Bailey graduated with a Bachelor of Arts Honours in Political Science from the University of Victoria in 1973.

That same year, he joined the Canadian Department of External Affairs.

[1] Throughout his career, Bailey held several notable positions both in Canada and abroad.

His assignments included:[1][better source needed] Bailey also held several postings abroad: He served as ambassador to various countries:[2] In January 2012, Bailey was named Special Adviser on Iran and Syria.

He later served as Director General of the Middle East Bureau.