We draw on the agency and stewardship perspectives to determine whether and how the effect of family leadership on the entrepreneurial orientation-performance relationship in small and medium (SME) family firms is contingent on the main life cycle dimensions: firm size, generational stage, and board of directors’ engagement. The analyses of 284 Belgian family SMEs reveal that nonfamily leaders outperform family leaders in transforming entrepreneurial orientation into performance in larger firms, whereas family leaders outpace nonfamily leaders when the board has a strong engagement in serving the CEO.