The development and enactment of leadership involves paradoxical tensions. Cultural and organizational forces increasingly reflect an awareness of paradox. Leadership is correspondingly understood as having paradoxical aspects. I address the relationship between leadership and paradox and explore the utility of the competing values framework as a means to develop leadership skill from a paradox perspective. The competing values framework can support the development of a more paradoxical view of leadership that encourages greater leader behavioral and cognitive complexity as well as increased leader flexibility. Furthermore, the capacities of awareness, exploration, and interpretation are identified as possible resources to advance paradoxical conceptualizations of leadership.