In this article we examine the mentoring program for novice headteachers and what they perceive as its purposes, as well as the constraints to successfully implementing it in Malaysian schools. Using a survey research design we analysed responses from 200 newly appointed headteachers from two state departments of education, and interviewed six headteachers through two focus group interview sessions. As expected, headteachers revealed that mentoring had significantly improved their professional values as a school leader, and had led to the creation of a knowledge sharing culture that boosted their confidence level and improved their practical knowledge related to school leadership. However, headteachers also revealed that time constraints negatively impacted on the effective implementation of mentoring. The study also offers practical suggestions for the headship training system in Malaysian context.