Steele received a Rhodes Scholarship and attended St Edmund Hall, Oxford University, graduating in 1986 with a degree in philosophy, politics, and economics.

Steele practised law with Stewart McKelvey Stirling Scales in Halifax from 1989 to 1993 and was General Counsel to the Nova Scotia Workers Compensation Board from 1993 to 1998.

Steele has done workshops in Montenegro, Bosnia and Herzegovina, Kosovo and the Middle East for the National Democratic Institute for International Affairs.

While in official opposition, Steele served as the NDP's critic for Finance, Environment, Acadian Affairs, Insurance Act, and Treasury and Policy Board.

In September 2014, he released a memoir called What I Learned About Politics: Inside the Rise — and Collapse – of Nova Scotia's NDP Government.