The paper´s objective is to define significant technological factors in the areas of human capital availability and research and development affecting the quality of small and medium-sized enterprises (SMEs) and their business environment, and to quantify differences between the Czech Republic (CR) and the Slovak Republic (SR). Based on the objective, empirical research was conducted including data from 312 SMEs in the CR and 329 SMEs in the SR processed with the use of Chi-squared tests and Z-scores. The research showed differences in assessing defined technological factors between the CR and the SR, and also confirmed a low level of the assessed factors in both countries. Furthermore, overall satisfaction with the quality of secondary schools and universities is relatively low despite the fact that the research showed a higher level of satisfaction with the quality of university education in both countries. In the Czech Republic, entrepreneurs largely experience a shortage of skilled workforce, with this factor achieving the highest negative rating. The Slovak entrepreneurs most negatively assessed the level of state support of research and development. Moreover, the entrepreneurs´ overall level of satisfaction with the research and development infrastructure is relatively low, since only 23.08% of the Czech and 13.68% of the Slovak entrepreneurs agreed that the infrastructure is well built in their respective country. Similar results were also obtained in assessing state support of research and development. At the same time, it was found that research and development results help the entrepreneurs only to a limited extent, and the entrepreneurs in both countries are not very optimistic about future development of their business activities.