Becoming a doctor involves a series of transitions that require medical students to be equipped with the appropriate knowledge, skills, confidence and professional approach at each step. This pilot cross-sectional study canvassed five cohorts immediately after completing Years 1-5 in a five-year undergraduate medical program (Gold Coast, Australia) regarding their preparedness for the next year. The survey, an amalgamation of two validated inventories, was tailored for each year group to include the expected competencies in five areas. Despite a low response, those who did participate provided valuable information regarding their competence and confidence in terms of their interpersonal and intrapersonal skills, their clinical skills, their ability to apply their theoretical knowledge and investigations. Time management and balancing work and their studies were some areas in which support might be needed. Generally, all student felt comfortable with the communication and physical examination skills but up to half of some of the more senior students were not confident towards dealing with a violent patient and about 20% did not feel at ease communicating and assessing a patient with a mental health issue. Students identified two other areas that requiring curriculum interventions: Working with patients who might be using non-allopathic medications and calculating drug doses. As both impact on patient outcomes, a follow-up study is required. Different recruitment strategies need to be investigated.