The purpose of this study was to identify the competencies hospitality unit leaders perceived to be most critical for career development, and to determine whether perceptions of the importance of various skills and attributes/abilities varied when leaders worked in different organizational contexts. Leaders from two hospitality segments, land-based hotels and ocean-based cruise ships, participated in the study. Findings indicated notable differences between the two samples on a number of items. A background of relevant research on hospitality leadership competencies is provided. Contextual variables are examined as they contribute to better understanding differences in perceived competency requirements between land-based and ship-based leaders. Four contextual dimensions (staff composition, task requirements, organizational structure, and the external environment) are explored. A conceptual model is presented that illustrates the posited influence of organizational context on hotel and ship leadership competencies as they impact both selection processes and development activities. Results of this opinion-based study suggest that, while senior hotel and ship practitioners share a need for certain core competencies (positive attitude and effective listening), organizational context likely influences the relative importance of specific skills and attributes/ abilities required for effective leadership in each industry segment. Findings support previous research and have implications for educators, practitioners, and researchers.