A school leader representation gap exists in the nation's public schools. There is an underrepresentation of public-school leaders of color, which results in inequity of cultural values and diverse leadership perspectives that impact recruitment, retention, and student success. Only 22% of school leaders identify as people of color, while 53% of students are non-White. This basic qualitative study focused on exploring the professional experiences of five African American school leaders, located in the Midwest, with a focus on the experiences prior to becoming a school leader and the current experiences as a school leader. Additionally, this research also explored how school leaders of color perceive their impact on Black students in their schools. Critical race theory and representative bureaucracy theory were both used as theoretical frameworks to deepen understanding around the school leader representation gap. Critical race theory helped frame the reasons for and the importance of closing this gap, considering the historical inequalities in the U. S. Representative bureaucracy theory framed the potential impact of representational leadership on students of color. The study was conducted utilizing one on one virtual interviews in a semi-structured format. An emergent open coding process, alongside three levels of analysis was conducted. Five themes emerged: sense of identity, pathways to becoming a school leader, keys to longevity, persistence in the face of obstacles, and the why. This research resulted in recommendations for principal preparation programs, school districts and policy makers looking for ways to develop more diversity in the school leader role. [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.]