The research aim was to identify the training needs of entrepreneurs and employees within small and medium enterprises (SMEs) from the Suceava, Chernivtsi, and Bălți regions, to analyze the specific training practices in the cross-border area, and to identify the common features or the disparities. The research contains an exploratory survey, based on a semi-structured questionnaire that investigates the training needs in the SMEs and specific training practices with a comparative approach. The results relate to the challenges faced by transformation economies and by the specificities of SMEs from these remote areas. Additionally, the research connects the factors involved in planning and delivering training programs for employees in SMEs in this EU peripheral area with the weaknesses of the companies in facing the market competitive economy. The results of the survey disclosed some common features and specificities related to training needs, training responsibilities, and interests in the SMEs from this cross-border area. The discussions are relevant for different categories of stakeholders, at the micro-level, for the management of the companies, but also on a larger scale, in planning the new development programs for the labor market in the targeted areas.