From Leonardtown To The National Stage: Principal Deborah Dennie Reflects On Leadership And Impact

LEONARDTOWN, Md. — At Leonardtown Middle School, Dr. Deborah Dennie’s leadership is felt long before it’s formally seen.

From the moment students walk through the doors, there’s a rhythm to the building, one shaped by connection, consistency and trust. During class changes, Dennie is a familiar presence in the hallways, greeting students with high-fives, fist bumps and quick check-ins that reflect the culture she has spent a decade building.

That culture — one rooted in relationships — recently placed her among the top three middle school principals in the nation.

“I don’t think I’ve ever had that feeling before,” Dennie said in an interview with The BayNet, recalling the moment she learned she was a finalist for the National Principal of the Year Award. “I was shaken. I had sweaty palms. It was like — did he just say that? I’m a finalist?”

From Leonardtown To The National Stage

Dennie, who has led Leonardtown Middle School for 10 years, was selected as Maryland’s Middle School Principal of the Year before advancing to the national level through the National Association of Secondary School Principals.

Her journey culminated in a three-day experience in Washington, D.C., where the National Education Leadership Awards Gala served as the final event — but far from the only focus.

“When I saw the agenda, I thought, are we really doing something every hour on the hour?” Dennie said. “But it was awesome. These were truly things you can bring back to your schools or your districts.”

More Than A Gala: Learning, Collaboration And Problem Solving

Rather than a single-night celebration, the national event was designed as an immersive leadership experience, bringing together principals, assistant principals and student leaders from across the country.

Over the course of several days, participants engaged in workshops, roundtable discussions and interactive sessions focused on strengthening leadership practices and tackling real-world challenges in education.

“We had to come up with a problem, narrow it down, and then really ask: how do we know this is a problem?” Dennie said. “Who is affected? What’s within our control to change? What would success look like?”

The structured problem-solving approach, she said, offered valuable tools she plans to bring back to Leonardtown Middle School.

Another standout experience was a “fishbowl” discussion format, where students, assistant principals and principals each took turns sharing perspectives, reinforcing the importance of listening across all levels of a school community.

“It was a learning experience,” Dennie said. “It wasn’t just about being recognized, it was about growing.”

A Leader Built On Trust And Teamwork

While Dennie’s recognition highlights her leadership, she is quick to emphasize that the success of Leonardtown Middle School is deeply shared.

“I could not have done this by myself,” she said. “I am standing on the shoulders of my staff.”

She describes her staff as her “LMS family,” a team that not only supports her vision, but actively helps bring it to life.

From implementing new initiatives to embracing creative ideas, Dennie credits her teachers with being open, adaptable and deeply committed to student success.

“They put up with all my ideas,” she said with a laugh, pointing to programs and initiatives that rely heavily on collaboration and trust.

But beyond programs and planning, it’s the daily partnership that defines her leadership.

Dennie works closely with teachers to monitor student progress, identify gaps and create targeted support systems. She also meets directly with students who are struggling, often taking time out of her schedule to help them get back on track.

“It’s all about the kids,” she said.

A Culture That Starts With Adults

Dennie believes that strong student outcomes begin with strong adult relationships, and she works to foster an environment where teachers feel supported, heard and empowered.

Collaborative planning, open communication and mutual respect are central to that culture. Whether it’s problem-solving challenges, celebrating successes or navigating difficult situations, Dennie emphasizes working together as a unified team.

That trust allows teachers to take risks, try new approaches and invest more deeply in their students — knowing they have the backing of their principal.

In turn, that connection filters directly to the students.

“I call them my LMS family,” Dennie said, describing the relationships she has built with her staff.

Bringing It Back To Leonardtown

While the national recognition is significant, Dennie remains focused on what matters most: her students and her school community.

Many of the strategies and ideas she gained from the national experience, particularly around collaboration and problem-solving, are already being applied within her school.

From attendance initiatives and student engagement efforts to ongoing staff collaboration, Dennie continues to refine and strengthen the systems that support student success.

“I try to incentivize everything,” she said, describing creative approaches that help keep students motivated and engaged.

Those incentives range from schoolwide initiatives to smaller, student-centered efforts. One of the school’s most popular events is an annual classic car show — a community-driven reward tied to positive behavior and discipline goals, where students help organize, judge and participate in the event.

Dennie has also introduced creative attendance campaigns, including peer-to-peer outreach where students are encouraged to check in on classmates who are absent and motivate them to return to school.

Other efforts include themed competitions, student recognition opportunities and interactive activities like grade-level challenges and staff-versus-student events, all designed to build engagement while reinforcing expectations.

Each initiative, she said, serves a larger purpose.

Those efforts continue to evolve, with Dennie sharing weekly updates and school highlights through her newsletter, offering an inside look at Leonardtown Middle School.

Rooted In Purpose

Long before the awards and recognition, Dennie knew she wanted to be in education.

Growing up, she set her sights on becoming a teacher, a goal that began taking shape earlier than most. After graduating high school at just 16, she entered the workforce while waiting for an opportunity to step into the classroom.

“I always wanted to be a teacher,” she said.

At one point, her path nearly shifted. With encouragement from her family, Dennie secured an interview to pursue a career in nursing — a stable and respected profession. But when the moment came, she realized it wasn’t where her passion lived.

“I told my mom, ‘I can’t do it. That’s just not me,’” she said.

Instead of taking a different route, she chose to wait, holding onto her goal of becoming an educator. Within a year, that patience paid off.

Dennie began teaching at 17 years old, stepping into a classroom of students just two years younger than she was.

From there, her journey in education only grew — from the classroom to assistant principal, and eventually to leading an entire school community.

While her role has expanded over the years, her purpose has remained the same.

“I’m at peace when I work,” she said. “This is all I’ve ever wanted to do.”

Today, that early passion continues to shape her leadership, guiding the way she connects with students, supporting her staff and building a school environment where every child has the opportunity to succeed.

A walkthrough video of Leonardtown Middle School captures Dr. Deborah Dennie in action — greeting students in the hallways and interacting with her school community, reflecting the relationship-driven leadership style that earned her national recognition.

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