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We present a conceptual framework of situational moderators of gender/sex effects in negotiation, risk-taking, and leadership—three masculine-stereotypic domains associated with gender/sex gaps in pay and authority. We propose that greater situational ambiguity and higher relevance and salience of gender/sex increase the likelihood of gender/sex-linked behaviors in these domains. We argue that greater ambiguity increases the extent to which actors and audiences must search inwardly (e.g., mental schema, past experience) or outwardly (e.g., social norms) for cues on how to behave or evaluate a situation and thereby widens the door for gender/sex-linked influences. Correspondingly, we propose that gender/sex effects on behavior and evaluations in these domains will be more likely when gender/sex is more relevant and salient to the setting or task. We propose further that these two situational moderators may work jointly or interactively to influence the likelihood of gender/sex effects in negotiation, risk-taking, and leadership. We conclude by discussing applications of our conceptual framework to psychological science and its translation to practice, including directions for future research.