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Although it is clear that leadership plays a significant role in followers’ psychological health, the specific mechanisms by which leadership effects may take place await further theorizing and investigation. We argue that communication practices may constitute such specific mechanisms. Therefore, the purpose of this study is to examine how supervisor-subordinate conversational richness and communication frequency are associated with subordinates’ perception of work role stressors. Through an online survey, the study found that supervisor-subordinate conversational richness has a significant predictive effect on work role ambiguity. However, supervisor-subordinate conversational richness interacts with communication frequency in their effects on role conflict and role overload. These findings contribute to theories of leadership communication and the continuous development of role dynamics theory.