The current study examines the empowering effects of transformational leaders and the extent to which these effects differ across mechanistic–organic organizational contexts. Psychological empowerment is hypothesized to provide a comprehensive motivational mechanism explaining the relationships between transformational leadership and employee job-related behaviors. In addition, the relationships between transformational leadership, employee psychological empowerment, and job-related behaviors are hypothesized to be stronger in organizations with more organic as opposed to mechanistic structures. Results based on a cross-organizational sample of employees and their immediate supervisors provide support for the hypothesized relationships. Psychological empowerment mediated relationships between transformational leadership and employee task performance and organizational citizenship behaviors. The mediating role of psychological empowerment was then found to be conditional upon mechanistic–organic contexts. More specifically, organic structures enhanced, whereas mechanistic structures constrained, the empowering influence of transformational leaders. In highly mechanistic contexts, the indirect effects were no longer statistically significant. Implications for theory, research, and organizational management are discussed. Copyright © 2013 John Wiley & Sons, Ltd.