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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.

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.

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.

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.

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.

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.

Mentoring programmes for school administrators aim to facilitate learning by mentor‐protégé pairing. Selected vice‐principals are paired with experienced principals in protégé‐mentor pairs, for eight weeks of intensive mentoring in Singapore. Research suggests that mentoring programmes can be designed to benefit both mentors and protégés. Presents the results of a study on mentoring in Singapore. It highlights the benefits from mentoring and its correlates. Findings indicate that the behaviours and personal qualities of mentors and protégés could determine the benefits of mentoring.