Leaders often find themselves in complex situations in which they must navigate competing and contradictory demands. Consequently, leaders often experience ambivalence. While followers pay close attention to leaders and use their leaders’ behaviors and emotions as cues for modeling their own behavior, there is little empirical work exploring how followers perceive leader ambivalence and how these perceptions affect followers. Therefore, in three studies (total N = 879), we examined whether perceiving leader ambivalence could facilitate followers’ willingness to speak up. We also investigated the underlying mechanism of this effect, testing whether perceptions of leader ambivalence led to inferences of both higher leader cognitive flexibility and responsiveness, which then would increase the likelihood that followers speak up. In line with our hypotheses, followers showed a greater willingness to speak up when perceiving an ambivalent leader than a non-ambivalent leader. This effect was serially mediated by perceptions of both increased leader cognitive flexibility and responsiveness. Study 3 also showed that when followers perceived an ambivalent leader, they expected fewer negative consequences when speaking up about a variety of issues (e.g., response to dissatisfaction). We discuss the implications of our findings for future research on ambivalence in leadership and organizational contexts.