Acknowledging the accountability context in which many professionals work, the situation of one person observing the practice of another has educative potential. How might the observer help the observed to learn, and to learn how to learn, and vice versa? This study is about how a course tutor's visits to qualified teachers' classrooms, as a resource to the improvement of their teaching, was examined. Seeking to maximise the educative potential, the tutor's view of his own practice was jolted by some teachers' views about the judgemental dimension of his stance. Reflecting on this as a pivotal course experience, the tutor uncovered some assumptions and biases in his approach to his use of specialist knowledge and the educative purposes in mind. These were tested and developed by investigating how teachers had reacted to specific actions by the tutor in which his use of specialist knowledge had been guided by the intention to encourage the development of their professional autonomy. Reflection on the tutor's problem was about how to combine transmission with counselling of a Rogerian kind in his practice and it uses the distinction between espoused theory and theory-in-use. The study shows how personally new complexities in understanding and in practice of this situation emerged interdependently. These insights are offered as a projective model for an observer trying to harmonise intentions to give advice, evaluation, specialist knowledge and support to reflective learning, whilst seeking to learn reflectively from such experience. As part of this model, there are also some thoughts about the kinds of learning and knowledge involved, together with speculations and questions about understanding these things better.