Observation provides applied sport psychologists with a direct assessment of client behavior within the sporting environment. Despite the unique properties and the insightful information that observation allows, it has received limited literary attention within the applied sport psychology domain. The current study aimed to explore and further understand the observation practices of current trainee practitioners. All participants were enrolled on a training program toward becoming either a chartered psychologist (BPS) or an accredited sport and exercise scientist (BASES). In total, five focus groups were conducted and analyzed using an interpretative phenomenological approach (IPA; Smith, 1996). Four superordinate themes emerged: value of observation, type of observation, challenges of observation, and suggestions for observation training. Results demonstrate the increased value that observation brings to effective service delivery and intervention. Specifically, informal observation is commended for its propensity to build greater contextual intelligence and to develop stronger client relationships.