Purpose – This study aims to examine the representation of inspirational leadership in pondok pesantren in response to the limited phenomenological studies on the experiences of pesantren leaders in interpreting amanah, role modelling, service, values, sources of inspiration, obstacles, resolution strategies, and their impact on santri and pesantren institutions.Methods/Design/Approach – This study employed a qualitative phenomenological approach. Data were obtained through semi-structured interviews with 16 pesantren leaders in Java and the Special Region of Yogyakarta, selected purposively, who had leadership experience ranging from 2 to 30 years. The data were analyzed through repeated reading, mapping of meaning units, coding, cross-informant comparison, theme clustering, and phenomenological reflection.Findings – The study generated six main themes: leadership as amanah, service, and role modelling; value foundations based on the Qur’an, hadith, sharia, dawuh kiai, institutional rules, ethics, and musyawarah; sources of inspiration from the Prophet Muhammad SAW, kiai, nyai, teachers, parents, and national figures; practices of communication, coordination, task distribution, musyawarah, and evaluation; obstacles in the form of miscommunication, discipline issues, limited human resources, social change, santri dynamics, wali santri, and administrators; and impacts on santri character, organizational order, sense of belonging, and institutional strengthening. Resolution strategies were carried out through communication, tabayyun, musyawarah, evaluation, mentoring, and strengthening administrators’ commitment.Originality/Value – This study offers the concept of amanah-relational leadership, which explains pesantren leadership through the internalization of amanah, the performativity of role modelling, caregiving service, collective musyawarah, and institutional adaptation.Practical Implications – The findings underscore the need to strengthen the moral-spiritual, managerial, and adaptive capacities of pesantren leaders to improve communication, accountability, santri protection, program evaluation, and educational governance based on pesantren values.Keywords pesantren leadership, amanah-relational leadership, phenomenology, Islamic education, inspirational leadership.Paper type Research paper