The aim of the paper is to increase understanding of the succession decision-making process in family businesses. In understanding this phenomenon on the personal level of reality and understanding the decision-making process involved in succession, the decision-maker’s thought process and aspirations have to be taken into consideration. Based on a survey, a knowledge-based expert system tool (Doctus) was used to order successors’ intuitive knowledge and aspirations in order to deepen our understanding of the succession decision-making phenomenon. The diversity of the identified rules suggests that first generational change does not happen according to a single model but rather a variety of pathways are followed, depending on the context.