Educational leadership has long been a focus of research and scholarship that focuses on effective education and school improvement. This has usually centred on the important practices of principals; but here we focus on the leading of those who are closer to the classroom—middle leaders. Middle leaders are those who have an acknowledged leadership position, but are also involved in teaching in the classroom. In this landscape, a prime role of middle leading is site-based staff and curriculum development. In this chapter, we discuss the features, characteristics and issues associated with leading from the middle, and we show how this is a mediated practice that is critical to educational development in school sites. It is mediated since the work of the middle leader is enabled and constrained by the cultural-discursive , material -economic and social-political arrangements exuding from policy and school personnel that are brought to bear on their practices. To navigate these arrangements, we will argue that the complex relational nature of this role demands practical wisdom, and the enactment of praxis.