Leonard Dilbert joined the Cayman Islands Government in 1978 as Labour Officer, and until 1995 served in a variety of positions and Departments, rising to the post of Permanent Secretary (now Chief Officer) in 1992.

Between 1995 and 2005 he completed a Diploma in Legal Studies, worked as an independent consultant, did formal studies in poetry and produced a collection of poems, as well as provided voluntary services to both Government and NGOs.

He rejoined the public sector in 2005 as Deputy Director of the Cayman Islands National Museum, and has since served in several Ministries, where he played a leading role in the development of major initiatives such as the NALC, Public Health Review and the Jubilee Park. His last substantive post was that of Senior Strategic Advisor to the Premier, although he has spent much time over the past several years acting as Chief Officer in both the Ministry of Health and the Ministry of Tourism & Development. Throughout his career Mr. Dilbert has made substantial contributions to the development of legislation, policy reforms and institution-building across the Government.

In addition to a diploma in Legal Studies, Leonard holds a Bachelor of Arts (Summa Cum Laude) in Political Science from McMaster University, a Master of Arts in Political Science from the University of Western Ontario, and a Master of Science in Social Policy and Planning from the London School of Economics. He has also worked towards a Masters in Fine Arts at Vermont College.

Leonard Dilbert is married to Jennifer; they have two daughters, two sons-in-law, a granddaughter, Elizabeth and a grandson, Alexander.