In attempting to understand the reasons for change failure it has been argued that research has generally been inadequate in addressing the broader contextual factors involved in the change process. In order to focus on these it is important to understand that leaders working on change implementation need to recognize that they act within a complex organizational system. Failure to recognize this can result in ‘stuckness’. However, leaders not only fail in change implementation through their lack of knowledge on systemic issues, but, in some cases, either unconsciously or consciously reinforce the systemic patterns that cause the organization to remain stuck and thus impair the implementation of the change. This article presents the results of a study based on interviews with leaders from 33 organizations who were each asked to recount two stories of organizational change that they had been involved with in a leadership role. Analyses of the data indicated that the leaders' ‘blindness’ to organizational systems and/or a focus on their own ego needs led them into a range of ‘traps’ that seriously damaged the success of change interventions. Leaders who were involved in successful change efforts, and avoided these ‘traps’, displayed a range of behaviors that demonstrated high levels of self-awareness, an ability to ‘work in the moment’, and an ability to remain in tune with the overall purpose of the change.