How research is interpreted and imparted remains an ongoing challenge for researchers. We use the theory of practice architecture therefore to treat issues of research design, interpretation and writing of the findings. In so doing, we take the position that to understand how principals learn to lead, researchers must take into consideration the importance of context -– that is, the historical, cultural, material and relational aspects of that space and how these facets frame the processes by which primary school principals in Trinidad and Tobago learn to lead. This theoretically infused approach to understanding leadership practices not only highlights the tensions, traditions and power structures therein but also the ways in which these inherent complexities and contradictions can now be communicated through research. In representing practice landscape as a challenge of context, we therefore privilege and situate the stories of how principals negotiate the relative importance of age, experience, gender, authority and cultural legitimacy as critical aspects of their socialisation and learning experience. Implications for how researchers can re-position and re-interrogate notions of insider and outsider research are also discussed.