Findings from this six-year study point to the challenge of providing substantive and on-going feedback to students in a non-traditional leadership preparation program. More importantly, this paper describes, from an inside-out perspective, the struggles encountered as faculty attempted to remedy inconsistencies in the program and reconcile differences during a ten-year period. Cognizant of the importance of engaging in a critical reflective practice, they struggle to navigate the ambiguous path between the department's norms and culture and the values and beliefs gleaned from their own preparation experiences. This study also examines my own my personal journey as researcher and faculty member. Recognizing that the focus on the program's gaps was short-sighted, I began to appreciate that program implementation and institutionalization were developmental processes with discernable stages, occurring in real time. In turn, I pose several questions for faculty to consider as they engage in modifying leadership preparation programs.