Extensive research highlights the important roles of coaches and parents in fostering positive youth development (PYD). However, little research has examined the complex coach–parent relationship in the bidirectional interactions of the coach-parent-athlete triad. This research is particularly pertinent in elite youth sport, wherein the performance-oriented environment may impede the pursuit of PYD. As such, this study aimed to deepen understandings of the coach–parent relationship in relation to athletes’ PYD. Specifically, the first author critically analyzed and reflected on his experiences as an elite youth ice hockey coach, thus offering a unique portrayal of reflective practice in the context of sport coaching. Two interconnected themes emerged: understanding conflict in the coach-parent-athlete relationship and fostering collaboration through enhanced coach–parent communication. Findings and reflections are discussed in relation to the dual-concern model of conflict resolution, and strategies to help practitioners foster cooperative coach–parent relationships are presented.