Those involved in any learning situation whether as educators or as students, come to their tasks enmeshed in the contexts which form part of their wider environment. Hence they are both knowingly and unknowingly influenced by the web of conflicts, dilemmas and power differentials which are part of their system of origin. In this chapter we, the authors, recall an experience of a course where the four key players - the students, their lecturers and their respective organisations - did not share the same learning goals. The chapter examines from our perspective, the impact these differences had on classroom dynamics and highlights the need to take account of the prevailing values and circumstances in the broader environments that impinge on adult students and on their educators. Our exploration of the experience incorporated three distinct but interconnected processes. We sought (i) to construct a narrative of events; (ii) to reveal the non-conscious processes through which we filtered our experiences; and (iii) to attend to the systemic dynamics that formed the framework for interaction among the different players involved. We recognise that our reality is no more privileged than that of any of the other parties (Usher and Edwards, 1994) and therefore we recounted the events more as witnesses than as holders of the ultimate truth of what happened. Our goal was to record only our 'truth' at a particular time, recognising that this has probably changed and evolved over the years since the course was delivered, and that it is but one of a range of possible perspectives (Kenny and Gardner, 1989). We have afforded ourselves this position of 'knowing subjects' in order to further our own learning and in so doing to create useful knowledge for use in the future. We are also aware that the meanings and understandings generated by our enquiry, cannot be divorced from our subjectivity. Our approach to the topic is not that of impartial investigators. On the contrary we were active participants in the events and undertook this reflective process with the express purpose of learning how to do our job better.