Pondok Pesantren Modern Muhammadiyah Boarding School Yogyakarta (PPM MBS Yogyakarta) is one of Islamic Boarding Schools that educate Muhammadiyah cadres to continue dakwah (preaching) Muhammadiyah. The research aimed at learning about the supervision strategy used by PPM MBS in improving santri’s (students of Islamic boarding school) competence to manage dakwah Muhammadiyah, learning about the inhibiting and supporting factors of the supervision strategy, learning about the solutions found to overcome the obstacles during the process of improving santri’s competence, and learning about the improved competence of santri in order to manage dakwah Muhammadiyah. The research was conducted using descriptive qualitative approach and the data were collected through interview, discussion, and documentation. The research results indicate that PPM MBS uses approach, understanding, and punishment strategy in order to educate Muhammadiyah cadres who have great characters as expected by PPM MBS. There are two inhibiting and supporting factors which are external and internal that consists of santri, santri’s parents, teacher, and the community around the boarding school. PPM MBS provides solutions by improving the quality of the teachers, intensely evaluating each activity, and educating santri and the parents about boarding school. The competences to improve are individual ability, matters about organization, and knowledge on Muhammadiyah organization.