A predominant understanding in information systems research is that technology has institutionalizing and social-izing effects in its interaction with humans in the human enterprise. This understanding no longer gives a full ac-count of the dynamics in the current workplace. Through a critical realist approach, the socio-technical mecha-nisms in the 21st century global enterprise is re-explored, through a study of 18 user’s productive behavior afford-ed by Unified Communication and Collaboration (UCC). The study finds that the mechanism of individualization is the cause of events that profoundly change the socio-technical reality. Individualization affects how people re-late to one-another and reduces the influence of the organization as a system. The power of individualization cre-ates a new parallel structure of small networks of close colleagues. The study shows the dialectic nature of mecha-nisms in a socio-technical system and provides a social system perspective of the dynamic individualization forces that now inhabit the self-organization of a complex socio-technical system.