We use affect control theory (ACT) and its computer simulation program, Interact, to theoretically model the interactional dynamics that women and men business executives are likely to face in the workplace, and we show how these dynamics may contribute to the gender gap in business leadership. Using data from 520 simulated events and two analysis strategies, we use ACT to develop empirically grounded hypotheses regarding these processes. The simulations suggest that women executives face a wider range of situations that require gender deviance than men executives, many of which may be unavoidable (e.g., confronting an unreliable employee). They also suggest that observers will attribute negative characteristics to both women and men executives who engage in a gender-deviant action but that the characteristics attributed to gender-deviant women executives (e.g., ruthless, sadistic) move their identity further from the affective meaning of “an executive” than the characteristics attributed to comparably gender-deviant men executives (e.g., awestruck, gullible), patterns that are likely to make the path to and retention of business leadership positions more difficult for women. We also discuss how our approach could be used to theorize about interactional processes underlying other inequalities, including those based on race, ethnicity, class, sexual orientation, disability, and age.