This article provides an in-depth exploration of the nature of the cultural shift in business norms in two former Soviet Union republics: Estonia and Belarus. While questioning the linearity of existing models describing social—cultural change and, drawing on Lotman’s model (1990), the paper points to a complex interplay of past and present, Western and local traditions in the transformational context of the post-Soviet countries. The analysis is based on a set of semi-structured in-depth interviews with Belarusian and Estonian entrepreneurs, who conveyed their attitudes towards transition and current management practices in the region. Exploring the issue on both a temporal (pre-Soviet and post-Soviet) and a spatial (Western/non-Western) axis the paper discusses the relationship between the ‘importing’ and ‘exporting’ of values, which take place across each of them, and concludes with what the analysis can tell us about cultural transformation more generally.