Career guidance and counseling have been gaining importance in the last ten years. Given the changes in the labor market and the context of the Fourth Industrial Revolution, the young person must be prepared for these changes. The research aimed, as a part of the broader and long-term scientific scope, to evaluate the situation of career counseling and learning from the perspective of secondary school students in the Czech upper secondary vocational schools (ISCED3). Specifically, the question was asked about what these pupils expect in terms of career learning and how schools, in reality, respond to this demand. A questionnaire survey (N = 1126) provided feedback on 21 topics relevant to vocational training and career management. Factor analysis identified four basic types of pupils in terms of their needs: Pragmatic, Personality-oriented, Seekers and Ambitious. The examples of strategies and methods suitable for working with identified categories of pupils are discussed.