New technologies and digital solutions are currently rapidly entering the construction machinery sector. These include (partial) automation solutions for machines and the implementation of the first autonomous construction machines, which no longer require machine operators. The first of these can help relieve the personnel shortage in the future, but qualified skilled workers will still be needed to operate the construction machines. The qualification requirements will increase massively due to the increasing complexity of machine technology and the use of new technologies. Efficient and, above all, safe handling of the new machines and construction processes will be achieved not only by integrating new technologies, functions and machine types into the training and qualification content, but also by adapting the content of these training and qualification programs to ensure a high level of acceptance among operators. This publication deals with the changes that operators are facing as a result of the digitalization of their occupation and analyzes the resulting challenges for the training and further education of machine operators on the basis of an exemplary activity.