The paper considers modern forms of flexible organization’s management systems in Russia. The aim of the research is to study the necessity and features of flexible management systems use for self-organization of employees’ work, as well as the consequences of the transition from rigid hierarchies to flexible ones. The author solved the following tasks: he described the formation of a new employee and his political behavior; analyzed the new “shop” structures that have appeared in the Russian Federation and their struggle for social rights. The study described experiments of domestic companies with “turquoise” practices and revealed specific features of self-organization in Russia. Also, the author explored flexible methods used not just in management hierarchies but also to coordinate the implementation of projects, build information structures, as well as to organize the financing of innovations in organizations. The study used the method of comparative analysis of the existing practice of applying digitalization in the economy, as well as theoretical approaches to understanding its essence. As a result, it was shown that industrial enterprises caught in the digital transformation zone had to use flexible management practices for innovative development (at least in terms of their information systems development). Nevertheless, not all of them are universal and lead to increased efficiency. The paper reveals the role of a human factor as the most important component in the innovative company management, since self-organization and implementation of changes require special personality characteristics.