The staff shortage is an issue that is becoming increasingly prevalent on a global scale. One of the increasingly relevant approaches to overcome this problem is the digital transformation of business. The strategic choice of a company in conditions of labor shortage comes down to a managerial trilemma: increase labor costs or invest in technologies that can replace missing employees, or implement a combination of investments in labor and technology. Each of these strategies has its advantages, costs, and risks, and requires economic justification as a long-term investment decision. The article presents a study of the possibilities of substantiating the company's decisions on investments in human capital and digital technologies in conditions of personnel shortage based on the application of models and methods of managerial economics. The author of the article has studied the current and predicted manifestations, scope and consequences of the shortage of human resources, as well as the existing approaches of companies to this problem. It is concluded that in the process of making a firm decision to replace scarce human resources with digital technologies, the following factors should be considered simultaneously: the ability to achieve long-term competitive advantages with additional labor and/or capital costs; the ratio of productivity to the price of these resources; the comparative magnitude of the risks of investing in each of them and the possible damage from unsuccessful investments; and the optimal scope and timing of the implementation of innovation for the current and desired competitive position. The article may be useful for researchers in the field of human resource management, digitalization of economy and business, academic staff, students and postgraduates of economics, and practitioners.