As superintendents steer their districts through uncharted territories, their experiences and strategies are key to transforming schools. This study employed transcendental phenomenology to explore how seven Virginia superintendents from two different regions described their experiences implementing novel cultural competency training. Data collection involved a semistructured interview protocol comprising six interview questions recorded and transcribed via Zoom. An open coding process was organized with NVivo 14 software to analyze participants' transcripts. The findings pointed to six interconnected themes, making it evident that implementing cultural competency training in educational settings involves multifaceted challenges and nuanced strategies ranging from political tensions and community engagement to recognizing cultural significance in education. The themes highlighted how transformational leadership aligns with the efforts required for successful implementation. The study's findings carry implications for leadership, addressing disparities, continued professional learning, and customized communication. Future research recommendations encompass replication on a larger scale; quantitative studies measuring the impact of cultural competency training or differences in experiences related to race, gender, or location; a longitudinal exploration of changes and trends over time; and an investigation into the direct influence of superintendents' leadership styles on successful implementation of cultural competency. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]