The student population in the United States is growing in diversity (Frankenburg & Lee, 2002; Orfield & Lee, 2004; Tefara, Frankenberg, Siegel-Hawley, & Chirichigno, 2011), challenging school leaders to develop or fine-tune their cultural competence in order to meet the needs of the changing student population (Bustamante, Nelson, & Onwuegbuzie, 2009). As a result, expanding knowledge of cultural competence is necessary for school leaders as a way to meet state and federal requirements for student subgroups and to meet new credentialing standards for school leaders (ISLLC 2015 Standards Draft Version; Oregon Department of Education Summit on Cultural Competence, 2004; VA Guidelines for Uniform Performance Standards and Evaluation Criteria for Teachers, 2011). This is especially important for assistant principals who must navigate the new terrain of school leadership while working to understand students who may not come from the same cultural background (Madhlango & Gordon, 2012). Through a descriptive case study (Merriam, 1998), this project examines the experiences of two assistant principals, one from an elementary school and one from a high school, who worked as part of a leadership team that increased academic achievement in their diverse schools. The study addresses the following question: How do school assistant principals working at a school with a demonstrated record of success in student achievement, lead schools in culturally competent ways through intentional and enhanced relationships with students? The primary case unit of analysis is the assistant principals, but interviews with teachers and principals provide further confirmation to support the evidence from the assistant principals. Findings indicate that assistant principals can have a positive impact through discipline and community actions. Assistant principals acknowledge that mentors who are deliberate in their work in schools with students of poverty combined with their own personal experiences as teachers is crucial to the decisions they make when interacting with students and their families.