This article provides two 'portraits' of headteachers in primary schools in England and Hong Kong, derived from semi-structured interviews with these individuals. Contrary to some claims that such a small sample is worthless, this article argues that what is most meaningful is sometimes derived from the singular and unique; that generalisations in education are as likely to be useful if they are 'fuzzy' generalisations as if they are from scientific or statistical generalisations; and that the individual case can strip away the clutter of large contexts and allow recognition of a common shared humanity. What these portraits also show is that responses to larger contexts are heavily dependent on personality and local context, and that if policy implementation and professional development are to have impact, then an attention to the personal and the local are going to be critical factors in any success in these areas[Copyright of Education 3-13 is the property of Routledge. Full article may be available at the publisher's website: http://dx.doi.org/10.1080/03004270701577347]