This paper analyses the strategic behaviour of small and medium-sized enterprises (SMEs) and identifies the entrepreneurial, technological, and administrative problems of the Miles and Snow typology (1978). This typology is applied to a sample of SMEs in the Canary Islands (Spain) by using a multi-item questionnaire. Then, the Rasch Measurement Theory is applied to obtain the results, with the linear continuum as a key tool. By applying the Rasch Measurement, there is a coherency between the data treatment and the new interpretation of the Miles and Snow typology (1978), which lists 4 types that are close to trends than to pure types (for example, Sollosy 2013). There are differences between the administrative and the technological problems, with their technological approach being more prospector and their administrative one, which is more defender. This shows an almost absence of enterprises with purely defender or prospector behaviours. These results show that SMEs do not follow any comprehensive framework in order to develop their strategies. Managers should analyse their strategic situation and consider the alignment of the three problems.