Through a collaborative autoethnographic approach, a former principal, current principal, current assistant principal, and aspiring principal recount their experiences pertaining to identification of leadership talent. As identified through previous research, proper identification or talent is the first major component to quality succession planning. Data were collected through individual reflections and group discussions and triangulated to published documents from the school district. Positive and negative aspects were identified, including personal experiences and perceptions of district-wide initiatives. Divergent viewpoints were most notable among levels of experience. The former principal focused on systems aspects, the current principals concentrated on aspects that affected them directly or in which they had influence. The aspiring principal addressed the issues from the point of view of a teacher who had limited exposure to several aspects. Limitations and potential biases were acknowledged and recommendations for future research were provided, including expansion as a case study or phenomenology.