Although providing negative performance feedback can enhance employee performance, leaders are sometimes reluctant to engage in this activity. Reflecting this, prior research has identified negative feedback provision as an aversive, yet potentially rewarding, managerial activity. However, little is known about how providing negative feedback impacts the effectiveness of leaders who do so. To shed light on this issue, we develop and test a theoretical model that identifies how leaders' proximal and distal reactions to providing negative feedback are contingent upon their levels of trait empathy. Supporting our theory, results from an experience sampling study indicate that leaders higher in trait empathy report feeling both less attentive and more distressed after providing subordinates with negative feedback, whereas leaders lower in trait empathy report feeling more attentive and less distressed. Attentiveness and distress, in turn, were associated with leaders' daily perceptions of their effectiveness; distress was also associated with leaders' daily enactment of transformational leadership behavior. Results of two subsequent studies focused on single episodes of negative feedback provision revealed that trait empathy amplifies the extent to which feedback recipients' negative emotional reactions impact additional leader effectiveness criteria (e.g., executive functioning and planning/problem-solving), further supporting the need to account for the crucial role of trait empathy in the feedback-provision process. Altogether, our research provides a novel perspective on the feedback-giving process by shifting the focus of theorizing from the recipient to the provider, while challenging current thinking about leader empathy by highlighting its potential downside for leadership. (PsycInfo Database Record (c) 2022 APA, all rights reserved).