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Developing leader self-awareness is widely accepted as central to leader education and development, but leader development theory remains nascent. Our aim is to shift consensus among leader development scholars and practitioners to recognize the limitations of current approaches to developing leader self-awareness and the pressing need to develop more advanced leader self-awareness. The key limitations in extant approaches are a lack of consideration of external forces that shape self and a failure to account for “self” as an ill-structured problem—that is, a problem without a single correct answer. To address these limitations and guide the shifting of consensus, we theorize the function of reflective judgment in enabling more complex and holistic leader self-awareness by reflecting on how leaders’ formative places shape who they are and how they lead. We detail a place-based structured reflection …