Although evidence indicating the positive implications of servant leadership abounds, we currently lack knowledge of how we can promote servant leadership at work. Drawing on the functional theory of counterfactual thinking, we propose that servant leadership can be fostered with the use of counterfactual thinking (CT) interventions (i.e., by inducing leaders to think about how they could have behaved differently toward their followers in order to have better served their needs). We further contend that the positive impacts of CT interventions on leaders’ servant leadership transmit to followers’ thriving and servant leadership toward others. However, we maintain that such impacts can be stronger for leaders higher on prosocial motives, as their concerns with benefiting others encourage them to practice insights derived from CT interventions. To test the hypotheses, we conducted two field studies, utilizing a pre–post experimental–control group design. The samples were drawn from Prolific and various companies located in South Korea. We obtained support for the positive influences of CT interventions on leaders’ engagement in servant leadership and its two key outcomes (i.e., followers’ thriving and servant leadership toward others). However, the moderating role of leaders’ prosocial motives was not supported. Overall, this research provides evidence that organizations can promote servant leadership and reap its key benefits using CT interventions.