Leaders have an important role in initiating and shaping the democratization process. Formal and informal structures within the political system constrain possible options requiring leaders to exercise agency to manage expectations and facilitate change. This article examines the actions of F.W. de Klerk (South Africa) and Roh Tae Woo (South Korea) in initiating processes that eventually led to the consolidation of democratic political systems. The aims of the article are: (1) to identify the array of opportunities and threats faced by the two leaders; and (2) to determine the effect of regime form in shaping these structural factors. Drawing on previous work on the role of leadership in democratization, the analysis focuses on four factors: authority, institutions, opposition and continuity. To assess decisions made in the distinct political contexts the article examines how the respective structural configuration (one-party and military) was managed.