The environment of entrepreneurial activity is numerous and heterogeneous. It includes a large number of components that influence the organization in a different extent, nature, and frequency. The question of assessment methodology of the entrepreneurial activity strategic risk factors is sufficiently important. The aim of this paper was to develop an assessment methodology model of the strategic risk factors of entrepreneurial activity with the application of a scenario-based approach to identify dependencies of the risk factors using statistical data for 10 years. Changes in the external common business environment mean strategic risk factors. The following methods were used in this study: a) questionnaire of entrepreneurs and managers of small and medium enterprises, the Central Bank staff, and scientists for the purpose of selection of indicators characterizing the external business environment; b) correlation analysis; c) regression analysis; d) Delphi approach; and e) scenario analysis methods. As a result of the conducted study, the main factors exerting the most significant influence on the entrepreneurial activity were identified Furthermore, a working hypothesis concerning the fact that an increase of standalone strategic risk factors does not always exert negative influence on the entrepreneurial activity was confirmed. The proposed tools of risk factors assessment and their influence on the entrepreneurial activity may be used for the assessment of both the organization environment and various risk situations aimed at further use of the obtained information in decision-making.