Transitions within medical, veterinarian, and other health professional training, from classroom to workplace, between undergraduate, postgraduate, fellowship phases, and to unsupervised clinical practice, are often stressful. Endeavors to alleviate inadequate connections between phases have typically focused on preparation of learners for a next phase. Yet, while some of these efforts show results, they cannot obliviate transitional gaps. If reformulated as ‘not completely ready to assume the expected responsibilities in the next phase’, transitions may reflect intrinsic problems in a training trajectory. Indeed, the nature of classroom teaching and even skills training for example, will never fully reflect the true context of clinical training. In various stages of clinical training, the supervision provided to trainees, particularly medical residents, has increased over the past decades. This addresses calls for enhanced patient safety, but may inadequately prepare trainees for unsupervised practice. Transitions often evolve around the question how much support or supervision incoming trainees or junior professionals require. We propose to consider receiving incoming trainees and new employees in clinical workplaces with a conversation about required supervision for discrete tasks, or entrustable professional activities (EPAs). EPAs lend themselves for the question: “At what level of supervision will you be able to carry out this task?”. This question can be answered by both the trainee or junior employee and the supervisor or employer and can lead to agreement about specified supervision for a defined period of time. We expect that this “supported autonomy tool” could alleviate stress and enhance continued development after transitions.