This paper documents an ongoing collaborative project to develop a situated and culturally sensitive mobile application to assess the educational quality of youth-related initiatives in 38 municipalities of the border regions of Portugal. We focus on sharing the narrative of our cross-disciplinary experiences, drawing on reflexive notes written by team members over 1 year. This accountability process relating to interactions, expectations, and negotiations was analysed using the interdisciplinary theories from education and knowledge work. The outcomes of this interdisciplinary work, which is focussed on product development, are filled with unique challenges shaped by distinct disciplinary fields and scientific "habitus." Relational encounters have followed conflicting understandings (around concepts), which took place in parallel with the progressive redesign of the initial plans and expectations. This brought unexpected results, such as learning opportunities and the development of a common ground, indicating that an exercise of reflexive positionality is fundamental for interdisciplinary collaborative endeavours.