When students graduate, they cannot rely on educators telling them if their work is good enough. To do so, they need well-developed evaluative judgement, the capability to make decisions about the quality of their own and the work of others. There is little evidence about the specific approaches that can develop evaluative judgement--or how to study those approaches. Understanding how to research evaluative judgement in the context of pedagogical activities is essential to advance both research and practice. This paper explores how to research evaluative judgement within the context of a longitudinal reflective diary kept by first-year students in a built environment course. Students were required to observe construction and managerial processes on worksites and record these in their reflective diaries. Thematic analysis was conducted on a dataset comprising approximately 290 pages of text. Our analysis suggests it is possible to observe students' evaluative judgement even in some tasks that are not specifically designed to evidence it. Recommendations are made about improving the design and implementation of assessment tasks with the inclusion of reflective practices and dialogue as key enablers of the development and therefore research of evaluative judgement.