This paper challenges the generic single conceptual viewpoint that designers have of groupware and specifically Groupware Calendar Systems (GCS). From the analysis of interviews, we categorized different calendar usage and activity that distinguish between the ‘Private Calendar’, the ‘Public Calendar’ and the ‘Shared Calendars’. Based on this categorization, we identified the dynamic relationship found in scheduling activity. The rationale stems from the growing use of web-based technology as integrated web programs that are facilitating new and different forms of collative team working. The purpose of this paper is to explore the weakness found in the ‘current’ GCS, ‘Deterministic’ position, further we go on to articulate the basis of an alternative approach, ‘Social Technological Teamwork’. KEYWORDS Groupware, Groupware Calendar Systems, Social relationship, Social Negotiated Activity, User Requirements