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Teacher Trainers are expected to analyze training requests in the context of continuing education for teachers, even though their usual activities consist of teaching courses and seminars. We seek to better understand what workplace learning is, and more precisely the nature of this kind of learning and how it is put into practice, as well as to enumerate the individual and situational elements that seem determinant in the observed changes. This article presents elements from two case studies bearing on the practices of two novice trainer-designers when they are involved in design work following a request for training made by a group of professionals. The results show that strong identity concerns are present when first setting out in training design.