The interpretive grounded theory (GT) study analyses information system (IS) enabled organizational change in two private sector organizations. These two organizations, who are long term partners, were developing a new IS product to divergent markets. The data was gathered through 15 interviews, conducted at the phase of initial rollouts. The findings focus on the results of the theoretical coding phase in which selective codes, referred to as change management activities, are related to each other. As a theoretical contribution, the dynamic structure presents how the change management activities appear differently, depending on a set of choices. Several paradoxical situations stemmed from inconsistencies and/or tensions, because the choices did not support the targeted change management activities. The study thus proposes that there is an increasing demand to analyze the sources of paradoxical situations. Paradoxical situations in these five opposing forces were identified: long term vs. short term, macro vs. micro, past vs. future, centralized vs. distributed, and control vs. trust/self-organization. Some paradoxical situations arose because of the nature of the trust-based IS partnership, while others were socially constructed as a result of unintended consequences of actions in relation to the strategic goals. Managerial efforts are increasingly required for identifying paradoxical situations at an early stage and for considering the right balance for the opposing forces in the dynamic IS change process.