Women make up less than 5% of the highest levels of organizations in the United States (Branson, Chen, & Redenbaugh, 2013; Zarya, 2016). The current study focuses and builds upon previous research on one significant contributor to the lack of gender parity at the top levels of management: discrimination due to stereotyping (Hoobler et al., 2011; Martell, Parker, Emrich, & Crawford, 1998; Schein, 2001). Furthermore, the current study examines the role of a specific day-to-day interaction on a female subordinate’s perceived promotability (i.e., pushing back on a task-related request from her superior). To that end, participants were recruited online, instructed to take on the supervisor role, were assigned to one of three experimental conditions (i.e., acquiescing, negotiating, and refusing), viewed illustrated video clips, and provided their assessments of a female subordinate’s promotability. Results indicate that the female subordinate was perceived to be the most promotable when she acquiesced, followed by when she negotiated the task-related request. Refusing the request resulted in the lowest perceptions of promotability. These findings suggest that a female subordinate’s perceived promotability is influenced by the extent to which her behavior aligns with the female stereotype.