Education has moved from teacher to student-centred practices. Increasing emphasis is placed on ‘life-long’ learning in the context of a rapidly changing knowledge base. Self-evaluation is seen as one strategy to facilitate student-centred continuous professional development. The literature, however, suggests that learners’ ability to self-assess is mixed, and little is known regarding how students perform self-assessment. This study focussed on senior nurses undertaking a scenario-based clinical skills course. Learners were asked to self-evaluate several times during the course. This research explored the influences on using the self-evaluation exercise. The study drew upon grounded theory methodology and was influenced by constructionist and postmodernist theories. Three methods of data collection were used: semi-structured interviews, observation of supervision sessions and recording of the numerical self-evaluation ratings. Multiple interviews with students (n = 14) and the educational supervisor (n = 1) were conducted. Thematic analysis and data collection were conducted iteratively. The study found that feeling confident and stating that confidence were not necessarily the same. Feeling confident was complex, influenced by changing perceptions of clinical skills and credibility. Changing frames of reference were used to judge feelings of confidence. Stating confidence appeared to be socially negotiated, influenced by social acceptability considerations such as modesty and the need to show progress over time. The discourses of empowerment and surveillance were influential and self-evaluation is discussed using Foucault’s theory of governmentality, illustrating how learners can be both empowered and controlled through self-evaluation. Further consideration of the socially constructed nature of self-evaluations would benefit both educational practice and future research.