From Assistant Counselor to Aspiring Head: A Leadership Journey

From a young age, I witnessed the profound influence a dedicated educator and administrator can have on a child’s life. My mother was not only my first teacher but also an incredible educator who left a mark on the lives of many. She was a mentor, an advocate, and a guiding light for every student who crossed her path. Her tireless commitment to each child’s growth, academically and personally, inspired me to pursue a career in education and, eventually, leadership.

Growing up, I watched as my mother took on each new challenge with grace, resilience, and an unwavering belief in the potential of her students. Born to parents from Benton County, Mississippi who didn’t have more than an eighth-grade education, my mother’s ability to navigate academic spaces was astounding. She was the first of her three siblings to attend college, and even went on to receive her doctorate degree when she was 27. 

Years later, she became a single mother who emphasized the importance of accountability, responsibility, servitude, and kindness. She reminded me daily that I could do and become anything I dreamed if I was willing to work hard enough. And she taught me that education is more than teaching content—it is about cultivating confidence, curiosity, and compassion in others. This became the foundation of my leadership philosophy.

Finding My Footing 

If I count my years as a Girl Scout, captain of the basketball team, and student government secretary, it would seem like I’ve always been on a path to becoming a leader. But the experience that had the most impact on my leadership development was during the summer following my senior year of high school when I was offered an assistant counselor position with the National Youth Sports Program (NYSP) at Alabama A&M University, a historically Black college and university in Huntsville. I was told that I would be responsible for helping a lead counselor guide and support and 10-year-old girls. It appeared to be the perfect opportunity––until I realized there were only 1.7 adults trying to keep up with 50 girls. But what initially seemed like a disaster waiting to happen completely opened my eyes to the leader within me.

I learned new things about myself while supporting these girls. From learning to listen to their ideas to choreographing dance routines, I was building relationships with them. They began to trust me, and I realized that I enjoyed leading and learning alongside them. I affectionately became known as Ms. K.K., the counselor who knows all her campers’ names and who the girls adore. This experience transformed my confidence and taught me about the importance of being authentic, how to balance authority and approachability, and how I could impact the lives of others.

Refining My Skills 

When my career as an educator began in a first-grade classroom, I discovered the joy of helping students find their own voices. As I grew professionally, I realized my passion for education extended beyond my individual classroom to the idea of having a broader impact by supporting teachers and guiding schoolwide initiatives. 

Since then, I have served as director of admission and financial aid, division head, assistant division head, assistant director of auxiliary programming, and diversity, equity, and inclusion coordinator. And each of these opportunities has refined my leadership experience and skills in profound ways. Today, as the associate head of school and interim middle school principal, I’m helping to shape the academic culture of my school by empowering academic leaders, promoting collaboration, maintaining high academic standards, and creating a culture of trust and mutual respect. My support ensures that leadership is distributed across the school, collaborating with a strong network of individuals dedicated to fostering student success, teacher excellence, and alignment with our school's mission and values.

Empowerment is at the core of what I do every day as a leader. I believe in helping others recognize their strengths and providing them with the tools and support they need to flourish. I prioritize visibility, communication, and collaboration, making it a point to be present in classrooms, at school events, and in conversations with students, faculty, staff, families, and trustees. I encourage faculty to share their ideas, concerns, and successes, knowing that their voices are essential to our school's progress.

Aspiring to Headship

I am overjoyed to now be part of a special group of educational leaders, like my mother, who embrace the challenges and rewards of leading schools. This continues to fuel my desire to positively impact education––and to become a head of school, something I have aspired to since starting my independent school journey more than a decade ago.

Being part of NAIS’s Fellowship for Aspiring School Heads program has prompted me to think more deeply about headship. Since I became a fellow in April 2024, I have continued to refine my leadership abilities while preparing to take on the multifaceted responsibilities of leading a school. The program’s supportive and practical pathway to headship, which combines personal growth, professional development, and strategic insight, has been instrumental––the mentorship and peer collaboration in particular. Mentors are knowledgeable, dynamic, and optimistic about our cohort’s possibilities for headship, and every session is carefully constructed to encourage us as thinkers and problem-solvers who are reflective of our current practices and future responsibilities.  Through workshops, interactive discussions, case studies, and real-world scenarios, we explore approaches to navigating school culture and community and receive helpful feedback.

My journey in educational leadership continues to be shaped by my mother’s influence. When my mother retired from education, she retired as chancellor of a university. Although I was excited for her, I realized that the academic world was losing one of the best educators and leaders to have done this work. She instilled in me the belief that great leaders lift others up, and it is a lesson I carry with me every day.

Author
Kenyetta Wynn

Kenyetta Wynn, EdD, is the associate head of school, while also serving as the interim middle school principal at Holy Innocents' Episcopal School in Atlanta, Georgia.