["British Journal of Management, EarlyView. ", "\nAbstract\nThis paper revisits the entrepreneurial orientation–performance relationship in family firms by examining why entrepreneurial orientation yields uneven performance returns. Drawing on entrepreneurial orientation research, upper echelons theory and gender role theory, we argue that the effectiveness of entrepreneurial orientation depends on the CEO's ability to sustain entrepreneurial action. Using cross‐country data from family firms, we find that the positive effect of entrepreneurial orientation on performance is weakened under female family leadership. However, this effect is attenuated when the female family CEO is an only‐child and amplified in firms with multigenerational involvement. Overall, our findings show when and why gender at the helm matters for entrepreneurial success in family firms.\n"]