The more than two decades of scholarly research on emotional labor has been skewed towards service workers with the dominant view that engagement in emotional regulation impairs service workers’ well-being outcomes. Despite the potential knowledge gain of examining the role managerial emotion regulation plays in leadership of employees, the call for further study of its effect in managerial and leadership contexts has largely been unattended. Based on the findings of two studies, this research reports the interpersonal benefits of leader deep acting on employee outcomes without adversely affecting leaders’ within-person well-being. Using self-reported survey data (n = 175) collected from the employees of a mid-sized, reputable financial company, the findings from study 1 suggest that employee perception of leader deep acting was favorably related to employee job satisfaction and perceived leadership effectiveness; these relationships were mediated by employee perception of leader authenticity. In study 2, using managers of the same financial company as a sample (n = 81), diary data (experience sampling from 5 consecutive days) showed a significant positive relationship between leader surface acting and emotional exhaustion, with the relationship being mediated by daily emotional dissonance. However, as predicted, daily leader deep acting was not found to be related to leader’s daily well-being outcomes of emotional dissonance and emotional exhaustion. Combined, our two studies demonstrate that managers’ use of deep acting has the potential to favorably impact employee outcomes without impairing their (managers’) well-being.