The involvement of people and technical devices is a characteristic feature of technological processes in agriculture. Human access to modernized and more efficient technical equipment determines the differentiation of the proportions of the contributions of human labor and technical equipment to the implementation of production technology on farms. Taking into account the data on manual and machine work inputs, the methodology of determining the technological index level (TL) was presented. The aim of the present study was to present the scope of use of the technological index level to assess the effects of technological progress in the dairy production system, with particular emphasis on cow milking. For the value range of the technological index level (0–100%), changes in the milkman’s work efficiency were presented based on research carried out on farms equipped with milking equipment at different levels of technical advancement. Moreover, the course of changes in electricity and water consumption per liter of milk was determined in association with the technological index level. The issue of simultaneous implementation of various forms of progress was developed based on the example of milking cows with a milking robot. Five categories (ranges) of cows’ milk yield were distinguished and compared with the current yields of cows in the European Union. On this basis, a discussion was initiated on the factors that facilitate and limit the implementation of technical and technological progress in dairy production.