Each new generation brings a challenge to employers, university management and teachers with new attitudes affecting their continuous matriculation and degree completion. This article discusses how to retain both business and institutional career-oriented students using real-time communication based on their attitudes, emotions resulting from logically generated synonyms by automatic data evaluation by the information system. The objective of this article is to identify these students early in their academic studies and to assess their likelihood for continuous matriculation and ultimately increase retention rates. Using data from entry questionnaire during application at university, based on their attitudinal expectation, students were categorised into groups that affected their continuous matriculation. Data used in this study were gathered by compulsory entry questionnaire of 535 students in the academic year 2017-2018. Using statistical and dimensional analysis, four groups were identified among university applicants: Proactive, Reactive, Lazy and Institutional. Responses were tested according to Complementary Distribution Function (CDF) and normal distribution as Probabilistic Distribution Function (PDF). Antagonist attitudes were found for answers corresponding to PDF and CDF. Results indicate that business and institutionally oriented students should be separated and treated individually to increase retention.