Observation of performance forms a critical part of the complex coaching process. A professional judgment and decision making (PJDM) framework enables optimum decisions to be made under time pressure and with limited information that derive from that observation. Observation and the associated decision making can be particularly affected by heuristic bias. We extend the work on PJDM via a greater focus on its relationship with observation within the coaching process. After revisiting PJDM and observation, we introduce and explore heuristics as a “tool” within the observation process. Specifically, we propose that observation is prone to heuristics built on a coach’s experience and understanding. We report on a small scale preliminary investigation with a group of high-level paddle sport coaches. We identify heuristics that both restrict and enhance the effectiveness of the observation in an effort to promote discussion and further research.