We explored the use of a video-based reflective design in preparing first-year pharmacy students for their Objective Structured Clinical Examination (OSCE) in Victoria, Australia. This involved pre-workshop activities (a recording of themselves simulating the pharmacist responding to a simple primary care problem, written reflection, review of the OSCE video examples and pre-workshop survey); workshop activities (peer feedback on videos) and post-workshop activities (summative MCQ quiz and post-workshop survey). These activities took place three weeks before their OSCE. A mixed-method study design was employed with quantitative and qualitative analyses of the surveys and a focus group. A total of 137 students (77.4%) completed the pre- and post-workshop surveys, and ten students participated in the focus group. More student participants (54%) reported feeling prepared for the OSCE post-workshop than pre-workshop (13%). The majority (92%) agreed that filming, watching and reflecting on their video allowed them to learn and improve on their skills for the OSCE. The regression analysis found that video recording submissions and written reflections correlated positively with student OSCE performances, and the video-based reflective design learning experience was perceived to be beneficial in multiple ways. Thematic analysis of the focus group data revealed that students acquired metacognitive skills through the self-assessment of their video recordings, developed an awareness of their learning and were able to identify learning strategies to prepare for their first OSCE. Fostering students’ feedback literacy could be considered in future educational designs.