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Small businesses in developed countries are facing the aging of owners who will soon leave the businesses. Rethinking small business succession is crucial to ensure continuous entrepreneurial orientation (EO) improvement and business success. The entrepreneurship literature argues that small business owners often transfer their businesses to external successors. These successors are more inclined to implement fresh initiatives oriented toward EO. Nevertheless, little is known about the characteristics (that is, the personality traits and cognitive abilities) of the external successors who may exhibit high EO. Relying on the upper echelon perspective, our study closes this gap by clarifying how the personality traits (i.e., creativity and general self-efficacy) and cognitive ability (i.e., entrepreneurial alertness) of external successors exhibit the high EO of small businesses. Our structural model is tested with 310 French external successors in small businesses. The results show that the creativity and alertness of external successors not only positively and directly influence the EO of a small business but also fully mediate the positive effect of general self-efficacy on EO. These findings highlight the roles of external successors’ personality traits and cognitive ability in seeking new business opportunities and revitalizing the transferred business.