The purpose of this research is to capture and interpret the stories of “outsider” managers who make the transition to the public sector. These experiences are considered in the context of efforts to shift public management culture in a direction consistent with meeting contemporary demands placed on public sector organisations. It is often noted that an important strategy for changing culture is the infusion of outsiders. Outsiders are thought to bring new perspectives that, through a dialectical process (Van de Ven 1995), create the potential for change. While there have been cross-sector comparisons (Broussine 1990; Silfvast 1994; Redman 1997), little attention has been given to the experience of those who make the transition in the context of efforts to reform public sector management culture. Not only is the infusion of private sector managers into the public sector a potential culture change strategy, it is also a personal experience for those who make the transition. Boundary crossing is typically an anxiety provoking experience (Van Maanen & Schein 1979) and the quality of this experience influences decisions to commit, engage, disengage or exit. The quality of the experience is likely to be affected by how the public organisation responds to people making this transition, that is, their investment in people processing (Saks 2007). The cost of recruitment and selection processes at middle and senior management levels warrants a greater research focus on this transition. In this paper we argue that the experiences of those who make the transition from private to public sectors has much to tell us about the traps that transition managers experience in making this change, the implications for injecting outsider managers as a strategy for achieving public management culture change, and how reform-oriented public organisations can manage the transitions of outsider managers into the public sector in order that best value might be achieved for both the individual and organisational change goals.