With the global economy becoming more integrated, the issues of cross-cultural relevance and transferability of leadership theories and practices have become increasingly urgent. Drawing upon the concept of parallel leadership in schools proposed by Crowther, Kaagan, Ferguson, and Hann as an example, the purpose of this paper is to examine the notion that Western educational leadership theories are universal in applicability in a Singapore school context. According to Crowther "et al.", parallel leadership is a process where school principals and teacher leaders engage in collective action to enhance school capacity through mutual respect, a shared sense of purpose and celebrating individual variations and differences. This interaction involves deep cognitive learning as well as social, moral, aesthetic and spiritual aspects of learning and development. By way of understanding of cultural values, it is not surprising to note that educational leadership theories are in fact "culture-bound". Culture is essentially related to environmental factors, assumptions and constraints. In other words, the cross-cultural transferability of educational leadership theories and practices is subject to the degree of similarities between the cultures. It is paramount to be cautious of the adoption of Western "cultural bound" theories in the local school contexts. (Contains 1 table.)