The Uganda Martyr’s University (UMU), with support from the Vrije Universiteit in Amsterdam (VU) and the University of Pretoria (UP) has initiated a project with one of its aims the development and implementation of a Masters degree in ICT Management at UMU. The project was initiated in 2007 and the first students enrolled in April 2010. VU facilitates the funding for the project whereas the role of the UP in this collaboration is to assist with the development and implementation of the Masters programme in ICT Management, with the focus on capacity building of the UMU staff. Although the project is still in its infancy, differences between assumptions and expectations of UP and UMU stakeholders are becoming apparent. Using the approach of participant observation and Critical System Heuristics as a conceptual framework, the authors critically reflect on the collaboration between UMU and UP. Results from the project initiation phases highlight the need for crafting a collaborative partnership which negotiates different views of quality and quality control and the issue of contextualised knowledge, keeping in mind the importance of an openness to unexpected outcomes and innovation. Results also highlight the importance of a sense of companionship, openness and trust, and ultimately the need to address power relationships in intercultural collaboration in Africa.