This study delves into the nuanced interplay between the ownership competencies of family business owners and the multifaceted dynamics surrounding the sale of their business. It challenges the existing literature by focusing on the less-explored post-sale phase, a period critical for former owners, their families, and stakeholders. The research utilizes a multiple-case study design, examining seven multi-generational business families in Italy and Denmark, to understand how family businesses navigate the complexities of sale events. The study builds upon the ownership competence theory, examining how these competencies—matching, governance, and timing—are applied during and after the sale of a family business. It investigates the evolution of family business owners' roles, from operational to strategic, through the lenses of psychological disengagement and strategic decision-making during critical transitions. The findings reveal a nuanced characterization of ownership competencies in family businesses and demonstrate how these competencies are strategically employed during significant events like the sale of the business. This research contributes to the understanding of family business dynamics, particularly in managing transition events, and offers insights into the strategic application of ownership competencies in navigating these complex scenarios.