Modern models and methods for evaluating complex systems are associated with hierarchical socio-economic systems (HSES) implemented on the basis of software systems (expert systems and decision support systems) and used at the regional and municipal levels of government. As usual, such systems have the functionality of analytics and building scenario variants for the development of research objects. However, they do not give quantified values of the state and impact factors at which the complex system under consideration can come to a given state. At the same time, the question of determining such a set state associated with the construction of standards (expected values) for elements, classes or levels of the HSES is still open. In some cases, to make an informed decision it is sufficient to obtain aggregated quantitative estimates and recommendations concerning the further functioning of the research object. This article presents the author’s approach, which allows us to evaluate the functioning of hierarchical socio-economic systems and provides expert opinions for making management decisions implemented on the basis of the EFRA software package. The algorithm includes stages of analysis and synthesis-stages of the basic method of system analysis. The novelty of the proposed approach is the possibility of taking into account the specific conditions of the status and impact of complex systems that provides an opportunity to build their own standard. Additionally, the procedures of standardization and normalization (reduction to a scale from 0 to 1) make it possible to avoid the influence of different units of measurement of results of operation and economies of scale. On the example of regions of the Central Federal district according to data for 2014–2017, estimates of the use of information and telecommunications technologies by the population were obtained, and the optimization problem was solved for the Tula Region, on the basis of which directions related to increasing the region’s readiness for digitalization were proposed.