Over the past 30 years, the nature of communication at work has changed. Leaders in particular rely increasingly on e-mail to communicate with their superiors and subordinates. However, researchers and practitioners alike suggest that people frequently report feeling overloaded by the e-mail demands they experience at work. In the current study, we develop a self-regulatory framework that articulates how leaders’ day-to-day e-mail demands relate to a perceived lack of goal progress, which has a negative impact on their subsequent enactment of routine (i.e., initiating structure) and exemplary (i.e., transformational) leadership behaviors. We further theorize how two cross-level moderators—centrality of e-mail to one’s job and trait self-control—impact these relations. In an experience sampling study of 48 managers across 10 consecutive workdays, our results illustrate that e-mail demands are associated with a lack of perceived goal progress, to which leaders respond by reducing their initiating structure and transformational behaviors. The relation of e-mail demands with leader goal progress was strongest when e-mail was perceived as less central to performing one’s job, and the relations of low goal progress with leadership behaviors were strongest for leaders low in trait self-control. (PsycINFO Database Record (c) 2018 APA, all rights reserved)