Given that the concept of community college in Hong Kong has only been introduced 10 years ago, with the new “3-3-4” education structural reform, the leadership in community college will become more challenging. In this paper, the aim is to provide a personal philosophy on how educational leaders should lead in community college settings given the highly diverse student backgrounds. The perspective of why we, as educational leaders, should reflect, reconstruct, and reengineer on community college leadership will be discussed. We will give insights on how different it is between leading in university and in community college, particularly in Hong Kong. Common issues and difficulties encountered by top managements, supporting staff, teachers, and students are identified and explained. The importance of relationship and dialogues in our context of building a true community is presented. The paper will conclude with the notion of how an authentic leader should be in leading community college in Hong Kong. It is expected that the direction of this personal philosophy will have a major impact in the both local and global leadership in education.