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We investigated contextual organizational ambidexterity, defined as the capacity to simultaneously achieve alignment and adaptability at a business-unit level. Building on the leadership and organization context literatures, we argue that a context characterized by a combination of stretch, discipline, support, and trust facilitates contextual ambidexterity. Further, ambidexterity mediates the relationship between these contextual features and performance. Data collected from 4,195 individuals in 41 business units supported our hypotheses. A recurring theme in a variety of organizational literatures is that successful organizations in a dynamic environment are ambidextrous—aligned and efficient in their management of today’s business demands, while also adaptive enough to changes in the environment that they will still be around tomorrow (Duncan, 1976; Tushman & O’Reilly, 1996). The simple idea behind the value of ambidexterity is that the demands on an organization in its task environment are always to some degree in conflict (for instance, investment in current versus future projects, differentiation versus low-cost production), so there are always trade-offs to be made. Although these trade-offs can never entirely be eliminated, the most successful organizations reconcile them to a large degree, and in so doing enhance their long-term competitiveness. Authors have typically viewed ambidexterity in structural terms. According to Duncan (1976), who first used the term, organizations manage trade-offs between conflicting demands by putting in place “dual structures,” so that certain business units—or groups within business units—focus on alignment, while others focus on adaptation (Duncan, 1976).