In recent years, personal initiative has been found to predict job performance. However, implicit in this direct initiative–performance relationship are more complex process dynamics that can be better understood when contextual antecedents, moderators, and mediators are considered. Drawing from perspectives of proactive behavior as a goal-directed process, a research model of personal initiative was tested in a three-study investigation intended to build upon and advance prior work. Specifically, the model indicates that climate for initiative interacts with the social astuteness dimension of political skill (i.e., opportunity recognition) to influence the demonstration of personal initiative, and this first part of the model is tested and supported in Study 1. Then, personal initiative is hypothesized to interact with the interpersonal influence dimension of political skill (i.e., opportunity capitalization) to predict supervisor assessments of job performance, and this part of the model is tested and supported in Study 2. Study 3 provided a test of the entire model and demonstrated support for moderated mediation, thus adding increased confidence in the validity of the theory and findings through constructive replication.