The focus of this article is student leadership and student leadership development in a Catholic secondary school. Central to the article are the leadership experiences and self-perceptions of elected students aged 1517 years as they participated in the school’s leadership program. These insights helped the researcher discern beneficial outcomes for elected leaders, and highlight areas of concern for staff responsible for student leadership initiatives to consider. The research focused on a longitudinal case study where data were gathered through the exercise of multiple, qualitative methods, namely: one-on-one interviewing, focus group interviewing, document searches, field notes, and researcher reflective journaling. A summary of findings indicated perceived positive, challenging and negative experiences as reported by the elected student leaders. These findings contribute to the growing body of school-based leadership literature, and may inform school leaders and staff responsible for the development of student leadership potential.