The aim of this article is to understand how advisory services addressing farm management issues can foster strategic thinking. We consider that the evolution of strategic thinking is related to the concept of proactivity. In Benin, we analyzed the impact of learning processes triggered by an approach called “management advice for family farms” (MAFF) with a sample of 19 farmers. By providing technical and management training, the MAFF approach enables farmers to better understand their environment, assess their situation, and act differently. The participants' strategic thinking evolved after one year of participation in MAFF activities. This evolution is partially dependent on the level of resources or level of education of the participants. However, the level of proactivity before the training is a strong element influencing the intensity of the learning process.