This study explores the current transition of Israel's retired military officers from a military career to a second career in educational settings, particularly to principalship roles. Using a case study approach, the author illuminates how a retired military officer serving as a high school principal engages in the deliberative process (a communal experimental process designed to examine the consequences of actions under consideration) to solve a significant school problem. Throughout the 1999-2000 academic year, various voices surfaced with regard to the deliberative process of solving a significant problem of a rising level of violence facing a unique south Tel-Aviv (Israel) high school. The scarce research on the transition of retired military officers to the realm of education is presented, followed by emergent themes that illuminate how the principal, as a newcomer to the educational system, perceived schoolwork in general, and the deliberative process in particular. In that regard, sharing and incorporating multiple perspectives in the deliberative process, deliberating under the clouds of uncertainty and modelling a continuous learning process towards refining the school's functioning were strongly emphasized by the principal when deliberating on the alarming level of violence in school. In the light of the unstable, complex and changing educational context, the study offers insight to both policymakers and school communities on the possible impact of retired military officers occupying administrative positions in schools.