This article explores two case colleges in England to consider how context, conceptualisation, orientation and action interact in relation to diversity issues in leadership. Focus group and individual interview data are analysed. Context is perceived as influential in shaping concepts and action. In one case, the diversity and socio-economic disadvantage of the community create a perceived imperative to address diversity, resulting in multiple conceptions of diversity and systemic action. In the second case, the context of a perceived homogeneous community interacts with an equal opportunities conceptualization of diversity to justify little or no action. A tentative theoretical model is suggested to frame further enquiry.