The concept of empowering leadership has attracted the attention of both academics and practitioners because of its important role in enhancing employee performance. Although empirical evidence clearly demonstrates that empowering leadership can have a significant effect on positive managerial outcomes, there is a paucity of research on its antecedents and processes through which it influences work outcomes. Thus, this study suggests a comprehensive conceptual model of empowering leadership, mainly focusing on the trickle-down effects of across levels of hierarchy. Specifically, based on theories of social learning and social exchange, this study examines the influence of empowering leadership of second-level leaders on subordinates’ various work outcomes through first-level leaders’ empowering leadership to help identify mediating process that may underlie relationships between second-level leaders and subordinates’ outcomes. Additionally, in order to explore the social learning of empowering leadership in detail, this study focuses on the antecedents and processes of empowering leadership learning. Data were obtained from subordinate–supervisor dyads from the South Korean Army. The results of this study showed mediating effects of first-level leaders’ empowering leadership on the relationship between second-level leaders’ empowering leadership and subordinates’ task performance, organizational citizenship behaviors, and social loafing. These results support the trickle-down effects of empowering leadership on subordinates’ outcomes. Moreover, LLX mediates the relationship between second-level leaders’ empowering leadership and the first-level leaders’ empowering leadership, and this result supports the social learning of empowering leadership. Exchange ideology also moderated the social learning of empowering leadership, such that the relationship was stronger when exchange ideology was low rather than high. The results of this study have both theoretical and practical implications. Theoretically, this study provides empirical evidence to help determine whether second-level leaders’ empowering leadership facilitates first-level leaders’ empowering leadership. This study contributes to the literature by further examining the antecedents of empowering leadership by showing how relational, individual, and situational factors influence empowering leadership. This study also explains how empowering leadership can spread across multiple downward linkages by supporting the existence of “trickle-down effects” of empowering leadership. Practically, this study helps understand the importance of high-level leaders’ empowering leadership to facilitate their low-level leaders’ empowering leadership. This study also suggests the importance of relational, individual, and contextual factors to facilitate the social learning of empowering leadership. In conclusion, empowering leadership has a synergistic effect across leadership levels; therefore, top managers and high-level leaders should focus on training empowering leadership of field managers and leading by example to create a more empowering environment. However, this study has limitations, such as the use of cross-sectional analyses and perceptual data. Future research may seek to use longitudinal and objective measures.