteria line, standing outside at dismissal or writing a quick thank-you note to a teacher who went above and beyond. Those small, intentional gestures build the trust that makes big change possible.
Lesson: Relationships aren’t just “nice to have;” they’re the foundation of results.
3. The job will stretch you, protect your balance
I wish someone had told me earlier that the job would never be “done.” There’s always another email, another decision, another fire to put out. For years, I let the job consume me. I thought exhaustion was proof of commitment.
But I learned the hard way that leadership is a marathon, not a sprint. When I started protecting my time, leaving the building at a reasonable hour, setting aside me-time, even just taking a walk at lunch, I became a better leader.
Lesson: Your staff is watching how you model balance. Show them it’s possible to lead and still have a life.
4. Conflict is part of the job, don’t avoid it
Early in my career, I dreaded conflict. I thought it meant I wasn’t doing my job well. So I avoided it. But conflict doesn’t disappear; it grows.
I recall a situation between two staff members that I sidestepped, hoping it would resolve itself. It didn’t. By the time I stepped in, trust had eroded and the resolution was harder than it needed to be.
Lesson: Conflict is inevitable. Address it quickly, with empathy and clarity. Your role isn’t to eliminate conflict but to manage it with fairness and courage.
5. Vision without action is just a poster on the wall
As a new administrator, I loved sharing vision statements. Inspiring quotes. Motivational posters. But the truth? A vision without systems and accountability fades fast.
One year, I rolled out an exciting literacy initiative with energy and optimism. But because I hadn’t built a structure for follow-up, it fizzled. I learned to anchor vision in real steps: professional development, clear timelines, measurable goals. That’s how vision becomes reality.
Lesson: Dream big, but back it up with action.
6. Mentorship isn’t optional—it’s essential
When I first started, I thought I had to figure it out on my own. Asking for help felt like weakness. However, the turning point in my career came when I sought out mentors, leaders who had walked this road and could guide me.
And just as importantly, I learned the joy of mentoring others. Some of my proudest moments now aren’t about my own accomplishments; they’re about watching leaders I mentored step into their own roles with confidence.
Lesson: Asking for guidance isn’t a weakness, it’s a strength. Leadership thrives when we both learn from each other and lift others up when they need it.
7. You’re going to make mistakes, own them and learn
Here’s the truth: you will mess up. I certainly did. I mishandled meetings. I made assumptions. I pushed an initiative too quickly. I failed to communicate clearly.
What I’ve learned is that people don’t expect perfection—they expect honesty. When you own your mistakes, apologize and learn from them, you build credibility. You also model for your staff and students what real learning looks like.
Lesson: Perfection isn’t the goal. Progress is.
Growing through it all
Being a school administrator is one of the most challenging and rewarding roles in education. You will shape culture, support teachers and impact students in ways you may never fully see. But remember, you don’t need to have it all figured out today.
Leadership isn’t about knowing it all. It’s about growing through it all.
So, take a breath. Trust yourself. Learn from the handbook, yes—but lean into the lessons only experience can teach. And welcome to the work that will change you—and change lives—for the better.
