Sound knowledge of the learning process and connectedness of assessment in higher education is imperative. Assessment is essential for both learners and teachers to ensure, and to provide evidence, that learning outcomes/objectives against set competency levels have been achieved for the chosen programme of the study. However, many coming into higher education are often unaware of the rules of the game. In this perspective, we will highlight the reasons why assessment is important, how assessment and feedback affect students’ learning process and why the process of assessment can often affect students’ mental well-being. We will appraise the different methods of assessment with a specific example (Objective Structured Clinical Examination, OSCE) and highlight why it is important that we adopt a holistic approach towards fostering assessment know-how and student well-being.