Researcher roles as insiders and outsiders are important in qualitative studies. Yet, the roles and perspectives of insider and outsider researchers working collaboratively in transnational learning contexts have received little research attention. This paper reports on a small-scale qualitative project that explored our research collaboration as insiders and outsiders. We investigated three undergraduate Chinese international pre-service teachers’ academic experiences in one Australian university. The doctoral student researcher, as an insider who shared language and culture with the participants, undertook in-class observations and semi-structured interviews with the three participants while the outsider researchers developed and guided the overall project. In the course of data analysis, and using a reflexive lens, we were given insight into how our distinct cultural and linguistic identities and positionings steered our interpretations and enriched them as we made sense of them. In so doing we became aware of the ways in which our research plans and our own roles and dispositions were dynamically shaped and shifted as we worked with our participants and with each other. In this way, our research plan itself was changed while the process of interpreting the data became enriched and inspired confidence.