The paper presents a constructing methodology for a modern approach to tools selection and solving the problem of assigning optimal cutting parameters for specific production conditions. The mathematical formulation determining the extreme values of the technological process optimality criteria is obtained. A system of technical and economic quality indicators for cutting tools is proposed. This system allows principles’ implementation of decentralization and interoperability “Industry 4.0” via finite element modeling of the cutting process based on solving the problem of orthogonal free cutting modeling. The proposed methodology further usage is possible by creating a standardized database on the parameters of the tool: the adhesive component of the friction cutting coefficient for processing of a specific pair of cutting and tool materials (or tool coating material) and the impacts of the cutting-edge radius on cutting efficiency of a particular material.