Journal of Systemic Therapies 29(2): 26-45 Systemic training involves a tension between purpose (to promote trainees’ creative adaptability in specific situations) and responsibilities (to instruct, evaluate, and credential trainees who demonstrated acceptable levels of learning). In this paper, we describe some ways in which we have thought about and developed specific ways of dealing constructively with this tension while working in a multi-year systemic training program whose participants are practitioners from multiple sectors of society. Our contribution to this literature includes integrating concepts drawn from communication theory, adult development, and transformational learning. In the course of this project, we moved from seeing the systemic trainer as caught in a dilemma to a more productive conceptualization of a decision-tree including the experience of the trainees; situational features of time, context, and sequence; and specific patterns of conversation between trainers and trainees. In our work, we invite learning by inviting trainees to make three movements in the development of their own competence; our side of this process includes evaluating, responding and expanding. We describe the experience of our work with three students as examples of these movements and the ways they create possibilities for using constructively the paradox between our purpose and roles.