Despite the uptick in awareness of racial and other sociocultural diversity owing to recent social movements particularly in the United States but also in many countries in Europe, deep understanding of identity and bias is lacking and remedies for policy and practice inequities in the education sector remain. Steadily increasing racial and linguistic heterogeneity demands better understanding on the part of school leaders—and the larger school staff—to redress inequity and improve schooling for all students. This study utilized in-depth interviews to gather secondary school leaders’ perspectives on, and level of engagement with, diversity in Fribourg, Switzerland. Findings revealed that school leaders are, overall, inadequately prepared to tackle difficult, identity-charged conversations or to confront their own positionality and subjectivity vis-à-vis newcomer students. Recommendations are made for aspiring and current school leaders to become active by practicing diversity-engaged leadership.