Although political skill and political will have been conceptualized as important predictors of performance and effectiveness in organizations for over three decades, virtually no research has investigated the respective roles played by these two constructs in explaining behavior in organizations. Because political skill and political will are believed to be inextricably intertwined, these two constructs should interact to explain organizational outcomes (e.g. job performance) better than either construct individually. However, the interaction effect may be more complex than we might initially believe to be the case. This chapter proposes a theoretical model and testable propositions regarding the roles played by political skill and political will, arguing for a moderated nonlinear relationship of political skill and will on job performance prediction. Additionally, in the future research directions section, we discuss how political skill, political will and political behavior work together to influence important work outcomes in organizations. Implications for theory and research and directions for future research are discussed.