Modern requirements to competitiveness, especially in the leading industries, set the priority of the development of enterprises in the energy sector. Projecting the organizational development of power supplying companies are considered as a complex problem, which has the various technical and organizational components, the implementation of which involves non-trivial approaches and increased costs. Therefore, to manage these projects is advisable to use a proactive approach and develop the specially adapted models and methods within the proactive management. In order to ensure decision-making on the managing the power supplying company transformation project, it is necessary to develop the predictability of the parameters of the project implementation processes. The estimation of the status of the project implementation is carried out according to the value of the indicator: the amount of project work. In the experimental study, the productivity and effectiveness of the proactive managing the power supplying company transformation project in Ukraine are considered to check the the proposed method adequacy. Consequently, the experimental study proves that to solve the proactive managing problem of the organizational development project based on the proposed method is not to identify the detected deviations but to determine their magnitude and acceptability in terms of achieving the goal of the project, allows a minimum upper limit for relative deviations from all the maximum values of the target functions obtained as a result of the solution, that is more effective than the known methods. Thus, the proposed method improves development of observation of deviations in the field of “chaotic proximity”, their identification regarding the actual state of the system, and manageability of the project implementation by developing appropriate actions: stabilization, balancing or maneuvering for achieving the goal.