The complete self-management organization, where there is no existence of organizational hierarchy, is only found as isolated cases in certain Western organizations, and there has been little scholarly discussion or research on this topic. However, in recent years, there has been a daring experiment in a specific company in South Korea to introduce holacracy, a form of self-management organization. Although it ultimately failed to establish itself, it is considered the first case of introducing a self-management organization in organizations of a certain scale. In this study, an in-depth case study was conducted on the entire process of introducing, implementing, and failing in the adoption of holacracy in this company. Despite the strong determination of management, the study aimed to explore the reasons for the failure in introducing a self-management organization and identify the necessary requirements for successfully implementing it. The key findings of the study are as follows. Firstly, there is a need for preparedness in terms of capabilities and attitudes among members. Introducing a self-management organization means a complete departure from traditional ways of performing tasks. Therefore, strong intrinsic motivation for autonomy, where individuals can perform their duties autonomously without relying on superiors' instructions or control, is necessary. This requires essential job expertise that enables individuals to autonomously fulfill their responsibilities. For those who have previously held managerial roles in conventional organizations, a job- and role-centric attitude that allows them to perform their duties autonomously, without relying on giving instructions or control to the members, is required. Secondly, the organizational design and operational capabilities of the CEO and the organizational change team are crucial. Holacracy, being a departure from traditional hierarchical organizational structures, requires the CEO to design the organizational structure in alignment with enhanced autonomy and accountability, decentralized decision-making, and task flexibility. The CEO should clearly define and distribute roles and responsibilities within the organization, fostering a culture of continuous learning and development for both themselves and the organizational members. Particularly, anticipating and planning for crisis management strategies in advance is necessary. Therefore, the higher the CEO's and the organizational change team's capabilities in holacracy organizational design, the more effectively the organization can respond to changes and grow innovatively. Lastly, for successful implementation of holacracy, a long-term perspective and gradual adoption are important rather than a radical approach. In this study, four procedural steps for the gradual introduction of holacracy are proposed, aiming to sufficiently explain and share the organization's direction and decision-making rationale with its members to build trust. It is also necessary to consider options for providing exit routes, such as resignation or job transition, for members who are unable to embrace organizational change. Through these measures, after the introduction of holacracy, members can enhance their understanding and adaptability to the new organization, minimizing resistance to abrupt organizational changes and enabling the successful establishment of a self-management organization.