This article aims to contribute to an understanding of principalship in Hong Kong through probing the formation and preservation of the deep leadership structures that shape its practice. Deep structures are formed partly through a dynamic relationship between constitution and culture which forms bounded “codes” of understanding, conduct and behaviour which combine to shape principalship in Hong Kong and power relationships within schools and collections of schools. After providing a brief historical snapshot of Hong Kong education development since 1945, the paper explores the recent context of principalship and how this influences its shape in schools. Discussion of context focuses on the interconnected elements of constitution and traditional culture. These factors are illustrated using the issues of principal selection and teacher and parent empowerment to show the influence of deep leadership structures on the principal and the system. Depending on the perspective taken, these can be understood as either supportive or obstructive to better school leadership. Copyright © 2004 Taylor & Francis Ltd.