The overall aim of this paper is to share our experiences in development, implementation, and evaluation of an intervention designed for establishing interorganizational collaboration in talent development between a Danish sports club, a municipality, and a federation. Yet, despite a neat plan, we faced several challenges in what turned out to be a less successful intervention. The account is based on the first author’s field notes, informal interviews, and intervention debriefings. The professional philosophy of the research team was informed by the holistic ecological approach and an empowerment approach. We used the pyramid model for optimizing interorganizational collaboration in talent development as a framework to design and guide the 7-month intervention that included four workshops covering (a) initiation: building relationships; (b) exploration: foundation for the shared philosophy; (c) clarification: negotiating values and strategy; and (d) implementation: from talk to action. However, challenges (e.g., resignations of key stakeholders) led to program adjustments and, ultimately, termination. This paper shows the nuances of a less successful intervention, which can help practitioners plan and carry out better interventions in the future. Despite the challenges faced here, we still deem the pyramid model for optimizing interorganizational collaboration in talent development a valuable framework for practitioners working at an interorganizational level.