What influences individuals in pursuing leadership positions in a Catholic school? The particular needs and perceptions of teachers and administrators regarding current and future leadership development practices were gathered to address the question. Of particular interest were the deterrents and barriers that are keeping potential candidates from aspiring to leadership positions in this particular school board.Interviews, focus groups, and a survey were tools used to discover the perceptions of academic staff including senior administrators, principals, consultants/co-ordinators, and elementary and secondary teachers. Most prominently,it was felt that the expectations of the role needed to be more realistic and there needed to be significant leadership training to develop skills necessary to understand and manage the job. Exploring different leadership models including the concept of distributed leadership and the concept of servant leadership were recommended as next steps. When developing policies and strategies to encourage more people to apply for the principalship, a focus on internal rewards more than external rewards was also recommended.