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This paper explores principals’ leadership journeys in response to issues in increasing diverse settings of public schools in an evolving social context in terms of demographic and culture changes in Hong Kong, an Asian Chinese society. The research questions are: What issues do principals identify as arising from the schools’ transformation in response to the changes? How do principals practise democratic leadership for school improvement in the increasing diversity of student population? This paper is a cross-case study of four principals’ leadership journeys through a theoretical lens of democratic leadership. The principals foster a lateral practice of democratic leadership in the diversity. The findings contribute to international accounts of reconnecting democratic leadership practices towards a collaborative context of multicultural inclusion.