The purpose of this study is to explore how leader humility contributes to the success of digital transformation (DT). With the rapid advancements in digital technologies, organisations are under increasing pressure to engage in DT to remain competitive. Leader humility has been recognised for its positive impact on DT outcomes; however, empirical studies are yet to be conducted to understand how leader humility contributes to DT success. This qualitative single-case study used semi-structured interviews with 17 participants from a large Aotearoa New Zealand-based higher education institution to answer the following research questions: (a) What contributes to successful DT; (b) What role does leader humility play in achieving success. The interviews captured the perspectives of end users, DT experts, and humble leaders involved in DT, offering a nuanced understanding of the role of leader humility in achieving successful DT from diverse perspectives. Data were analysed using reflexive thematic analysis. The findings suggest that successful DT is a people-centred change process that integrates technology with user capabilities. Leader humility humanises this process by emphasising the role of employees, who are integral to what successful DT entails. This study contributes to the growing body of research on successful DT, leader humility, and organisational change management, providing practical implications for leaders and HR practitioners in developing and supporting humble leaders to navigate the disruptions of DT.