The phrase transferable skills describes skills applicable across diverse contexts, especially within the workplace. However, the literal interpretation of skill transfer is often unclear to students. While educators assume skills acquired in one setting (university) can seamlessly transfer to others (the workplace), reports persist in a skills gap, suggesting graduates lack transferable skills and/or the confidence to apply them in novel situations. Addressing this requires an approach that empowers students to align the skills they have developed via life experiences with their professional identity. Traditional assessments are not best suited to capturing complex competencies, including employability, in a form that can be effectively evaluated. Students’ ability to transfer their skills is more likely with learner-centred strategies that frame unfamiliar situations as learning opportunities. One solution is using portfolios centred on active reflection to help students evidence capabilities and develop a longitudinal view of their experiences aligned with their professional identity. For final-year students transitioning to the workplace via placements, portfolio assessments can build confidence to transfer academic skills to practical applications. This chapter showcases portfolio assessment embedded in three placement courses and a co-curricular program in the STEM disciplines, demonstrating how evidence-based articulation of skills through reflection enables valuable skill transfer to unfamiliar contexts.