Work placements and workplace learning are increasingly integral components of undergraduate degrees, run within post-compulsory educational institutions; both in universities and further education colleges in the United Kingdom (UK). The intent in workplace learning is to help students attain the work-ready competencies (or employability) sought by graduate employers. By consequence, the UK’s Higher Education (HE) and Further Education (FE) sectors are under pressure to identify and respond to students’ needs during this important, but often challenging transition to workplace learning. Conceptual considerations around work placements, drawing from employer and students’ perspectives on the challenges of placements are presented. This analysis contributes to discussions on students’ preparation and transition into work contexts, focusing on promoting self-regulation, as part of developing students’ capacities for this kind of independent learning and in building students’ pre-professional identities. The design of an outline ‘pedagogical pattern’ for scaffolding transition into work placements is provided, as a systematic approach to scaffolding students during transition and to aid workplace learning. Significantly, the pattern articulates the contemporary challenges associated with student support and self-regulation in commencing workplace learning, while recommending a flexible web-based solution that is informed by authentic student perceptions of placement support needs.