This study presents the transformation of the kiai's leadership in forming regeneration and developing Islamic boarding schools in Al Ummah Islamic Boarding School Sukabumi. This research uses a qualitative approach with the type of case study research, which focuses on the leadership portrait of the kiai, the mechanisms and steps for the operationalization of leadership, and the process of changing leadership. Data collection was carried out in 2018 by interviewing kiai, kiai families, students and community leaders. The results showed that the portrait of kiai leadership at Pesantren Al Ummah Sukabumi is oriented towards a democratic leadership style, which is the operationalization mechanism for the transformation of private ownership into institutional property, curriculum development, and infrastructure development. This is based on the replacement of kiai who have died, replaced by kiai families who have a holistic orientation and understanding in developing future pesantren. Recommendations from the results of this study are the importance of developing Islamic boarding schools which are not only oriented towards religious development, but also fostering students to have skills that will become their life provisions in the future.