In the paper an approach has been proposed that can support city management in line with Smart City 3.0 in the context of attracting and retaining human resources capable of identifying and undertaking ICT initiatives. Smart City 3.0, unlike previous versions of this concept, put a lot of emphasis on human and social capital. Here, the creative involvement of residents is to dominate. These are to be smart civic cities, open to the active participation of residents and encouraging such attitudes. The administration should create conditions and opportunities to harness people’s potential. The technology is rather a tool. And people need power to act. This strategic, long-term vision focuses on attracting and retaining human resources, critical in building the Smart City concept. In this context, the question is asked: How to acquire Smart People to build Smart Cities? An approach has been proposed that allows to discover knowledge about what combination of people’s characteristics and the image of the city makes people want to link their careers with the city or want to leave it. This knowledge may be important for decision-makers and indicate what image the city should build to attract the desired people. The research focused on well-educated young people who were making decisions about their career path after graduation. The flexibility and applicability of the proposed approach allows it to be used also for other target groups. The survey was conducted among management students from the University of Szczecin and Częstochowa University of Technology. A total of 286 students participated in the study. The discovery of knowledge hidden in data was carried out in accordance with the Rough Set Theory. The Rough Set Theory enables the induction of decision rules that take a form that is easy to understand and interpret: if premise, then conclusion. Additionally, the rules have qualitative characteristics. Example rules and their interpretations are presented in the article. In this part of the research arguments and evidence have been provided for the usefulness of the rough set theory in this field.