This article reports an investigation into societal and organizational cultural influences on academic leadership in Saudi Arabian higher education, a previously underexplored area. In Saudi Arabia, it is currently unclear how university deans are negotiating the balance between organizational cultural values and contemporary influences, and how the values they embrace may influence their leadership practices and effectiveness. The study has been conducted in eight main governmental universities under the Ministry of Education. Qualitative data has been collected, involving interviews with fifteen university deans, with data scrutinized by an interpretive thematic analysis. The deans’ responses indicated dissatisfaction with the broad societal culture around them and the negative influence this had on leadership practices. Tensions were apparent between traditional values and change, and the influence of family and tribal backgrounds. Five organizational cultural themes were identified as influences on deans’ leadership—a centralized environment, strict regulations, the authority of top management, selection and promotion issues, and reputational factors. The study’s outcomes contribute to the understanding of leadership perceptions and practices within a particular cultural context.