Toby graduated in Law from Durham University (Grey College) in 1972. He was Called to the Bar by Inner Temple in 1973. From 1974, after pupillage, he practised as a Barrister in London (latterly as a QC) in civil liability claims and employment and discrimination claims. He was also involved with the Bar Council and with Inner Temple Advocacy Training.
He was appointed a Circuit Judge in 2007, deployed to the Cities of Worcester and Hereford, trying criminal, family and civil claims. He was Honorary Recorder of the City of Hereford 2009-2016. He was a judge member of the Parole Board 2010–13.
He retired in 2016. He is a Bencher (Governor) of Inner Temple, with particular interest in Outreach and Scholarships. He has been Vice-Chair of Heart of Mercia Multi-Academy Trust (Sixth Form Colleges and some secondary schools in Herefordshire and Worcestershire). He is an Honorary Fellow of the University of Worcester, and an Honorary Freeman of the City of Hereford.