The evidence linking self-monitoring (Snyder, 1974) and leadership suggests that it is better to be high than low in self-monitoring regarding leader effectiveness (Day et al., 2002); however, social responsiveness could be a double-edged sword when it comes to leading organization change. It was hypothesized that high self-monitoring (HSM) leaders would launch change in a participative manner and create positive conditions for change, but they would lack strength of purpose for leading the effort in the face of resistance. Grit (Duckworth, Peterson, Matthews & Kelly, 2007), an individual characteristic introduced recently by positive psychologists, is potentially a positive characteristic of change leaders. It was also predicted that grit would be a positive predictor of leader strength of purpose for leading change. Drawing on these literatures, a theoretical model was developed and tested to examine the interaction effect of these two characteristics and a change leader's situation (resistance or support) on strength of purpose (commitment to change goals and intentions to stay with the organization). Two surveys, one scenario-based and one experience-based, were administered to senior leaders (mean age = 43) from across the globe representing a wide range of industries and job functions. The results provided some support that self-monitoring interacted with the leader situation to predict leader approach to change in the scenario survey group, but not in the experience survey group. The findings also demonstrated support for self-monitoring theory in that cultural context moderated the relationship between self-monitoring and leader approach to change, such that HSMs' approach varied significantly depending on whether they were leading change inside or outside their own country of origin (i.e., nationality) whereas LSMs did not vary their approach across these different contexts. The prediction that grit would predict leader strength of purpose was unsupported. It was also found that cultural context moderated the relationship between leader situation and intentions to stay with the organization such that, in conditions of less support (i.e., resistance) from one's established in-group (nationality or societal culture match between the leader and change recipients), leaders expressed higher intentions to leave than when unsupported in out-group conditions. These results and the implications for future research and practice are discussed.