Over the years, many models of leader emergence and performance have been proposed. The Charismatic, Ideological, and Pragmatic (CIP) model of leadership attempts to account for the behavior of outstanding, historically notable, leaders. This model is based on three key propositions. First, the ways outstanding leaders make sense of their world determines their behavior. Second, differences in cognitive styles give rise to different forms of sensemaking. Third, three key styles, charismatic, ideological, and pragmatic, emerge in leaders’ sensemaking. In the present effort, we examine the intellectual origins of this model. We then consider some of the initial research providing evidence supporting the validity of this model. Finally, we examine some potential directions for future research.