To gain a critical understanding of the lived challenges within the managerial cycle (recruitment, employment, termination) in professional league football, the research initially followed a qualitative approach in the form of semi-structured interviews. A total of 16 professional league managers completed a face-to-face interview using open ended questions, allowing them to share their true perspectives (Dale, 1996). The interview schedule concerned the managers' perceptions of challenges faced within the role, strategies to deal with the challenges, specific skills and qualities possessed, and future challenges within the role. Data were analysed via deductive and inductive content analysis (Biddle, Markland, Gilbourne, Chatzisarantis, & Sparkes, 2001; Côté, Samela, & Russel, 1995), and emerging themes were subjected to member checking (Sparkes, 1998). The range of experiences revealed a number of proposals for how to deal with cultural, organisational and personal related challenges. The managers’ ability to delegate responsibilities and to adapt effectively to changing environments seemed critical to avoid loops of accumulating problems. Unprofessional attitudes to recruitment and sackings seemed embedded in the culture. The eagerness for short-term results was perceived as a threat to sustainability in managerial work currently and in the future. The managerial cycle model was developed on the basis of Study One findings. Study Two aimed to examine the managerial cycle model by bringing in the internal (senior management and support staff) and external (Norwegian Football Association, League Managers’ Associations) key stakeholder views on the training, development and support of managers within the various phases of the managerial cycle (recruitment, employment and termination). A total of 21 internal (n=18) and external (n=3) key stakeholders completed a semi-structured interview, which was analysed via both deductive and inductive content analysis. The findings gave insight in senior management experiences regarding managerial recruitment and dismissals. Support staff members reported that both frequent changes of managers detracted the ability to work professionally and longitudinally. They also suggested that the managers’ receptivity to support was reduced in periods of high pressure. Further, managers were expected by their leaders to take care of their own development. These findings suggest that managers need to be skilled in self-directed learning to avoid superficiality in work. Preparing managers for the ability to adapt effectively to contextual changes appears to not be sufficiently integrated into the current formal training of managers. Study Three employed a case study approach to critically examine how the managerial lived experience might change over time. Three managers engaged in one Norwegian PL-club (full season) and one manager from an English League One club (four months) were regularly interviewed during various phases of the managerial cycle (recruitment, employment, termination). Ethnographic principles were employed in the study that aimed to better understand how the managerial experience might change across situations and conditions. The managerial experiences changed along with sporting results (ups and downs), and differed in levels of trust and communication internally. The findings argue that shared understanding and trust across organisational levels are needed to facilitate internal stability and long-term efficiency, meaning that the skills to establish these conditions are crucial for sustained sporting and organisational success. All the managers experienced challenges at cultural, organisational and personal levels related to the different phases of the managerial cycle and technical (understanding across professions), human, and conceptual skills were needed to deal with role related challenges. Given the complexity of the role, and the continuous and rapid changes that managers are exposed to, the current study suggests that contextual insights are needed to understand and ultimately advise or prepare managers sufficiently for their future role(s). Managers need consistency in their approach to gain trust from internal stakeholders, and sporting success seems to facilitate the support. To establish managerial consistency, the manager requires a clear philosophy based on cultural, organisational and personal understandings, combined with humbleness toward knowledge.