The digital transformation has affected all economically developed countries in the world including Russia. The issues of transition to the digital economy are considered at the highest level: the decrees of the President of the Russian Federation created national and federal projects, including in the higher education system. But the transition to the digital environment is rather slow. The article presents an assessment of the current state and trends in the development of the domestic system of higher education, identifies the problems of transition of Russian universities to the digital educational environment. The purpose of the article is to generalize and systematize the existing developments and create a methodology for assessing the degree of universities willingness for digitalization. The authors have systematized and expanded the list of factors for assessing the willingness of universities for digital transformation. The main research methods are: expert assessment method, morphological analysis, cluster analysis. The matrix of factors and their features formed the basis for ranking indicators and forming clusters. The method proposed by the authors is universal, it has been tested at one of the Russian universities – NSTU NETI and can be applied by any institution of higher education to assess the willingness of the University for digitalization.