Purpose: Historically, serving in the position of Assistant Principal has been thought to be an adequate training experience that prepares these administrators for school leadership. However, due to role ambiguity and limited professional development specifically focused on their needs, this group of leaders may lack the necessary abilities and sensibilities to meet the needs of a more diverse student population. The purpose of this study explores whether the roles, responsibilities, and professional development opportunities afforded to assistant principals have prepared them for leadership in diverse schools. Furthermore, this study explored assistant principals’ perceptions of their preparedness through the lens of culturally responsive school leadership. Research Methods: Following a qualitative case study design, this dissertation focused on the construct of culturally responsive school leadership theory. Six assistant principals, one school principal, and one district leader served as the participants for this research. Data were gleaned from interviews, document review, and researcher field notes. This study provides insight into the perceptions of preparedness of assistant principals to lead in diverse contexts and identifies professional development needs and some salient practices of culturally responsive school leaders. Data analysis followed the three-phase method defined by Strauss and Corbin (1994). Findings: Results indicated that the roles, responsibilities, and professional development provided to assistant principals have not fully prepared them for leadership in diverse schools. These findings also indicated a belief that lived experiences have helped with assistant principals’ preparation. Implications: This study illuminates the importance of providing assistant principals with ongoing, targeted professional development to meet their specific needs while providing some salient practices through the utilization of the Culturally Responsive School Leadership framework at the university, school district, and local school levels.