In one of his most cited works, March (1991) observed that “The basic problem confronting an organization is to engage in sufficient exploitation to ensure its current viability and, at the same time, devote enough energy to exploration to exploration to ensure its future viability” (p. 105). The need to simultaneously pursue exploration and exploitation is a cornerstone of organizational ambidexterity, with the embedded assumption that exploratory ventures require organic management systems and exploitative activities benefit from more mechanistic management systems. The authors argue that this assumption about system alignment is neither well-supported by empirical evidence nor well-grounded in March’s original ideas about exploration and exploitation. The authors review the existing empirical evidence on the management systems that support exploration and exploitation and reveal some of the empirical and conceptual challenges. The authors then share a quasi-experimental study of 49 project teams over an 18-month period where they investigated how components of the management system – formalization, specialization, hierarchy, and leadership – differentially affect project success for explore and exploit projects. The authors find that exploitation projects can succeed under either mechanistic or organic systems, but that exploratory project performance suffers under a mechanistic system. In addition, the authors also find that leadership is the most important determinant of project success or failure. The authors discuss the implications of these results for future studies of organizational ambidexterity and draw attention to some of the underdeveloped ideas in March’s original article that might further advance the field.