The experiments presented here examine how managers and executives can improve the effectiveness of their negative written communications (i.e., refusal of employees’ requests) by incorporating the concept of fit into their message framing. By applying regulatory focus theory, the authors suggest that an outcome-based fit between the message and the recipient leads to more favorable work outcomes. The results of Experiment 1 show that employees retain greater feelings of psychological empowerment when they receive a written refusal framed in terms that match (versus mismatch) their current regulatory focus. Moreover, data from Experiment 2 demonstrate that employees perceive a written refusal as more fair when it is framed in terms that match (versus mismatch) their activated regulatory focus. However, this effect was not found when an employee’s request was approved, an observation that stresses the importance of regulatory fit in negative managerial communications specifically. Finally, this article discusses management implications for designing successful negative written managerial communications.