Professional preparatory health programmes generally involve clinical placements with a focus on integration of theory into real life practice. Reflective writing is often included in the assessment requirements for clinical placement courses. However enabling students to engage in deeper levels of reflective writing in action, on action and for action requires careful scaffolding and assessment task design within university clinical placement handbooks. The purpose of this case study was to explore iterative refinement of assessment exercises within clinical placement handbook activities. Specifically, the study examined students' responses to counselling experiences in authentic pharmacy practice, with comparative analysis undertaken for the various versions of the assessment task. Results showed that provision of iteratively developed guidelines, provided to three different groups of students, to support students in the assessment task, increased the marks achieved for individual components of the assessment. The results provide insight into how the design of these types of assessment exercises can be improved. (Contains 1 figure and 2 tables.)