This research departs from the actualization of the kiai's leadership role in santri character education in Islamic boarding schools, which consists of the role of goal rationality, spirituality, and interpretation of the vision of education in Islamic boarding schools. This research aims to describe the role of the kiai in forming the character of santri in the Asy-Syifa Islamic boarding school. This research used a qualitative approach with descriptive methods. data collection with interviews, observation and documentation studies, also data analysis and valid data testing. the results of research on how kiai act as pathfinding, a lightning and empowering in the process of forming the character of santri, this is illustrated by how the kiai synergizes the great vision of kiai and Islmic boarding school, with typical learning and Islamic boarding school culture and relational patterns of kiai-santri, santri-kiai and santri-community as a comprehensive process of character education patterns in the Asy-Syifa Islamic boarding school