This paper explores the cumulative reflections of lecturers examining their tacit assumptions of teaching practice. Despite extensive literature on the educational value of reflection, there is less visible research on teachers assessing their own reflective thinking. This longitudinal interpretive study uses Larrivee’s assessment framework with a purposive sample of UK business students. Findings reveal insights for teaching reflection; acknowledging the discomfort of reflexive practice encourages learners to experiment with knowledge interpretation. The students’ struggle to engage in reflection resonated with lecturers’ parallel difficulties. The teaching approach balances deliberate structure with uncertain outcomes to trigger fresh interpretation of developmental theory and workplace relevance. Practice implications for lecturers are that harnessing uncertainty can provoke deeper insights that enable students to direct their learning and develop reflective skills. This case study offers a practical assessment example to enrich reflexive teaching, with scope to compare and replicate in different disciplinary settings.