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The article outlines the main concept and examples of mathematical models needed to estimate system potential and digitalization performance indicators. Such an estimation differs in that it is performed with predictive mathematical models. The purpose of such an estimation is to enable a set of problems of system design and functional design of information technologies to be solved as mathematical problems, predictively and analytically. The hypothesis of the research is that the quality of system functioning in changing conditions can be evaluated analytically, based on predictive mathematical models. We suggested a property of the system potential (or system capability) that describes the effects of the compliance of changing system functioning with changing conditions analytically and predictively. Thus, it describes the performance of the use of information operations to realize functioning in changing conditions. The example includes system’s environment graph-theoretic models and system’s models regarding IT use to react to changing environments. As a result of the suggested models and methods, the quantitative estimation of system potential regarding information technology use becomes possible depending on the parameters and variables of the problems to be solved. Use cases of problems decision with the use of such indicators include choosing optimal information technology implementation and the synthesis of information operation characteristics.