This work highlights problems of using digital technologies to manage small and medium businesses. The purpose of this study is to identify problems and difficulties, as well as approaches to solving these difficulties for real businesses when solving the problem of configuring a company management system. The authors conducted a comparative analysis of popular business management systems, which allows us to verify the existing complexities of configuring and designing the management environment. The results of the review of international articles on business management, the analysis of modern business management information systems allow us to see the presence of problems of automation and implementation of information systems in small and medium businesses despite the rapid growth of technologies. The authors draw attention to difficulties in implementing digital technologies in the management of small and medium businesses and offer a number of solutions that will allow owners of micro, small and medium-sized businesses to mitigate the difficulties and use the potential of digital technologies to configure the management system of their company.