Considering the potential impacts of context-specific value systems in individuals’ perceptions of phenomena, this study seeks to investigate whether and how cultural differences could influence the effectiveness of leadership styles in establishing trust and positive employee outcomes (PEOs) as well as the relationships between such outcomes based on the GLOBE project. The sample consisted of 1647 valid responses from 128 independent hotels’ employees in four countries from two GLOBE clusters (Anglo and South Asia). Multilevel structural equation modelling has been used for the analysis. Significant but different relationships were found between Servant Leadership and Transformational Leadership with Trust, and PEOs in the two clusters, which could be potentially attributed to societal and contextual factors as a deeper layer mechanism. Our findings have significant implications for both academics and hotel managers in terms of the critical role of alignment between context-specific contingencies and the selected leadership style in establishing trust and PEOs.