This study is set in the rapidly changing higher educational environment that has ensued in Serbia and Montenegro in the post Milosevic era. Its primary focus is a "Training Trainers" initiative, mounted by the GTZ (Deutsche Gesellschaft fur Technische Zusammenarbeit/Society for Technical Co-operation), designed to upgrade the teaching capacity of academic representatives from four Serbian Higher Business Schools (HBS) in modern business and management education as part of a broader European project to foster democratic citizenship and to spur the political rehabilitation of Serbia. As a consultant employed by the GTZ to deliver a module in Human Resource Management (HRM) I was able to gain first hand insights into problems and issues associated with the assimilation and teaching of new business ideas by local experts. The article draws upon hermeneutic insight in order to understand the potential for misinterpretation and misunderstanding in intercultural educational dialogue in a particularly troubled economic, political and institutional climate. Although the module was perceived as being successful in it own right, institutional inertia in the field of education, cultural dissonance amongst primary stakeholders and an ethnocentric approach to programme formulation impeded the diffusion of new business knowledge into wider Serbian industrial structures. It is concluded that, in future, such initiatives would need to be more finely tuned to local circumstances and founded upon genuine dialogue between international educational actors.