On 1 July 1981, he was appointed to the High Court at the age of 40, making him the youngest judge to be appointed to the High Court in Singapore. In 1989, he was made Senate Member and Executive committee member of the Singapore Academy of Law. Justice Lai was appointed Chairman of the Legal Education and Studies Committee of the Academy from 19 January 1989 to 28 July 1995, and Chairman of the Professional Affairs Committee, Singapore Academy of Law from 24 July 1993 until his retirement on 6 February 2006. – on his 65th birthday.