The article pays attention to the problem of misunderstanding between teachers and students that causes the lack of motivation to the process of learning on the part of both teachers and students. Generation gap and difference of ideas and values are considered as the main reasons for the situation. The theoretical basis of the article is the Theory of Generations by William Strauss and Neil Howe and its interpretation for the Russian environment by Eugenia Shamis. Several generations of teachers and students are characterized according to historical, social, political and economic circumstances that influenced their personalities and worldview. The article also points out strategies used by people of different age group for finding and processing information. The author provides tips for successful collaboration of different generations. The Internet is stated to be the main area that is able to unite and to conciliate modern teachers and students. Every teacher is to catch up with the changing technologies and master new Internet resources in order to be up to date and on the edge of news, innovation and expertise. The generation of Web 1.0 recourses is becoming obsolete and the new type of platforms belonging to Web 2.0 is taking their place. Teachers are advised about how not to lose their way in the great amount of online resources available and to manage time properly in order to have an opportunity to make lessons informative, interesting and useful for the coming generation of students. Students are suggested a few tips to help them find their way in the world of information, organize, store and use the existing knowledge assets properly in order to enjoy the process of learning and to avoid possible conflicts and misunderstanding.