In response to the demographic divide between administrators and students in urban public schools, this study examined the experiences of 5 White urban school leaders participating in an anti-racist reflective leadership group called WAKE UP! (White Administrators Addressing K-12 Equity by Unpacking Privilege). The administrators in this sample were committed to improving outcomes for students of color, citing numerous social justice initiatives that had been implemented across the organization. Action research methodology was used to develop the WAKE UP! program model based on participant feedback throughout the study. An embedded case study approach was used to examine the experiences of participants using two units of analysis—critical self-reflection and White racial identity development. One limitation of this study was that grouping the administrators into a (White-only) affinity group limited exposure to other perspectives. Once data were collected, I analyzed individual participant experiences and generated themes, or lessons learned, across the cases. Lessons learned from case study analysis indicated that the WAKE UP! program model was effective in prompting participants to question and reframe assumptions about the manifestation of racism in their schools, providing a venue for critical thought and analysis of racial and cultural differences. Through this process, participants began to identify their own implicit bias and to recognize that the affinity group aspect of this program created a safe space for discussing racism. As the result of participating in WAKE UP!, they identified the manifestation of societal and institutional racism in their schools and identified implicit bias as they unpacked their own White privilege. The group learned that engaging in critical self-reflection can be painful, but this tension is necessary for racial identity development. Racial identity development for White school leaders happens with intentional action, resulting in personal and professional changes. Lessons learned from the action research process suggest that the facilitator of an anti-racist reflective leadership group must be in the autonomy status described by Helms (1997) Model of White Racial Identity Development. In the autonomy status, a positive White racial identity is internalized and the facilitator models anti-racist behaviors, ongoing critical self-reflection, and increased effectiveness in multiracial settings.