Finding its roots from the manufacturing industry, substantial literature has buttress the factors required for successful implementation of the Lean Six Sigma (LSS) initiative. However researches shows differences in characteristics in terms of understanding and the acceptability of LSS between different countries, particularly within the divide of Developing and Developed economies. This study was conducted in the manufacturing industries of both countries of Nigeria and the United Kingdom, representing Developing and Developed countries respectively. This research examines stages organizations encounter in their LSS journey, exposing attributes peculiar to each of the cases. Employing a qualitative methodological approach, a thorough case analysis comprising of Eight (8) manufacturing companies and 23 interviewees is seeking to expose attributes per case, as the affect the implementation of the Lean Six Sigma initiative. Findings from this study highlights three (3) main themes of Organizational readiness to LSS, LSS Roll-out plan, and Sustainability of LSS as major factors to be considered in the Lean Six Sigma implementation journey. This research further contributes to the body of knowledge relating to implementation issues faced between companies, as findings could aid LSS practitioners on their journey.