Although human flexible behavior relies on cognitive control, it would be implausible to assume that there is only one, general mode of cognitive control strategy adopted by all individuals. For instance, different reliance on proactive versus reactive control strategies could explain inter-individual variability. In particular, specific life experiences, like a highly demanding training for future Air Traffic Controllers (ATCs), could modulate cognitive control functions. A group of ATC trainees and a matched group of university students were tested longitudinally on task-switching and Stroop paradigms that allowed us to measure indices of cognitive control. The results showed that the ATCs, with respect to the control group, had substantially smaller mixing costs during long cue-target intervals (CTI) and a reduced Stroop interference effect. However, this advantage was present also prior to the training phase. Being more capable in managing multiple task sets and less distracted by interfering events suggests a more efficient selection and maintenance of task relevant information as an inherent characteristic of the ATC group, associated with proactive control. Critically, the training that the ATCs underwent improved their accuracy in general and reduced response time switching costs during short CTIs only. These results indicate a training-induced change in reactive control, which is described as a transient process in charge of stimulus-driven task detection and resolution. This experience-based enhancement of reactive control strategy denotes how cognitive control and executive functions in general can be shaped by real-life training and underlines the importance of experience in explaining inter-individual variability in cognitive functioning.