Woolman was educated at George Heriot's School, Edinburgh[3] and studied law at the University of Aberdeen.

He was a lecturer in the Faculty of Law of the University of Edinburgh from 1978 to 1987, serving as Associate Dean from 1981 to 1984.

He published the first edition of his work on Contract in 1987, being admitted to the Faculty of Advocates the same year.

[4][5] Woolman served as Standing Junior Counsel to the Office of Fair Trading (1991 to 1995), the Procurement Executive of the Ministry of Defence (1991 to 1995), and the Inland Revenue (1996 to 1998).

He holds an honorary LLD from the University of Aberdeen[8] and was elected as a fellow of the Royal Society of Edinburgh in 2022.