A social issue that has affected the value of information systems implementations in organizations is resistance to change. While a great deal is known about the ways in which people interact with each other and affect the use, and implementation of information technology, the use of collaboration technologies in assessing the outcomes of organizational processes is still in its formative stages. This paper investigates the use of a Group Support System (GSS) in assessing the level of resistance to change among employees of a top four consulting company going through an acquisition of its major businesses. Senior, executive, to middle management level employees of this firm were conducting a game designed to help then in understanding and managing change. This Change Challenge Game was conducted through role playing of decision makers whose aim is to arrive at mutually agreeable outcomes. Following an analysis of the GSS from seven sessions comprising five different roles, this paper provides insight into the types of resistance to change encountered per role. The contribution of this paper is in the framework that maps categories of resistance to change with the roles encountered organizations of this type.