With this paper, we contribute to the complex field of assessment of student learning in work placements. The complexity includes the dual role of clinical educators as mentors and assessors, students as pre-accredited practitioners and the diverse purposes of assessment. A philosophical hermeneutic approach was adopted to explore the perceptions and practices of clinical assessments as they were experienced by clinical educators and students of the Bachelor of Physiotherapy programme of the Claudiana College of Health Professions at Bozen, Italy. Philosophical hermeneutics is grounded in dialogues where dialogue partners explore each others' statements or experiences, question assumptions that underpin experiences and perceptions and search for shared understanding. Focus group questions invited participants to share their experiences and engage in a dialogue with other participants. The research team engaged in cycles of interpretive dialogues according to the hermeneutic tradition. Data interpretation was guided by interpretive questions such as: what does the transcript say about assessment? Each target group was analysed separately before comparing them. Findings highlight that the relational and emotional dimensions of assessment experiences were key issues for both target groups. Finally, conclusions are drawn from our findings in form of recommendations for placement assessment practices as well as for future research.