<![CDATA[ This study examined the role of the leader of Pondok Pesantren Assanamiyah in developing santri life skills and identified the leadership pattern that supported the program. A descriptive qualitative approach was employed. Data were obtained through in-depth interviews with the pesantren caretaker and two santri, direct observation of daily activities, and documentation. The data were analyzed through reduction, data display, and conclusion drawing. The findings indicated that leadership was manifested through educational, administrative, motivational, supervisory, innovative, and evaluative functions. Life-skill learning was embedded in everyday pesantren activities, including farming, cooking, cooperative management, small-scale trading, and entrepreneurship practice. The leader's style was characterized as charismatic-participative: the Kyai served as a visible role model while maintaining open communication and involving ustadz and santri in program implementation and evaluation. The approach supported independence, discipline, confidence, teamwork, and entrepreneurial orientation. The main constraints were limited digital facilities and business capital]]>
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