Purpose: We investigated the way in which structured, multiyear conversations about race and institutional racism occurred in suburban secondary schools with changing racial demographics. Research Framework: The study draws on interpretive research traditions, in that we assume that how teachers understand race and racism will influence how they work with colleagues and students. As such, the research examines to what extent talking about race and learning about institutional racism affects educators' mental models and their classroom practices. Method: Secondary schools in three districts that had participated in ongoing professional development related to racial equity were selected. Grounded theory methods were used for data collection, coding, and analysis of interviews with teachers and administrators. Findings: This study revealed that principal leadership affected teachers' engagement in this work. When this occurred, teachers made meaningful changes in classroom practices and their school communities. The primary findings of the study are: (1) fear of being considered racist was a barrier for White teachers and administrators that impeded collective focus on racial achievement gaps; and (2) principals' deep personal engagement over a period of several years encouraged a process of confronting and mitigating this fear, and helped teachers engage with the implications of race for school and classroom practices. Significance: Discomfort, a critical element in confronting racial inequities in schools, requires school leaders, particularly principals, to authentically participate and engage in order to foster teacher change.