The current research challenges the assumption that the presence of women in leadership positions will automatically "break the glass ceiling" for other women. We contend that it is not just a female leader's presence, but also her performance, that influences evaluations of subsequent female candidates for leadership positions. We argue that the continued scarcity and perceived mismatch of women with high-level leadership increases gender salience, promoting perceptions of within-group similarity and fostering an evaluative generalization from the performance of a female leader to the evaluations of another, individual woman. In 5 studies, we demonstrate that the effect of exposure to a female leader on another woman's evaluations and leadership opportunities depends on whether she is successful or unsuccessful (Study 1) and whether she confirms or disconfirms stereotype-based expectations about women's leadership abilities (Study 2). Supporting the role of gender salience and shared group membership in the process, we show that this effect occurs only between women in male gender-typed leadership roles: Evaluative generalization does not occur between women in contexts that are not strongly male in gender type (Study 3) and is not observed between men in male-typed leadership (Study 4). We also explore whether there is evaluative generalization between male leaders in a female-typed context (Study 5). Our results suggest that overcoming gender imbalances in leadership may not be as simple as targeted placement, and that having women in high places should not induce complacency about the elimination of gender bias. (PsycInfo Database Record (c) 2021 APA, all rights reserved).