Ethical behaviour and honesty had an ambivalent meaning in the Soviet Union compared to the Western approaches. The aim of our research is to analyse generational differences with regard to honest behaviour and honesty as a personal value in Post-Soviet Business Environment: in Estonia and Latvia. In this study we explore differences in approaches towards values and especially honesty amongst four generations of retail sector employees-starting from those, who were still to great extent exposed to pre-Soviet values, continuing employees who started their careers during the Soviet times and ending with those, who were educated and entered the workforce after the collapse of the Soviet Union. 781 service employee from 6 retail organizations in Estonia and Latvia were surveyed to assess likelihood of dishonest behaviour and to rank their values according to the Rokeach instrumental value scale. Arguing that for post-Soviet countries rather specific events and timelines could have left the main impact on worldviews, in order to assess the generational differences, we define four generations currently active in the workforce - Post-war generation, Early Gen X, Transition generation and Millennials. We confirm that despite dual morality and ambiguous ethics in the Soviet Union, twenty-five years after the collapse of the system retail sector employees tend to report likelihood of rather honest behaviour. Moreover older generations report higher likelihood of honest behaviour than younger generations. And Post-war and Early generation X, born between 1945 and 1970, rate honesty and responsibility higher as their individual values. We also find that in a post-Soviet context there are significant differences between early and late generation X, at least as far as honesty in the retail business environment is concerned. Originality of this study is the following - the complexity of generational differences towards ethical behaviour, values and honesty amongst them has not been widely researched in Post-Soviet business environment.