Recently teachers have been dealing with students who belong to the so-called Generation Y, i.e., those who were born between 1980 (in Russia, it is 1984) and 2000. To have a close look at the interaction patterns with such students we applied a SWOT-analysis used primarily as a strategic planning method. A SWOT-analysis allows identifying factors of internal and external space in a company and dividing them into four categories: S (Strengths), W (Weaknesses), O (Opportunities), and T (Threats). In what follows, we will show how these categories work in relation to Generation Y. Most researchers find the strengths of Generation Y to be the ability to develop fast, to work long and hard (if such work offers financial or status rewards), and to multitask. Unlike the previous generations, modern young people have no problems in changing their residence or jobs; they find it easy to adjust to new circumstances. The majority of young people have freedom of traveling abroad (either in reality or virtually). They are communicative and idealistic as may be seen from their belief that they can easily avoid punishment or have many lives (just like new rounds in a computer game); they have access to multicultural online and offline communication, to different jobs in transnational and international companies and, finally, they are interested in the development of distance learning and the so-called freelance.