Principal preparation around the development of reflective practices has traditionally focused on the individual reflective practices of principals. Recently, reflective discourse between principals and students has facilitated principals' understanding of student perspectives regarding school policies and processes. We explore the use of digital video to facilitate principal and student reflection by recasting reflection as a collaborative process in which collective understandings are developed through reflective discourse. Specifically, this participatory action research (PAR) approach examined a case example of the Iterative Digital Reflection (IDR) process between a high school principal and a 9th grade student that focused on practices, processes, and programs that they perceived to facilitate student college preparedness and readiness. (Contains 1 figure.)