The purpose of this study was to identify which factors can enable women to relate to and aspire for stereotype inconsistent roles, like leadership. Across two studies, we tested the effects of supervisor gender and supervisor characteristics (agency vs. communality) on women’s social comparisons (perceptions of similarity and identification with their supervisors), and in turn, their leadership aspiration. In our first experiment (N = 465) we found that women had higher social comparisons with female supervisors and with communal supervisors. In our second, survey study (N = 303) we found that women had higher social comparisons with communal supervisors irrespective of supervisor gender. Across both studies, we found that these social comparisons served as a mediator by which supervisor communality enhanced women’s leadership aspiration. By focusing on social comparisons as a psychological mechanism, we address the value of stereotype inconsistent supervisors as presenting women with the opportunity to relate to such exemplars and imagine themselves as occupying roles that dismantle existing gender-leader stereotypes through increased leadership aspiration. Keywords: gender stereotypes, supervisors, communality, social comparisons, leadership aspiration