SummaryParadox theory suggests that contradictory demands, like applying current work methods while exploring new ones, should be viewed as dualities with competing and complementary aspects. It advocates for employee ambidexterity, where employees must manage exploitation and exploration. We know little about how personal dispositions affect ambidexterity independently or when interacting with situational factors. Based on a time‐lagged survey of 364 employee–supervisor pairs from 74 R&D teams, we found that proactive disposition was positively related to ambidexterity, enhancing creativity. Guided by trait activation theory, we found further that paradoxical supervision and job autonomy enhanced the relationship between proactive disposition and employee ambidexterity and the indirect effect of proactive disposition on creativity via ambidexterity. We discuss these findings' theoretical and practical implications, extending the literature on proactivity, ambidexterity, and paradox theory.