With a mixed-method approach, this study explores how a Chinese CEO’s Confucian values shape and influence his/her firm’s digital transformation. In Study 1, we use semi-structured interviews with seven CEOs from various industries in mainland China. We reveal two value dimensions in Confucianism: the mindset of hierarchy and the knowledge-seeking mentality are particularly relevant to digital transformation. In Study, 2, we collect data from a survey of 207 CEOs of Chinese firms. Our empirical findings suggest that a mindset of hierarchy negatively affects digital transformation propensity, while a knowledge-seeking mentality positively influences it. Moreover, a weak legal environment amplifies the negative impact of hierarchy and strengthens the positive effect of knowledge-seeking, while market turbulence weakens the influence of knowledge-seeking mentality on digital transformation. To combine both qualitative and quantitative findings, this study illustrates cultural ideologies as critical antecedents to digital transformation and highlights the complex interplay between executive values and external environments in driving strategic change.