Personalities and work values of individuals are among the important factors affecting business life. Understanding the differences between generations in work environments is the first step in caring for the values and needs of employees. Since each generation has different characteristics, organizations also have to update their systems according to the expectations and needs of the generations. In this context, the aim of the research is to analyse the relationship between five factor personality traits and work values within the scope of generations; to put forward determining evaluations about the personality traits and work values of the generations in Turkey. In order to obtain the findings of the research, the survey method was applied, Super's Work Values Inventory and Goldberg's Five Factor Personality Inventory were used. The sample of the study consists of 411 people from different occupational groups, Silent Generation, Baby Boomer Generation, Generation X and Y, living in different regions of Turkey. The differences in work values and personality traits between generations were measured by Anova and Post-Hoc tests, and the relationship between work values and personality traits within the scope of generations was measured by correlation analysis. According to the results of the study, it was found that the work values and personality traits of the generations are generally supported by the studies in the literature, and there is a positive but low-level significant relationship between the five factor personality traits and most of the work values within the generations.