While common philosophical foundations influence instruction and leadership in East Asian nations, variable historical factors also significantly impact education within these countries. The current study was designed to holistically examine educational systems in different Confucian contexts, so that contemporary issues and necessary reforms may be identified. Aspects of leadership, organizational responsibilities, and educational challenges were analyzed using the Program for International Student Assessment (PISA). Results suggest that new types of leadership are needed to empower administrators and teachers in East Asian countries. Such reforms cannot become successful, however, unless innovative techniques are developed which adapt Western theories to the highly defined status hierarchies of Confucian societies.