Every Early Career Principal Deserves a Mentor

How one CCOSA director learned to provide specific, intentional support.

By Chris LeGrande, OASSP/OMLEA Executive Director

Over the past nine months, I had the opportunity to complete the National Mentor Training and Certification Program offered by the National Association of Elementary School Principals (NAESP). As Executive Director of OASSP/OMLEA, a key part of my role is to support school leaders and provide training through CCOSA’s Principal Coaching and Mentoring initiative. To deepen my impact and refine my skill set, I enrolled in this comprehensive mentoring program – and came away with a renewed belief: Early career principals thrive when they have access to a strong, experienced mentor.

The Value of Intentional Mentorship

NAESP’s mentor program is grounded in three essential leadership pillars: Building Culture, Empowering People, and Optimizing Systems. These are paired with the Six Competencies of Effective Mentors, creating a robust framework designed to support site-level administrators in meaningful, practical ways.

For new principals, the demands of the job can feel overwhelming. Establishing a shared mission and vision, distributing leadership across the school, prioritizing student and staff growth, and practicing professional well-being – all while navigating daily crises – can quickly become a heavy burden. The emotional and physical toll is real. But an experienced mentor can provide clarity, encouragement, and strategies that help new leaders not just survive but thrive.

Culture First, Strategy Second

Strong principals understand the outsized impact school culture has on learning. I’ve often heard the phrase, “Culture eats strategy for breakfast,” and it holds true. Even the best-laid plans fall flat without a positive, values-driven culture.

During my mentoring experience, I found that many principals value the idea of shared beliefs and a unified mission but don’t always know how to bring those to life. Working with me, my mentee Ashley Mackey, a first-year principal at Deer Creek High School, launched a series of committee meetings that included teachers and staff from across the building. Through those conversations, we concluded that a SWOT analysis (Strengths, Weaknesses, Opportunities, Threats) would be helpful in identifying key values and co-creating a school vision. The result? A culture built not by edict, but by shared ownership.

For eleven years prior to joining the CCOSA team in July 2023, Chris LeGrande served as Principal at Guthrie High School, home of the Bluejays.

Trust: The Cornerstone of Mentorship

One of the most powerful aspects of effective mentorship is the creation of a safe, confidential space for honest dialogue.

NAESP’s Competency Four highlights that effective mentors should cultivate a trusting environment that encourages open and reflective conversations. We were discouraged from serving as mentors to individuals we directly supervise or evaluate. Doing so hinders trust and vulnerability – two qualities essential to authentic growth.

Because I was not in a supervisory role, Ashley felt free to share candidly. She could express uncertainty, admit mistakes, and discuss challenges without fear of judgment. That trust laid the groundwork for deep reflection and rich, solution-oriented conversations – something every new leader needs.

Ask More, Advise Less

Another lesson I learned: Effective mentors ask more questions and give less advice. As school leaders, we’re conditioned to solve problems. But in a mentoring relationship, the goal is empowerment, not direction.

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• career principals need more than training –they need a trusted guide, a sounding board, and a source of encouragement.”

Rather than jumping in with solutions, I practiced the art of inquiry, asking thoughtful, reflective questions like, “What have you tried?” or “Have you considered…?” This helped Ashley think critically and take ownership of her decisions. It also reinforced that she already possessed the knowledge and instincts – she simply needed space to process.

Mentorship Is a Two-Way Street

Perhaps the most unexpected benefit of my mentoring journey was the mutual growth that took place. Though I was confident in my ability to support a first-year principal, I was initially unsure about mentoring someone leading a school twice the size of any I had ever managed. What I discovered was that school size doesn’t change the fundamentals of leadership. In fact, the experience reaffirmed just how universal our challenges are. I learned just as much from Ashley as she did from me – lessons about work-life balance, focusing on what truly matters, and not letting isolated setbacks overshadow the good.

A Collective Responsibility

Let’s face it: Being a principal is one of the toughest roles in education. It’s demanding, isolating, and emotionally taxing. And as the teacher pipeline shrinks, the pool of aspiring administrators is growing shallower still.

If we want to cultivate strong, resilient school leaders, we must make mentorship a priority. Early career principals need more than training – they need a trusted guide, a sounding board, and a source of encouragement. My experience has made one thing clear: Principal development, sustainability, and long-term success all begin with intentional, compassionate mentorship.

If we truly believe in growing futureready leaders, it’s time we commit to walking beside them – one conversation, one question, and one shared moment at a time. ■

CCOSA’s Principal Coaching: Supporting & Sustaining School Leaders is designed for veteran principals who mentor other principals or for superintendents or central office administrators who mentor and supervise building leaders. The next cohort will meet three times during the fall 2025 semester. Click here to register.