The article is devoted to solving the problems of assessing the quality of software documentation in the training of software developers. Various CASE-tools are widely used at present to improve the efficiency of the software development process, including the preparation of documentation. However, it is necessary to improve methods and means of automating the formation of software development skills that contribute to improving quality and accelerating the learning process. The methodology for assessing the quality of the generated software documentation (on the example of the software testing process) in the course of students performing practical tasks is considered. The methodology is based on the use of mathematical methods, in particular, expert assessment methods. The article also describes a prototype of a subsystem (which is part of an automated training system) used to assess the quality of practical tasks. The advantage of applying this methodology when training at an enterprise is the ability to increase the level of professional skills, speed up the process of adaptation of young employees, and also (when evaluating experienced employees to perform real tasks) improve the quality of the documentation itself.