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Transformational leaders inspire followers to perform beyond expectations and to become transformational leaders themselves. Research evidence shows that transformational leadership has positive effects on people, teams, organizations, and nations. In addition to producing higher levels of follower performance, transformational leadership results in increased follower satisfaction and commitment. However, there is still much to be learned about the complex set of antecedents that predict perceptions of transformational leader behaviors, and research is scarce regarding moderators that impact the relationship between leader behavior and follower outcomes. Most research regarding antecedents of transformational leadership has focused on leader personality and other individual differences, but there are other potential predictors not addressed in the literature, such as how the match between a leader and the situation influences transformational leadership. This study expanded upon previous research by examining the constructs of person-organization fit, person-job fit (demands-abilities and needs-supplies), and motivation to lead as predictors of transformational leader behavior. Because followers' fit with the situation may influence their receptiveness to transformational leadership, I also examined follower perceptions of person-supervisor fit and person-organization fit as moderators of the relationship between transformational leadership and follower outcomes. I hypothesized that these relationships would be stronger for those with higher levels of fit perceptions and recruited participants from multiple organizations to test the hypotheses. A sample of 215 leaders across 10 organizations provided self-report data regarding the proposed antecedents, as well as their personality characteristics, the need for change in their work unit, and the performance of their followers. Their supervisors provided ratings of leader effectiveness and assessed the need for change in the leader's work unit. A sample of 1,284 followers assessed the leaders' transformational leader behaviors and provided self-report data regarding the proposed fit moderators and their own work attitudes, which included job satisfaction and intentions to quit. Analytic strategies used to test the hypotheses were correlational analysis, multiple regression, hierarchical linear modeling, and moderated mediation. Initial regression results showed that both needs-supplies fit and demands-abilities fit were significantly related to transformational leadership. After control variables were taken into account, only demands-abilities fit remained significantly related to transformational leadership. Consistent with previous research, transformational leadership was related to boss ratings of leader effectiveness as well as to follower job satisfaction, intentions to quit (negative), and organizational citizenship behaviors (but not to task performance). Of the proposed moderators, support was found for the interaction of transformational leadership and person-supervisor fit influencing intentions to quit (intentions to quit was positively related to transformational leadership; the relationship was stronger for those with higher levels of person-supervisor fit), the interaction of transformational leadership and person-organization fit influencing intentions to quit (intentions to quit was negatively related to transformational leadership; the relationship was stronger for those with higher levels of person-organization fit), and also for the interaction of transformational leadership and person-organization fit influencing task performance (task performance was positively related to transformational leadership; the relationship was stronger for those with higher levels of person-organization fit). Theoretical and managerial implications are also discussed, along with limitations of the study and suggestions for future research.