This article considers the psychological issues related to generational differences in the context of university culture. The data were collected electronically from two key internal stakeholders of one of the entrepreneurial Russian universities, namely, 118 employees and 117 students, experienced university onboarding in the first academic year. The results show that gen Z differs significantly from the other generations regarding the levels of neutral identification and disidentification. It may be concluded that the students undergo in some way complexity in the adjustment to the university environment. All generations demonstrate the significant discrepancy between the current and preferred organizational culture. The most considerable gap was established for market culture type. Each generational group did not accept market values and preferred working in a clan supportive environment. This article contributes to understanding the peculiarities of management in modern university settings, studying university culture, psychological features of the representatives of different generations and key internal stakeholders.