To date, few studies empirically have confirmed the long-accepted notion that politically skilled individuals discriminately and strategically employ or avoid particular political behaviors in the workplace. The purpose of this multi-study investigation is to evaluate political skill and political will as antecedents of configurational impression management strategies. The configurations of impression management tactics found by Bolino and Turnley (2003) are confirmed using hierarchical and K-means cluster analysis, and discriminant analysis is employed to demonstrate the effects of political skill and political will above and beyond the effects of Machiavellianism and self-monitoring in the prediction of impression management configurations. Consistent with the two-component model of impression management (Leary & Kowalski, 1990), the results of these studies confirm that political will and political skill best represent the cognitive processes that enable impression management strategy selection. Post-hoc analyses illustrates that there may be slight differences in usage of some impression management tactics directed at specific targets (in two of our four samples). Implications, limitations, and future directions are discussed.