While the notion of being “lonely at the top” is well-known, leader loneliness remains an underexplored phenomenon in organizational research. Drawing on feelings-as-information theory, this study develops a dual-pathway model to investigate how leader workplace loneliness influences their interpersonal behaviors toward followers. We propose that leader workplace loneliness activates two distinct mechanisms: a maladaptive self-dehumanization pathway that drives counterproductive work behaviors (CWB) toward employees, and an adaptive need-to-belong pathway that fosters organizational citizenship behaviors (OCB) directed at employees. Furthermore, we argue that the team communication context moderates these pathways: team communication adequacy amplifies adaptive responses while attenuating maladaptive ones. Using multi-source and multi-wave field data, our findings reveal that high team communication adequacy weakens the relationship between leader workplace loneliness and self-dehumanization but does not significantly affect the link between workplace loneliness and the need to belong. These findings underscore the asymmetric role of communication adequacy in shaping leader responses to workplace loneliness. This study contributes to the literature by elucidating the dual interpersonal consequences of leader workplace loneliness and identifying the contextual conditions under which loneliness can either undermine or enhance workplace relationships. Practical implications for leadership development and organizational communication strategies are discussed.