Our paper considers a critical juncture in community college leadership as many community college leaders approach retirement. These transitions are inescapable. How will institutional memory (Parker, 2011) be preserved with the passing of the leadership mantel to a new generation? These transitions also impact ways in which leaders influence student success, institutional mission, and the overall health of the institution (Boggs, 2011). We view these leadership transitions through the lens of Appreciative Inquiry (AI). We ask: How might AI be utilized to successfully navigate community college leadership transitions? Examining two cases where AI was applied within higher education environments, we discuss the potential for such a model to effectively address pending leadership changes within the community college environment. These cases illustrate ways in which AI has been applied in different institutions, yet each provides insight into the ways AI may ameliorate knowledge transfer through narrative and storytelling. We suggest that AI has the potential to address multiple facets of leadership transition and facilitate the development of contextual competency.