Since early 2005, members of the NUS Legal Skills Team have been engaged in a project jointly sponsored by the UNDP and the Singapore government to translate Lao laws into English. The translations have been adopted by the National Assembly of Laos, published online and made easily available with the aim of facilitating interaction between the international community and Laos. At this time, the team has already worked on more than three quarters of the total number of laws in Laos. This paper discusses the challenges faced by the project team and the insights gained in bridging the differences of language, legal system and culture. The author hopes that the insights will be relevant not just to those engaged in the process of legal translation but to transactional lawyers, law academics and other readers who have had to confront similar challenges in arriving at a true meeting of minds across legal systems and cultures