What makes teachers stay in your school?

In this episode, Dr. Dennis Chapman shares the findings from his PhD dissertation, which explored teacher retention through the lens of servant leadership. Drawing on data from 2,000 independent school educators, Dennis reveals the seven leadership traits that matter most—and how school heads can lead with authenticity, trust, and purpose.

At The Village School of Naples, where Dennis serves as Head of School, this approach isn’t just academic—it’s real. The school achieved a 97% teacher retention rate last year, underscoring how powerful values-driven leadership can be in practice.

Whether you’re an aspiring leader or a seasoned head of school, this conversation will reshape how you think about faculty culture and retention.

What You'll Learn from Dr. Dennis Chapman:

Servant Leadership Matters – Teachers who feel seen, valued, and trusted by their head of school are significantly more likely to stay, regardless of compensation.
The “7 C’s” of Retention – Communication, Culture of Appreciation, Compassion, Connection, Cultivating Trust, Compensation, and Coaching the Admin Team emerged as consistent themes among satisfied faculty.
Compensation Is Not Always King – Teachers committed to their schools rated pay as less important, while those looking to leave ranked it highest.
Authenticity Over Performance – Leaders who “perform” appreciation or visibility without sincerity risk damaging trust rather than building it.
Early Feedback Prevents Surprises – Pulse surveys, transparent compensation models, and open conversations help reduce last-minute departures.

Discussion Prompts

Which of the “7 C’s” of servant leadership—Communication, Culture of Appreciation, Compassion, Connection, Cultivating Trust, Compensation, and Coaching the Admin Team—are we currently strong in, and which ones need more focus?
How does our current compensation structure support or hinder faculty retention?
In what ways are we showing appreciation to our teachers consistently? Are those efforts meaningful and authentic?
What systems do we have to gather honest faculty feedback, and how effectively are we acting on it?
How transparent are we with our communication around key decisions? Where could we be more open or inclusive?
How are we developing our division heads and admin team to embody servant leadership in their daily work?

Why Teachers Stay: Insights from 2,000 Independent School Educators

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