Probyn was born on 14 May 1951. He received a Bachelor of Arts degree from Queen's University in 1973, and later received a Master of Public Administration from the Kennedy School of Government at Harvard University. He was a policy adviser to Nova Scotia Premier John Buchanan in 1983, and served as a senior policy adviser to the Canadian Minister Energy, Mines and Resources from 1984 to 1986. He established Probyn & Company in 1994 to fund energy projects, and is a member of the Metro Board of Trade and the Albany Club.[https://web.archive.org/web/20051104142510/http://www.newsworld.cbc.ca/election97/ridings/205.html] He has written in defense of the Monarchy in Canada in the national media ("Globe and Mail", 4 October 2000).