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This qualitative study aims to investigate the competencies and effectiveness of humor use in workplace leadership. By exploring the elements underlying successful and unsuccessful humor use, this research offers insights into the competencies required for leaders to leverage humor effectively. Adopting a qualitative inductive approach, fifteen individual semi-structured interviews were conducted, generating a dataset of 51 critical incidents of humor use. Reflexive thematic analysis was employed to identify key themes, resulting in the identification of five central elements: Reading the context, Intention and motivation, Judgement and decision, Skillful delivery, and Understanding reactions. These elements provide a comprehensive framework for understanding humor use in the context of workplace leadership, emphasizing the importance of cognitive and emotional intelligence / competencies. The study proposes a theoretical framework based on these findings, providing the foundation of a new paradigm for understanding and measuring humor use. This research contributes to a deeper understanding of the competencies and complexities involved in using humor as a leadership tool and provides practical implications for leaders aiming to enhance their leadership effectiveness through humor.