As a result of research, the concept of a flexible evolutionary model is proposed, which with the help of machine learning allows obtaining the most successful strategy for the development of human capital. The proposed conceptual and methodological approach to machine learning of the process of assessing human capital of enterprises, taking into account the cognitive psychology of man and reflective attitudes in the human environment, can increase the effectiveness of decision-making in the field of human capital development management. The training involves indicators of return on investment in the individual, in the types of components of human capital, which are characterized by properties (creativity, competence, purposefulness, communication, motivation), where between their varieties there are appropriate reflective relationships. The main difficulty of this approach to the choice of alternative solutions for finding options for the use of human capital is the correct selection of indicators of significance (return) of contributions to the development of types of human capital, on the basis of which cycles occur of systemic learning. This approach can simplify the search for and developments of human capital development strategies, present alternative ways, and simplify management decisions.