This paper is about a narrative Cultural Historical Activity System exploration to support the transformation of individuals as they shift from training to an academic development paradigm is presented. The interaction with a group of educational consultants in the design, development and delivery of an academic professional development workshop is explored. A number of tertiary contradictions arose during the processes that included dialogical, double-stimulation, and experiential learning approaches. The contradictions were related to disciplinary concerns, staff technical skills (deficit), application of abstract educational theory (performativity) and an emphasis on outcomes and not tool-mediated knowledge construction. In this study the expansive learning cycle not only provided a framework for the exploration, but predicted the outcomes. However, the abstract notions of tool mediation, which are fundamental to the approach, require deeper exploration.