Problem The important role played by executive coaching in the development of leaders is well established in the literature. While some scholars suggest that executive coaching fosters transformative learning (TL), there is insufficient empirical evidence to support this. Solution This study set out to investigate the process of TL in executive coaching from the coachee’s perspective. A longitudinal multiple case study was adopted to examine how three key transformative learning elements—disorienting dilemma, critical reflection, and rational dialogue—occurred in an executive coaching engagement and the learning outcomes that emerged. A key finding was that, in addition to the three accepted elements, there is a fourth element (acceptance) that precedes the rational dialogue. The results of this study informed the development of a transformative learning model, which could guide future research, theory, and practice in the field of human resource development (HRD). Stakeholders The study will benefit scholars and practitioners in the fields of human resource development, executive coaching and leadership development.