Increased attention to improving a culture of belonging in clinical learning environments has led to various approaches to addressing microaggressions. However, most approaches in the literature focus on responding or reacting to microaggressions with insufficient attention to building trust before microaggressions might occur. Research on microaggressions in clinical learning environments suggests anticipatory or pre-emptive conversations about microaggressions may foster greater trust. In this study, the authors explored how diverse participants perceived the experience of anticipatory conversations about potential microaggressions. Overall, the authors sought to gain a deeper understanding of how pre-emptive and anticipatory conversations may influence an organization's approach to addressing microaggressions in clinical learning environments. The authors utilized constructivist grounded theory methodology and conducted individual qualitative interviews with 21 participants in an academic department within a larger health sciences center in the United States. Findings suggest that anticipatory conversations about microaggressions were challenging due to existing norms in dynamic clinical learning and working environments. Participants shared that the idea of anticipating microaggressions elicited dissonance. Conversations about microaggressions could potentially be facilitated through leaders who role model vulnerability, organizational supports, and an individualized approach for each team member and their role within a complex hierarchical organization. Anticipating and addressing microaggressions in clinical learning environments holds tremendous potential, however, any conversations about personal identity remain challenging in medical and healthcare environments. This study suggests that any attempts to address microaggressions requires attention to cultural norms within healthcare environments and the ways that hierarchical organizations can constrain individual agency.