The present research sought to examine when and why transformational and transactional leadership are perceived by followers to be effective. A series of five studies revealed that perceived effectiveness of transformational and transactional leadership is influenced by the fit between leadership style‐driven encouraged strategies and followers' preferred strategies. Specifically, we found that transformational leadership primarily encourages promotion‐focused strategies and, accordingly, creates a regulatory fit for promotion‐focused followers. In contrast, transactional leadership primarily encourages prevention‐focused strategies, creating a regulatory fit for prevention‐focused followers. As a consequence of this regulatory fit, leadership is perceived as more effective and predictive of enhanced effort. By integrating literature on self‐regulation with insights from leadership research, this research contributes to a deeper understanding of the leadership process and of interpersonal influences on self‐regulatory experiences. Copyright © 2014 John Wiley & Sons, Ltd.