Based on a number of approaches to the life cycle formation, which help to consider and formulate the specific character of crises of development and the recommendations on development from various viewpoints, a model of analysis of the life cycle of a company and factors ensuring its development in the long term has been identified by the Dutch authors B. Lievegoed and F. Glasl. The conclusion is made that the model of a life cycle presented by these authors differs from other well-known models. The most significant difference is the interpretation of the development stages of the company, in which the center of scientific view on the organization development cycle phases is its managerial capabilities. The role of the “relation space” is considered, which in addition to the “activity space” forms managerial capabilities to overcome development crises. The practical part summarizes the results of an analysis of four medium-sized enterprises in the transition from a differentiation phase to an integration phase, which demonstrate the focus of attention of the employees interested in the development of their company. The leading role of the analysis of the “relation space” is shown in diagnostics of the problems of development by employees and in the formation of managerial capabilities in the process of analytical activity. The relevance of the used model presented by B. Lievegoed and F. Glasl for the analysis and design of development of a medium-sized enterprise, which is in the stage of a transition to the integration phase, has been demonstrated. The conclusion is made on the difference in the formation of managerial capabilities for small, medium-sized and large enterprises.