This article presents initial findings from a case study of the challenges facing newly appointed middle leaders in an independent school in the North West of England. The research approach has included interviews with twenty-five staff from within the school. It was observed that the skills set needed for middle leadership is different to that of the classroom teacher. The challenges faced by the middle leader come from a variety of sources which appear to lie largely outside the middle leaders' control. However, there are also several factors that do lie within the middle leaders' sphere of influence and which enable them to deal with and overcome the challenges they face. Linking this to international research into skills acquisition, it is concluded that for the newly appointed and inexperienced middle leader there are specific and identifiable factors that can be prioritised for development, and that more focussed approaches of leadership development should be adopted.