The roles of principal leadership in change management have long been documented. The key concern to examine in this study was the dilemmas and measures confronting principals' when they led changes to instigate inclusive education in Hong Kong. Thus, this paper aims to report sources of dilemmas and how principals tackled them in the change process. Ten principals of schools recognized for effective inclusive education practices were interviewed in a qualitative study. Findings suggested that the process of leading change was very complex. Two dilemmas were identified: (a) principals' struggles between benefits and issues of participating in inclusive education and (b) autocratic initial decisions versus need for staff involvement. The second dilemma stemmed from not involving key staff while the implementation required their active participation. Thus, the existing organizational culture and personnel capacities became obstacles required for the success of inclusive education. The leadership measures to tackle the obstacles began by building a shared vision which in turn required both transactional and transformational leadership activities in order to increase teacher commitment to reforms. This study has contributed to change leadership theories in affirming the need to include socio-political contexts in examining leadership decisions toward school reforms.