In this paper, we examine workplace educators’ interpretations of their assessment practices. We draw on a critical practice lens to conceptualise assessment practice as a social, relational and situated practice that becomes critical through critique and emancipation. We conducted semi-structured interviews followed by roundtable discussions with physiotherapy clinical educators in the workplace. Employing a critical hermeneutic approach, data was scrutinised to understand relational and critical dimensions of assessment practices. Findings revealed that participants were socialised into assessment practices. They were aware of the challenges, and they grappled with the tension between their practice-based judgments and documentation of competence. Despite this tension, there was a reluctance to move their awareness of practice tensions towards emancipatory action which could relieve these tensions. We conclude that it is important to acknowledge the judgements which inform assessment practice and the tensions assessors feel between objective and subjective assessments. Assessors who deliberately engage with these tensions can emancipate their assessment practices towards a critical, wise and self-defining practice that nurtures lifelong learning in students and assessors alike.