By examining a large number of literature sources, it can be ascertained that the characteristics, preferences and interests of individual generations are different. The focus in this final paper is on two generations - Generation X and Generation Y, particularly on their expectations and motivation related to their working careers and the existence and amount of communication misunderstandings and generational differences. The conducted empirical research includes 194 employees who are of these two generations. The main aim of the research was to identify potential misunderstandings between the two generations, and to gain a deeper insight into their perceptions of work and career. The results of the research are partially confirmed by previous research. There is no significant incidence of communication misunderstandings between generations, although, there are differences in preferred forms of communication. Regarding perceptions of working values, work environments, business activities and interactions, significant differences have been obtained on a small number of aspects, and they relate to teamwork preferences, leadership perceptions, structured workplace, spirituality and integrity.