This study explored parental concerns regarding their sons’ experiences in a professional football academy, using a case study methodology over a twelve-year period. Drawing on over 60 interviews with parenting pairs, the research identified that concerns were shaped by internal (e.g., personal beliefs), semi-internal (e.g., peer influence, agent input), and external (e.g., social media, educational trends) information sources. These sources often led to misaligned expectations between parents and the academy. The findings highlighted the prevalence of misinformation. In response, a series of targeted interventions were implemented, including structured communication strategies, shared mental models (SMMs), and a refined parent–academy code of conduct. These changes facilitated more integrated parent–athlete–coach relationships and improved clarity around developmental processes. Although causality cannot be established, the frequency of parental complaints decreased over time. This study emphasizes the need for academies to proactively engage parents as key stakeholders through clear, consistent, and evidence-informed communication, ultimately supporting a more coherent developmental experience for athletes. These findings have broad implications for talent development environments aiming to balance athlete and parent welfare with high-performance goals.