Using medical residency as an example, this paper explores gender disparities in evaluations as individuals transition roles from student to health care professional and whether differences in resident performance (rather than differences in perceptions of performance) contribute to gender disparities in evaluations. The authors found that men and women are reviewed as equally capable at the beginning of residency, but by year three after roles shift from ‘student’ to ‘colleague’, men are perceived as outperforming women. When comparing feedback on medical errors, women receive more harsh criticism and less supportive feedback than men by year three of residency.