This paper presents research findings on practitioners working with young people on Entry to Employment (E2E) programmes in the north of England. E2E continues a long tradition of work‐related learning for unemployed school leavers for whom other forms of education or training are deemed unsuitable, and is part of the UK government’s strategy for reducing the numbers of young people not in education, employment or training (NEET). The paper explores the biographies of tutors and their routes into E2E teaching. It also discusses the training and development they have experienced, in the light of the expansive–restrictive continuum of workforce development introduced by Fuller and Unwin. By analysing the dispositions, interpretations and actions of practitioners and relating them to wider policy discourses, the paper also examines the learning culture of E2E. It argues that, although they demonstrate significant levels of care, enthusiasm and teaching ability, practitioners operate within a largely restrictive approach to workforce development and learning. The paper concludes that both practitioners and learners would benefit from a re‐evaluation of the material and discursive relations under which E2E operates.