Advice I Wish I Had Heard Before Becoming a School Administrator

I’ve been fortunate to experience what many would consider a successful career. I’ve served as a superintendent in two districts, been named Illinois State Superintendent of the Year, published books, given keynotes nationally, and led award-winning school improvement efforts. But I say this with complete honesty: Nothing was more difficult than my first year as a principal.

That year was harder than my divorce, the foreclosure of my house, or battling cancer three times. It was the loneliest, most mentally and emotionally taxing year of my life. I struggled so much that there was a full-on student and staff walkout in protest of me. That experience left a mark so deep that I chose to center my doctoral dissertation on the difficulty of the first-year of the principalship.

What I learned from that research—and from living it—is that success in leadership doesn’t come from title or talent alone. It comes from support, self-awareness, courage, and clarity. Below are three lessons I wish someone had drilled into me before I ever sat in the principal’s chair—along with practical steps you can take this summer.

Invest in Coaching

If your district doesn’t provide it, find it yourself. There’s no faster way to accelerate your growth than through regular, structured coaching. Not mentorship—coaching.

Mentors are often assigned. They’re often kind, supportive, and available. Coaches are different—they’re intentional. They ask hard questions, help you focus, and hold you accountable. A coach doesn’t just support your leadership—they sharpen and accelerate it.

In my first year as a principal, I was awful. I thought leadership was about outworking everyone and designing perfect policies. I showed up early, stayed late, pushed relentlessly—and got crushed. I micromanaged. I isolated myself. I tried to earn respect by proving I had all the answers. I honestly don’t think I would’ve recovered without coaching.

What changed me was someone finally having the courage to ask better questions. A coach helped me see that leadership isn’t about being the hardest worker or the smartest person in the room—it’s about moving human beings forward. That shift in mindset saved my career. It saved me. Without that, I would’ve flamed out completely. Probably fast.

Leadership feels heavy because it is heavy. But when you have the right support, it’s also deeply fulfilling.

Try this:

• Interview coaching options now. Ask about availability, cost, and values alignment.
• Set up biweekly sessions from August to December. That early accountability is a game-changer.

Be Authentic

In year one, you will hear about every single one of your leadership flaws—directly or indirectly. You’ll get feedback from staff, students, parents, and district leadership. Some of it will be fair. Some of it won’t. But all of it will feel personal. The danger is this: You’ll start trying to fix everything people say is wrong with you. You’ll lose yourself in the process.

That’s exactly what happened to me. Early on, I made the mistake of thinking I had to act like a principal. I studied how other leaders carried themselves and tried to emulate them—thinking if I looked the part, I could lead like them. It didn’t work. My staff saw through it. And worse, I lost clarity on who I was and what I stood for.

My superpower has always been my directness. I don’t sugarcoat things, and I believe that not working hard on behalf of kids is unacceptable. That kind of apathy offends my sensibilities. I had to learn how to temper my approach—how to listen better, how to deliver truth with more care—but I couldn’t turn that part of me off. It’s what got me into leadership in the first place. When I tried to mute it, I lost my edge, and worse—I lost my impact.

The turning point came when I stopped performing and started leading. I sat down and wrote my own leadership credo—my core beliefs, values, and nonnegotiables. That process gave me something solid to return to on hard days.

When you lead with authenticity, you communicate with more clarity, make faster decisions, and earn deeper trust. Your people don’t need a polished version of you. They need you—real, flawed, and committed.

Try this:

• Write your leadership credo. One page. What do you believe? What do you stand for?
• Ask five people to describe you in five words. Compare their answers with how you think you show up. What’s aligned? What’s not?

Don’t Delay Change in the Name of Relationships

This is the advice I heard most often—and the one I disagree with most: Spend your first year building relationships, then make changes in year two.

No. You were hired to lead—not to protect the status quo.

Let me be clear: You absolutely need to listen. You absolutely need to learn. But you also need to lead—and that means in year one. The motto here is simple and nonnegotiable: Listen. Learn. Then Lead. The problem is that too many new leaders get stuck in the first two. They delay tough decisions, and by the time they finally move forward, people feel blindsided—or worse, manipulated.

I’ve lived this. Early in my principalship, I thought I was being thoughtful by waiting to make changes. But when I finally did act, the response was harsher than it needed to be—not because the ideas were bad, but because the timing felt dishonest. People didn’t trust the delay. They thought I was hiding my intentions.

You don’t have to choose between relationships and results. The best leaders build trust by being honest, clear, and mission-driven. You can be kind and urgent at the same time.

Try this:

• Identify three core things that must change. Build your case: What’s broken? Why does it matter? What’s your plan?
• Use your first staff meetings to lay out what you value and what you expect—with warmth, clarity, and transparency.

Lead with conviction—and grace. Leadership isn’t about being perfect. It’s about showing up with clarity, courage, and a commitment to grow—every single day.