Recent years have brought the private and non-profit sectors closer together in terms of cross-sectional collaborations. As businesses have become more involved in communities, initiatives such as employee volunteering (EV)—where employees are encouraged to volunteer by their employers—are becoming more popular and are receiving more scholarly attention. However, the question still remains as to whether the main reasons behind cooperation are related to strategy: does interaction and communication in EV mirror a more ideal- or strategic approach? As EV programmes (EVPs) bring together actors with different world-views and perspectives, much can be learned from studying their interaction. The present study examined the nature of communication in EV and whether this communication reflects a strategic (based on self-interest) or ideal (corresponding to Habermas’s ideal speech situation and stakeholder dialogue) approach. In addition, the study looked at factors that, according to participants, facilitate improved communication and understanding in EV. The findings indicate that communication in EVPs largely reflected the strategic approach. However, the ideal approach is still apparent in some situations and can successfully be used given the right conditions--for example, in situations of long-term collaboration with increased experience when participants invest time, resources and motivation in building relationships. Time and honesty was also important factors. However, a range of barriers made collaboration more difficult. Pursuit of strategic short-term solutions and shortage of resources and time may hinder important dialogue and understanding.