Conroy was born and raised in Beaches-East York, where he attended St. Denis elementary school and Cardinal Newman Secondary School. In 1988, he led an unsuccessful attempt to stop the Newman board from mandating school uniforms ("Toronto Star", 7 June 1988). After completing an Honours degree in History and Political Science at the University of Western Ontario, he worked in Ottawa for four years as an executive and legislative assistant to Liberal Member of Parliament (MP) Tom Wappel in Ottawa.[https://web.archive.org/web/20030705065459/http://www.parl.gc.ca/committees/jula/evidence/178_95-10-24/jula178_blk101.html] He then returned to Beaches-East York to start a family and pursue a career in business. Conroy and his wife Shelley have three children: twin daughters Alexandra and Elizabeth and son Jacob. They are homeowners in the Upper Beach area.