This research is motivated by weak Islamic boarding school management, limited human resources, infrastructure and budget limitations, long study time and the increasingly unstoppable influence of external culture. The existence of Islamic boarding schools cannot be separated from the role of kiai as caregivers. In the context of Islamic boarding school leadership patterns, kiai have an important and strategic role in the development of Islamic boarding schools. The challenge then is how the kiai's leadership pattern can face the ongoing flow of change and educational development. How learning in Islamic boarding schools can improve its quality through kiai leadership patterns. This research generally aims to conduct an analysis of kiai leadership patterns in managing Islamic boarding school learning. The specific aim of this research is to obtain an explanation of the kiai's strategy in developing kholaf learning in Islamic boarding schools. Therefore, the theory used in this research is Weber's leadership theory and reconstructionism from George S. Counts. The method used in this research is qualitative descriptive analytic. Then the findings from this research are that kiai leadership with a complete personality attracts students in particular and members of the surrounding community. The students and community members hope for blessings, wisdom and
ma'unah from the kiai. The kiai's leadership in organizing and managing the Islamic boarding school shows responsibility and full attention, attracting and having a big influence on the students. The attitudes, behavior and actions of the kiai are observed, followed as examples and interpreted by the students in their daily lives. As a result, the conclusion is that the kiai's leadership pattern is religious charismatic-democratic.Kiai is a leader and determinant who, with his influence and power, can determine his steps and policies.