Management and control depends on information in all areas. Therefore, the increasing capabilities of the information technology increase management potential. Trying to rely on the knowledge of all employees of the organization, top managers often care about collecting, exchanging and digitizing a large amount of data. However, this does not guarantee increased competitiveness of the organization. In the section "Heroical Sisyphus IT-tasks" by an example of comparing the results of a study of the difficulties and causes of professional burnout of IT specialists in Russia and the USA is shown that one of the main factors of their stress is the specific features of top-management work, in particular, their expectations and setting goals for implementation of the knowledge-management, not leading to the developing of a self-learning organization. Another factor of stress and failures in the knowledge management is associated with an increasing number of constantly updated types of information technologies, which is discussed in the section devoted to typical errors in supporting knowledge management projects, forecasts for the development of the IT-branch and problems of misunderstanding in communication of IT-specialists and other specialists in a company. The last section is devoted to the risks of treating knowledge as capital and the contradictions in the formulation of knowledge management tasks by HRmanagement of companies on one hand and specialists who have the opportunity to work as freelance in the modern labor market conditions on another hand. Thus, it turns out that in the knowledge management not the amount of collected data, but its integration; does matter, not the large databases and not even the speed of their use, but the cooperative development of decisions based on the knowledge of the current situation, distributed among the company's employees. This managerial task can not be solved by digitalization methods. Although a reasonable reliance on the growing possibilities of digital technology may be very useful.