Experiential avoidance is defined as a process involving excessive negative evaluations of difficult or unwanted feelings, thoughts, and sensations, an unwillingness to remain in contact with and express these experiences, and habitual attempts to avoid or control them. Experiential avoidance is closely associated with maladaptive functioning. Although the ability to connect with internal experiences has been considered an important element of effective leadership, this assumption has not yet been empirically tested. On the basis of the Acceptance and Commitment Therapy model of experiential avoidance and the propositions of leadership models (e.g., transformational and authentic leadership) that characterize leadership as an emotion-related process, we examined the relationship between leaders’ experiential avoidance and their followers’ well-being in a sample of leader-follower triads. Well-being outcomes were subjective happiness, purpose in life, and job satisfaction. We also tested the mediating roles of followers’ basic psychological need satisfaction and need frustration in this relationship. Multilevel mediation model analyses suggested that followers’ psychological need frustration but not need satisfaction mediated the relationship between leaders’ experiential avoidance and followers’ well-being outcomes. Thus, a rigid attitude toward one’s internal experiences as a leader is a risk factor for followers’ well-being because leaders with such attitudes may pay little attention to their followers and give rise to need frustration in their followers. Organizational efforts to increase leaders’ flexibility in dealing with negative experiences can help foster well-being among both leaders and their followers.