Following his undergraduate degree at Aberdeen University, Woolman completed a solicitor’s apprenticeship. He then became a lecturer in law at Edinburgh University (1978 – 87). For three of those years he served as Associate Dean of the law faculty. In 1987 he published Woolman on Contract, now in its sixth edition and edited by Professor Gillian Black.
In the same year he became an advocate at the Scots Bar. Before taking silk in 1998, Woolman was successively ‘standing junior’ to three government departments: the Office of Fair Trading (1991-95), the Ministry of Defence (Procurement Executive) (1995-96), and the Inland Revenue in Scotland (1996-98).
Woolman was the Keeper of the Advocates Library from 2004 – 08. That gave him certain responsibilities for Sir Walter Scott’s library at Abbotsford. During the same period he was a trustee of the National Library of Scotland, chairman of the Bar’s Free Legal Services Unit, and chairman of the Mediation and Dispute Resolution Group.
Stephen Woolman became a Senator of the College of Justice in 2008. As an Outer House judge he heard both criminal and civil cases. For five years he sat in the commercial court. He was also the Deputy Chairman of the Boundary Commission for Scotland, which designs constituencies for the Westminster and Holyrood parliaments. He chaired the Judicial Institute for Scotland, which is responsible for the education and training of all Scottish judges
Woolman holds an honorary LLD degree from Aberdeen University.