Now specialising in arbitrations and mediations, Barry comes to those areas after a career as a High Court Judge. Barry spent the first part of his career as a solicitor practicing in the fields of company, commercial, trust and property law. He was a partner in the firm of Tompkins and Wake from 1960 to 1983, at which point he retired to become a barrister sole, specialising in civil litigation particularly in commercial, trust and property matters.

Barry became a silk in 1993. During his time in practice he was a director of many companies including 5 listed on the New Zealand Stock Exchange. He was also a trustee of 3 charitable trusts and 2 superannuation schemes. In 1996 he was appointed a Judge of the High Court and was a member of the Auckland High Court bench until his retirement at the end of 2004. At that time he was a Commercial List Judge and also served a time as Executive Judge in Auckland.

Currently Barry is Chair of the Sports Tribunal of New Zealand, the New Zealand Press Council, Paymark Limited, and the Independent Oversight Group, monitoring Telecom's separation. He is a Fellow of the Arbitrators and Mediators Institute of New Zealand and is on both its Arbitrators and Mediators Panel, and he is a member of the New Zealand Bar Association and the Institute of Directors.

He has had a significant involvement with New Zealand Cricket over 3 decades, including roles as board member, Chairman and President.