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Applying the analytic lens of critical whiteness, we examine the relationship between leader-initiated discussion norms and the quality of racial dialogue in educator professional development. We draw on data from a five-session virtual “antiracist book study” in a rapidly diversifying U.S. district, convened and facilitated by a district administrator. Observed discussions tended toward the superficial and did little to challenge participants’ existing worldviews. We argue that the district leader’s facilitation moves and his selective enforcement of norms were shaped by his centering of participants’ “safety” over their learning, which together reinforced persistent manifestations of Whiteness. We offer implications for the facilitation of antiracist professional learning and for system-wide leadership on equity.