Educational developers are engaged in identifying and resolving tensions in their working roles that are often portrayed as multi-faceted and ambiguous. Similar uncertainties exist when individuals undertake research as insider members of the communities that are the subject of their research. They also experience significant ambiguity around their role that has an impact both on the research process and on their own identity. This paper proposes that there is much to be learnt from this experience that may help to explain ambiguities in the educational developer's position, both in their working roles and when undertaking their own research. In this paper, I explore my own experiences of being an educational developer and insider researcher and discuss the dilemmas that arose, with the aim of enabling others to reflect on their own positions and understand the insights, risks and opportunities presented by insider research.