My purpose here is to join the scholarly conversation (Huff, 1999) concerning the development of managers (Detrick, 2002; Donaldson, 2002; Pfeffer & Fong, 2002) and to introduce the reader to two similar constructs developed in differing paradigms: sensemaking and learning. Through a review of the characteristics of sensemaking and the conceptual orientations to adult learning, similarities and contradictions emerge. Both constructs deal with the creation of meaning, the necessity for action to be linked with cognition, and the importance of both subjective and objective knowledge. Differences appear with respect to the role of critical reflection and the impact of social structuring on meaning making. Although contradictions emerge, after examining each construct independent of the other, I suggest that the two constructs are actually complementary. To identify this symbiotic relationship, I offer two implications concerning the conceptualization of managerial work and the development of managers.