This paper explores the extent to which the leadership knowledge, skills, and abilities of upper-year student leaders on one private, United States college campus developed as a consequence of their education and experience as an extended orientation leader. Findings reveal that compared to leadership education in the classroom, leadership development is limited by experiences that do not include intentional reflection. We identify key elements in pedagogical frameworks that support and impede the leadership development of students and propose strategies to enhance the learning outcomes established for leadership development.