The research questions posed in this study highlight the importance of valuing proactivity in both prompting an individual to engage in proactive behavior and encouraging the expression of that behavior. We integrate a variety of constructs from the proactivity literature to gain a deeper understanding of proactive behavior as it relates to proactive motivation and supervisory performance evaluations. First, we draw upon self-determination theory, expectancy–value theory, and the recent integration of the proactive motivation literature to hypothesize that proactive behavior is predicted by the interaction of “can do” and “reason to” proactive motivational states. Second, on the basis of performance theory, we hypothesize that the relationship between proactive behavior and performance depends upon the extent to which the supervisor values proactivity. Specifically, we argue that supervisors with proactive personalities are more likely to value and reward subordinate proactive behavior than passive supervisors. Results provide support for both of our hypotheses. Interestingly, results show that proactive behavior did not result in negative consequences but rather that there was a cost (i.e., lower performance rating) for not taking charge for employees with proactive supervisors. Copyright © 2012 John Wiley & Sons, Ltd.