This study aimed to bridge the gap in the literature on real-world analyses of coaches’ approaches to planning. A 12-week qualitative case study of a Spanish canoeing coach was carried out to examine the relationship between long- and short-term planning, analyze adaptations made to the original designs, and thus, enhance current understanding of this dialogue in a specific real-life context. To achieve this purpose, the first author followed the participant during training sessions in an unobtrusive manner, recording any relevant topic related to the research goal in the form of field observation notes. Weekly semistructured interviews were also carried out. Data were examined through thematic analysis, and two main themes were identified: (a) interplay and tension management between short- and long-term planning and (b) the dynamic tension between club and national team planning. Findings observed that the coach’s application of concepts related to planning usually had to be adapted. Indeed, external factors and demands obligated the coach to attribute more emphasis to short-term planning, despite the existence of a long-term plan. Moreover, findings established the need to understand sports planning as a micropolitical process, influenced by external pressures, organizational demands, and the constraints generated by sports practitioners.