The practice of strategy decision making proves that when the management board is strongly limited in its capacity to take rational actions, specifically in the context of great decision complexity and uncertainty, it is considered good practice to refer to experience through reasoning by analogy. In this paper, we would like to concentrate on supporting strategic decisions in small and medium enterprises (SMEs). The complexity of analogy-based reasoning has its roots in an attempt to solve new problems based on past cases from a different domain, while we will focus on case-based approach for a single domain. Additionally, we have chosen case-based reasoning as a suitable decision-making paradigm because it is corresponds to managers’ decision-making behaviour. We present the STRATEGOS case-based reasoning system for supporting strategic decision making by SMEs management boards and then the system evaluation by the dozens of chief executive officers (CEOs) from SMEs is presented. The results of the survey are promising and show the remarkable correspondence of the proposed solution with expectations and strategic behaviour of CEOs.