Surveys show that only every third company in Russia has chosen a digital transformation strategy and has implemented it. What slows down the development of these kinds of strategies in companies? The choice of the strategy is partly defined by the level of readiness of the company’s management system, business processes, architecture, etc. Existing tools of evaluating companies’ readiness for digital transformation lack of universality, formalization and often use highly professional terminology. The study is aimed at answering the questions of whether the key terms concerned with digitalization are understandable by Russian companies and whether it is possible to use existing criteria systems to assess companies’ readiness for digital transformation. The article presents the results of a survey of Russian companies’ representatives conducted using a questionnaire developed on the basis of the proposed approach for evaluating readiness. The approach involves the sequential decomposition of the objects of estimation and the grouping of their characteristics and sub-characteristics into the following domains: system management, maturity of the company’s architecture, readiness of business processes, maturity of data management, and personnel readiness.