Purpose. The purpose of the study – taking into account the functional load of the system of controlling, monitoring and diagnostics, to determine a methodical approach to performance control in the process of monitoring production parameters of agricultural enterprises’ functioning and diagnosing problematic aspects of financial and economic results to justify management decisions when planning promising production programs. Methodology / approach. Studies were conducted on the basis of general scientific methods (in the study of the theoretical basis of the functions of controlling, monitoring, and diagnostics of management activities in ensuring the effectiveness of management decisions in planning the sown areas structure), abstract-logical (to generalize the influence features of intensive crops use degree on the effectiveness of the grain direction of agricultural enterprises), economic and mathematical (to identify the optimal strategy in terms of information uncertainty in the agricultural enterprise management associated with the presence of faintly structured problems), statistical methods (statistical solutions theories for modeling the mechanism of crops interaction in given conditions of natural resources), and constructive (determining the method of substantiation of optimal resources flows and results of activities in order to maximize the profitability in the condition of the constancy of the resource base). The methodological basis in processing material is the dialectical method of social and economic phenomena perception. Results. In the course of the research, the conditions of formation of effective system of agriculture entities and diagnostics prerequisites of possible management actions to ensure sustainable profitability were analyzed. It is established that a critical increase in the sunflower share in crops is a reactive behavior of management practice in the conditions of the Luhansk region. The dependence of management decisions on planning the structure of sown areas by the perception of favorable economic conditions is proved according to the diagnostic analysis. The main parameters of statistical modeling for the implementation of diagnostic functions for identifying probable management actions in ensuring sustainable profitability of enterprises are determined. Originality / scientific novelty. The scientific novelty of the presented research is to improve the methodological approach to the implementation of controlling, monitoring and diagnostic functions in the process of substantiation of a promising production program of an agricultural enterprise in these conditions, which, unlike existing ones, is based on the methodology of statistical decision theory, high financial and economic efficiency in the study of information (parameters) about the technological discipline, which has no clear mathematical (regression) relationship. Practical value / implications. As a promising task for the development of the system of controlling, monitoring and diagnostics, it is determined the formation of mechanisms for programming the development of grain farming as the main specialization direction in the steppe conditions of Luhansk region on the principles of sectoral competitiveness, which will partially eliminate the reactivity of the management system of agricultural enterprises.