The term ‘interculturalism’, referring to exchange and dialogue between cultures outside the nation state, has become more frequent in the literature reflecting shifts in cultural patterns arising from increased globalization and population movements. In recent decades such shifts have resulted in significant changes in worldwide education systems, influenced by policies and practices of neoliberalism (Mullen et al. 2013). A corresponding process of internationalization particularly in higher education (HE) has seen greater student diversity in HE classrooms following the outflow of students moving from their countries of origin to the ‘market’ of international universities, and a corresponding pattern of inflows of international expatriate faculty into rapidly developing nation states. Recent studies attest to a ‘cultural divide’ that occurs when pedagogies reflect the dominant culture and policy environment and students’ own cultural perspectives are ignored, misunderstood or undervalued (Hatherley-Green, 2012). This paper critically analyses the application of theoretical perspectives to the development and implementation of elements of an actual graduate leadership program in an intercultural context in a middle eastern tertiary institution. The authors brought a significant level of intercultural competence to their work and aimed to approach leadership development in a way that would allow graduates to critically analyse and use leadership practices that were appropriate and just in their own social and cultural context. Thus the planning of the courses was informed by McLoughlin’s (2001) view that dimensions of task design, communication channels and structuring of information must be closely aligned to the cultural needs of learners. The pedagogical approaches evolved from a social-constructivist perspective exemplified in Lave and Wenger’s (1991) view of learning as an active and collaborative social phenomenon, and the content drew from both western and Arabic and Islamic research and literature. The program was based on a Habermasian perspective where it was important for the students to engage in critical conversations and discussions to compare and contrast ideas and to adapt them to their own leadership context. Both the nature of the dialogue, what Habermas (1984) termed ‘communicative action’ between the western teachers and Emirati students, and the affective aspects of the learning context were important here. The second section of the paper reviews the successes and challenges of the graduate program and draws on theoretical views of cultural difference, intercultural education, and Habermas’s concept of communicative action, to examine the ‘fit’ between theory and pedagogical practice in an intercultural leadership development context.