Minoritized students in public schools in Texas and across the nation continue to underachieve academically compared to their white peers. Despite similar academic achievement and socioeconomic backgrounds, minoritized students are often perceived more negatively by a predominantly white teacher workforce. The idea of cultural dissonance or mismatch between teachers and their students has led to the development of pedagogical frameworks such as culturally responsive teaching (CRT) that seek to bridge this cultural gap. This embedded multiple case study examined the perceptions, lived experiences, and level of preparedness of four school principals and one assistant superintendent in a white-majority school district with rapidly changing demographics. My findings support previous studies that show the limited resources and continued failure of universities and school systems in building educator capacity in culturally responsive school leadership CRSL. Furthermore, culturally responsive and visionary leaders may be more critical than previously thought due to school systems imbued with the dominant white culture and its deeply ingrained stereotypical views towards minoritized individuals. Despite these findings, my study also provides compelling evidence that meaningful relationships and diverse experiences alone can play an important role in fomenting and enhancing individuals' cultural proficiency, regardless of their racial/ethnic background. Finally, the implications of these findings are discussed in detail, followed by recommendations.