This chapter focuses on the leadership styles of political executives—that is, the ways in which executives relate to constituents, advisers, and other leaders in the political domain. The scholarship on this topic, spanning the fields of political science, psychology, management science, and public administration, provides answers to fundamental questions about when leaders matter and which aspects of leadership style generate specific policy-making processes and outcomes. General conclusions include the dual importance of contextual factors and political skill in shaping leaders’ effectiveness, and the central roles played by leaders’ task versus relations orientations and sensitivity to the political context. Significant progress in this field will require more research on non-Western leaders, rigorous comparative analysis of political executives, methodological refinement in measuring leadership styles, ‘bridge-building’ among balkanized academic subfields, and more systematic efforts to identify areas of consensus and gaps within the existing scholarship.