Would I Want to Be a Learner in My Leadership?

It was the second day of school, and I had just asked my students to write about their first-day experience at our high school. Their responses stunned me. Over and over, they described the day as boring, repetitive, and impersonal. Every class felt the same: assigned seats, syllabus read-alouds, textbook distribution, maybe a pre-test if the teacher was feeling adventurous.

That wasn’t what I wanted my classroom to feel like.

And yet, there it was in their writing, clear and undeniable. I had contributed to the very experience I wanted to avoid. I had fallen into the rhythm of routine, even though I knew better. When I was teaching French, I went out of my way to hook my students on day one. I made sure they spoke French before the bell even rang. But after shifting to English, I had slowly, quietly, become part of the “monotony machine.”

That realization led me to one of the most powerful leadership reflections I still carry with me: Would I want to be a learner in my own environment?

It’s a question that transcends the classroom.

First Impressions Stick: What Tone Are You Setting?

Whether it’s the first day of school or the first meeting with a new team, the tone we set at the beginning matters. As leaders, we are always communicating something through our agenda, our demeanor, even the layout of the room. Are we signaling collaboration or compliance? Energy or exhaustion?

That first day, I decided to rewrite the script. I designed learning stations that reflected the values I cared about: humor, collaboration, technology, and relationships. My students were up and moving, laughing, problem-solving, and applying their summer reading in a meaningful way. Even the hiccups, like tech failures and time miscalculations, didn’t derail the energy. The message was clear: This class will be active. Your voice matters. Let’s learn together.

Leaders have the same opportunity. Every onboarding, every initiative kickoff, every coaching conversation is a chance to set the tone. Is your leadership signaling curiosity, respect, and purpose?

Listening to Feedback Builds Trust

My shift didn’t start with a great idea; it started with listening. Had I not asked students to reflect on their experience, I might never have known how disengaged they felt. And more importantly, they wouldn’t have known I cared enough to ask.

Leadership requires courage to invite honest feedback and humility to act on it.

Too often, leaders assume silence means satisfaction. But we don’t build trust through assumption. We build it by creating safe spaces for input, then following through with change. That’s true whether we’re mentoring a new teacher, coaching a tech team, or building a district-wide vision.

Trust grows when people know their voices matter.

Self-Reflection Is a Leadership Superpower

One of the most valuable habits I learned as a teacher and now practice as a district leader is honest reflection. Not just “what went wrong” but “what do I value enough to change?” That question reframed everything for me.

When I asked myself, “Would I be excited to sit in my own class?” the answer wasn’t a proud yes. And that was hard to admit. But real growth starts with asking hard questions and being willing to face the answers.

In leadership, it’s easy to default to what’s familiar. But transformative leaders carve out time to pause, assess, and recalibrate. They challenge their own assumptions. They model growth.

Reflection isn’t about guilt; it’s about alignment.

Start with Why, Then Design for How

After reading my students’ reflections, I realized I had let the “how” of the first day (textbooks, rules, rosters) take priority over the why (building culture, sparking curiosity, valuing learners).

When I redesigned the first day, I started with why I teach: because I believe in the power of learning to change lives. Then I designed experiences to show students what that could look like. Humor through a John Green video. Tech integration through a virtual board of selfie introductions. Collaboration through their creation of a syllabus scavenger hunt we did together on Day 2.

Leaders, too, need to start with purpose. Why are we launching this initiative? Why does this process matter? When the why is clear, the how can be flexible. That’s how we design people-first cultures, not with mandates, but with meaning.

Celebrate Progress, Not Perfection

That first station-based day wasn’t flawless. One group didn’t finish. Another had to swap digital tools for sticky notes when the internet went down. I ended up doing a three-minute impromptu mini-lesson on plot structure.

But here’s what mattered: students were engaged. They were curious. They wanted more.

In leadership, we often delay innovation until the plan is airtight. But momentum doesn’t come from perfection. It comes from progress.

Celebrate what’s working. Share what you’re learning. Invite others into the process. That’s how culture shifts.

From the Classroom to the Boardroom

The first-day story may be rooted in my time as a classroom teacher, but the lessons have never stopped applying. I still ask myself, Would I want to be a learner in this meeting? This retreat? This change process?

Today, that question shapes how I:

Design my interview process for new team members

Facilitate team sharing and learning

Mentor emerging leaders

Present at conferences

Coach edtech partners

The environments we create as teachers, as mentors, and as leaders are always sending messages. Let’s make sure we’re sending the right ones.

Let’s lead in ways that welcome curiosity, celebrate individuality, and center the human experience.

Because if we wouldn’t want to be a learner in our own leadership, it’s time to change the lesson plan.

Design for the experience you’d want to have. Start with empathy, build with purpose, and reflect often. You don’t need perfection to lead well. You just need intention.