In Taiwan, Catholic schools are now facing a crisis of leadership as the available number of priests and nuns who are able to lead these schools is declining rapidly. The question is now being asked as to whether the ministry of the Catholic school’s mission can be sustained as more and more lay principals are needed and appointed to replace principals affiliated with religious orders. This basic question led to an exploration of three research questions. First, what differences, if any, are there between religious and lay middle school principals in terms of servant leadership? Second, what are the differences, if any, between religious and lay leaders in the promotion of the traditional Catholic school mission? Finally, what differences are there, if any, between school cultures in Catholic Middle Schools when led by either a religious or lay principal? Results shows that in order to continue this process it is recommended that Catholic Middle school principals should participate in servant leadership workshops and/or communications training in order to foster open communication, empower the vision and create mutual trust between principals and school staff. The goal would be to develop and maintain a school culture that reflects the Catholic heritage of the school. In addition, staff rotation and mentoring should be implemented to ensure that experienced teachers participate in school affairs and help build school spirit and culture in order that the school’s educational mission can be maintained. Finally, a team should be built within the schools in order to develop servant leadership skills in all members of the school.