This cross-case case study explores how two White principals took the first steps to engage in racial conversations. Using the constructs of race consciousness and antiracism, race neutrality, and resistance to racial dialogue to frame our findings, we illustrate how both principals broached the topic of race with staff members. We demonstrate how the structures of whiteness hindered the principals' progress toward addressing systemic racial inequities within their respective schools. Our article concludes with recommendations and strategies for principal preparation programs and practicing school leaders.