General Background Islamic boarding schools are institutions that have survived from the birth of the nation to significant changes in the era of globalization, keeping up with progress and continuously improving quality in education. Specific Background This study examines how kyai management creates role models for the discipline of santri and the wider Islamic boarding school community at Pondok Pesantren An-Nur Sidoarjo. Knowledge Gap Previous research lacks comprehensive qualitative analysis detailing the specific administrative phases, main operational components, and supporting or inhibiting factors of kyai leadership in enforcing institutional discipline. Aims This research aims to find out how kyai management creates role models for the discipline of santri and the wider Islamic boarding school community. Results The qualitative descriptive research shows that the main aspects of discipline creation comprise the kyai serving as a role model (uswah), formulating and socializing regulations, conducting evaluations, and providing rewards and punishments, supported by unified instructions and parental advice, alongside challenges from a lack of self-awareness and security control. Novelty The integration of a four-phase management approach (Planning, Organizing, Actuating, Controlling) directly led by a charismatic kyai establishes a robust framework for instilling structured religious and behavioral discipline. Implications These findings indicate that structured managerial leadership by religious figures can effectively maintain institutional longevity and cultivate high moral standards among students in traditional educational environments. Highlights: Kyai implement structured planning, organizing, actuating, and controlling frameworks to sustain institutional order. Primary disciplinary mechanisms involve exemplary modeling, systematic rule socialization, periodic evaluations, and balanced rewards and punishments. Administrative success relies heavily on unified leadership instructions and parental guidance despite individual student self-awareness challenges. Keywords; Ldeadership, Kyai, Islamic Boarding School, Discipline, Management