To maintain team learning for assistants in preschools, dialogue and group discussions are important. These dialogues and discussions can happen both as a part of spontaneous supervision and as a part of an organized process of supervision. Bakhtinian theory of understanding and its notion of dialogue could be used to organize supervision of preschool assistants in Norway. In this study, the goal is to investigate how assistants in preschools in Norway experience supervision and explore how supervision practice could be organized through Bakhtinian ideas and the concepts of chronotopes and chronotopic thresholds. Pedagogical experiences that shift the thresholds of communication can provide a means of operating on the boundaries of meanings within pedagogical situations. These processes encompass reflection and transformation in understanding experiences. Surveys were completed by preschool assistants in 28 preschools and a series of interviews also conducted with administrative leaders, preschool teachers, and preschool assistants. The data indicated that assistants believe that opportunities for reflection and sharing of experiences with others at work would help them learn and become better professionals. It is important that preschool assistants are acknowledged and allowed to discuss their experiences and values. This, in turn, requires supervisors who are able to supervise from a holistic perspective.