Building upon and extending Parker, Bindl, and Strauss’s (2010)theory of proactive motivation, we develop an integrated, multilevel model to examine how contextual factors shape employees’ proactive motivational states and, through these proactive motivational states, influence their personal initiative behavior. Using data from a sample of hotels collected from 3 sources and over 2 time periods, we show that establishment-level initiative-enhancing human resource management (HRM) systems were posi- tively related to departmental initiative climate, which was positively related to employee personal initiative through employee role-breadth self-efficacy. Further, department-level empowering leadership was positively related to initiative climate only when initiative-enhancing HRM systems were low. These findings offer interesting implications for research on personal initiative and for the management of employee proactivity in organizations.