Increasingly designers from an array of different disciplinary backgrounds work in international and community development, yet design education rarely prepares them for the challenges and roles in this context. The article reflects on issues of power and representation during design research in The Gambia by adapting reflexivity and positionality which are key concepts established in development studies. Reflections are based on research carried out in The Gambia since 2010 which is comprised of phases of immersion, mapping and co-design. They provide in-depth insights currently lacking in design literature that demonstrate the value of reflexivity and positionality to iterate roles and methods in community-based design. Whilst not suggesting particular teaching methods, the article proposes the integration of these concepts into existing structures to better prepare students for increasingly common futures in the workplace. Broader themes that emerge and can be adapted to different design contexts include building trust, entanglement in power dynamics between different actors, personal vulnerability, as well as the need to challenge problems as starting points for design interventions.