Management research has been challenged by the altering realities of organization life, job roles, and individual motivations that have long guided traditional theoretical thinking. The classical frameworks regarding managerial performance requirements have been largely based upon organizationally driven underpinnings. We propose a cognitive shift suggesting that individually driven roles and desires are impacting the relevancy of conventional job requirements. Our study analyzes the utilization of managerial skills, mindsets, and roles as perceived by 259 executives representing nine industries and ~200 organizations. The results reveal that the interpretation and application of managerial roles are primarily influenced by the individual’s intentions rather than adherence to the current organizationally based theoretical taxonomy as taught by many business schools. These findings illuminate the gap between the vast amount of effort researchers and educators have expended on taxonomic precision and its questionable relationship to organizational and individual learning and effectiveness. The theoretical and practical implications of these findings are discussed along with recommendations to extend the current research.