Purpose: This paper aims to explore coaching as an approach to developing school leaders in the Singapore education system. It takes a close look at the nature of coaching experiences of beginning principals and principal-trainers, as well as the related benefits and challenges. Design/methodology/approach: A qualitative inquiry approach was adopted, and four beginning principals and three principal-trainers were interviewed. An emergent coding method was deployed in data analysis. Findings: Beginning principals described a positive, helpful and empowering coaching experience when coached by principal-trainers. The latter skillfully asked questions in a safe, non-threatening space for deeper self-reflection. In the process, beginning principals gained greater self-awareness and self-empowerment, and appreciated the shared context of school leadership. While coaching is a useful leadership development approach, inherent implementation challenges were identified. Research limitations/implications: Coaching as a system-wide strategy to support school leaders in Singapore has only recently been implemented. Further research using a larger sample is recommended as coaching becomes more pervasive. Practical implications: The findings revealed a compelling case for a more pervasive adoption of coaching as an approach to support leadership development. Coaching facilitates effective school leadership, and there is scope for self-coaching, peer coaching and coach supervision of principals, middle leaders and classroom teachers. Originality/value: This paper highlights the nature and positive impact of principalship coaching within a specific policy and cultural context of the Singapore education system. It adds to the body of literature on principal preparation, development and support.