This article provides evidence and generates insights about the power of financial rewards to motivate school administrators and the design features that influence their motivational potency. The multi-year mixed-methods study is grounded in expectancy and goal setting theories that suggest (a) awards must be salient and sizable enough to appeal to educators; (b) the award structure must evidence credible connections between work, performance, and reward; and (c) goals, measures, and awards must be perceived as fair. Since this framework helps explain administrators' mixed reactions to their awards, it could help guide future efforts to develop and evaluate administrator incentive programs.