Lord Stephen Woolman was appointed as a Senator of the College of Justice in March 2008. He is a graduate of The University of Aberdeen. Between 1978 and 1987 he was a Lecturer at The University of Edinburgh, where for 3 years he was the Associate Dean of the Law School. In 1987, Lord Woolman was admitted to the Faculty of Advocates. He was Standing Junior Counsel for the Inland Revenue, the Ministry of Defence (Procurement) and the Office of Fair Trading. He took silk in 1998.

From 1999 to 2002, Lord Woolman served as an Advocate Depute. Between 2004 and 2008 he was Keeper of the Advocates Library. Lord Woolman was formerly Chairman of the Scottish Council of Law Reporting, the Bar Mediation Group and the Free Legal Services Unit. He is the author of the leading student textbook on the Scots law of contract and also Deputy Chairman of the Boundary Commission for Scotland.