This paper presents a cautious argument for re-thinking both the nature and the centrality of the one-to-one teacher/student relationship in contemporary pedagogy. A case is made that learning in and for our times requires us to broaden our understanding of pedagogical relations beyond the singularity of the teacher/student binary and to promote the connected teacher as better placed to lead learning for these times. The argument proceeds in three parts: first, a characterization of our times as defined increasingly by the digital knowledge explosion of Big Data; second, a re-thinking of the nature of pedagogical relationships in the context of Big Data; and third, an account of the ways in which leaders can support their teachers to become more effective in leading learning by being more closely connected to their professional colleagues.