Current theoretical frameworks for assessing policy implementation have been developed almost exclusively in the context of market-based, pluralist democracies. The lack of applicable implementation theory outside this ‘western’ setting inspired this research to investigate policy processes in more diverse contexts. This research thus applied existing implementation theory to the post-Soviet sphere, utilising current frameworks to test conditions in a post-communist context. This policy lens approach was applied through two in-depth case study policies within the small and medium enterprise (SME) sector, in order to improve practical understanding of the ongoing transitional complexities in the region. The choice of SMEs as policy targets shed particular light on the development of the middle class, which in turn contributed insights regarding post-Soviet nations’ continued transition towards more liberal democracies. This research examined implementation effectiveness through fieldwork conducted in Ukraine (2012), using an amalgamated list of criteria for ‘perfect’ policy implementation as a theoretical framework (Allison & Halperin, 1972; Gunn, 1978; Mazmanian & Sabatier, 1983). Empirical data was collected through both qualitative and quantitative methods, including interviews (141), surveys (178) and primary source collection. Data was analysed through a combined approach of interview coding, process-tracing and cross-tabulation. Findings confirmed that incorporating certain socio-economic features, specific to a post-Soviet environment, into existing implementation models resulted in a more accurate picture of actual policy processes. Research conclusions thus included a new theoretical model for assessing policy implementation effectiveness in the region (Fischer-Smith Policy Implementation Measurement for Post-Soviet States). For theoreticians, this research may inform structural considerations when conducting policy research outside of a pluralist democracy. For practitioners, it may allow for better identification of implementation obstacles, in order to more effectively target mitigation efforts. Ultimately, the new considerations presented in this thesis may inform the wider field of policy implementation studies, both in transition regions and developing nations, as well as in the western pluralist societies where implementation theory originated.