This experimental study was designed to investigate whether supervision meetings, in which students receive specific advice on how to use a development portfolio to monitor their progress and plan their future learning, helps them to develop self-directed learning skills and improve their learning in the domain. In the first year of a hairdressing program in vocational education, supervision meetings were used to provide students with either specific advice or not. Students in the advice group (n = 21) formulated better learning needs, selected more suitable learning tasks, completed more practical assignments, and acquired more certificates than students in the feedback-only group (n = 22). Interviews also showed that students in the advice group appreciated the supervision meeting more and perceived them as more effective than students in the feedback-only group. Guidelines are provided for the use of development portfolios and the organization of supervision meetings in on-demand vocational education.