Information security and data protection are currently important elements of the activity of any enterprise. The changes taking place in the global economy stimulate the emergence of new software products that reduce the risk of confidential data leakage. The article proposes a solution to the problem of monitoring and evaluating the communications of enterprise employees with customers, customers and partners. As a result of the study, a software system for monitoring and evaluating two types of messages was developed: voice and text. The main method in the development of this monitoring system is a technical and forensic analysis. With its help, a software implementation of the system was created in the C# programming language. The program consists of two main functional parts: the first part is designed to process audio files, the second is responsible for the analysis of text messages. Also, a detailed description of the main procedures of the program operation is given, taking into account differences in the methods of storing and processing data, which is justified by different formats of the analysed files. Using the developed program can help the enterprise build a communication strategy to reduce further possible costs and identify as much data as possible about intruders. In the future, this system can be improved, and supplemented with functionality and a more user-friendly interface.