The purpose of the present study is to investigate how learning experiences acquired through workplace coaching may affect stress. I identify two main learning experiences in the coaching process, insight and planning skills, and propose that these affect stress directly and also indirectly through mediators’ job demand, job control, and social support. A within-subject, longitudinal design is applied, with 56 persons receiving coaching from professional, external coaches. Data was collected at three points in time: baseline (before coaching), after a three-month period of coaching, and a follow-up nine months later. The results show that planning skills acquired through coaching reduce stress in the short term, and that the effect is mediated through a decrease in job demand. The decrease in job demand is further shown to reduce stress in the long term. Insight as a coaching outcome is not directly related to stress; however, insight affects social support, which in turn is associated with reduced stress in the long term.