In this article, we investigate the effects of leader subjective ambivalence on team performance. Integrating the ambivalence literature and social learning theory, we propose a multi-level model of whether, when, and why team leaders’ subjective ambivalence enhances team performance outcomes. The results of two laboratory experiments (Studies 1 and 2) demonstrate initial support for the relationship between leader subjective ambivalence and information-seeking behaviors. The results of a longitudinal field study (Study 3) based on 164 projects (164 leaders and 725 subordinates) show that leader subjective ambivalence has a positive indirect effect on team task performance first through leader information-seeking behaviors and later through team information-seeking behaviors. Our results further indicate that project complexity is a boundary condition for the proposed conditional indirect effect of leader subjective ambivalence on team performance outcomes. We discuss the theoretical and practical implications of these findings.