AbstractThe persistence of a gender gap in academic medicine has been documented in thousands of studies in the last decade. Notable disparity between representation by men and women is present in leadership positions, invited keynote speakers, and publication counts. The COVID-19 pandemic provided an additional context for this disparity; while many journals continue to experience rapid increases in manuscript submissions, these submissions are disproportionately from men. The results of efforts aimed at raising awareness and advocating for women have been underwhelming. Allowing this disparity to continue significantly limits the diversity and quality of vision in leadership and research. We can—and must—do better. How do we bridge the gaps between intention, interpretation, and results? How can advocates ensure that they aren’t unintentionally creating situations that undermine the very women they seek to empower? Until these questions are answered, the goal of ending gender discrimination risks being unattainable. In this critical review we argue that the gender gap is a symptom of a much larger issue. Specifically, the power of social expectations, culture and gender stereotypes remains a resistant force against calls for action. The power of stereotypes shapes the decisions that men and women make about their careers. In turn, these decisions impact the amount of time that women can dedicate to leadership, self-promotion, and research. Drawing on our combined lived experiences and a rich multidisciplinary literature, we offer a practical guide to allies in the fight against the gender gap.