Before coming to the Bar, Desmond worked in the Advice Sector from 1993 until 2003 in a number of organisations including Citizens Advice Bureaux in Clerkenwell, Fulham, Kilburn and Wandsworth, LEAN and Welcare. He became a volunteer at the Free Representation Unit in 1992 and was employed as the Social Security Caseworker in 1995/6. Desmond joined Garden Court Chambers in 2004 (after completing a 12 months pupillage). He was short-listed for Young Legal Aid Barrister of the Year in 2007 for his work in social security.
Desmond advises on welfare benefit decisions that are susceptible to judicial review, including interim payments pending a claim, the refusal to carry out a revision based on official error; the refusal to extend the appeal deadline, the refusal of permission to appeal by an Upper Tribunal Judge and awards of discretionary housing payments.
Desmond accepts instructions to provide written opinions on social security benefits in complex family law proceedings, particularly those involving EU migrants. His written opinion on the income and capital rules for means-tested benefits was described as "very helpful" by the Immigration and Asylum Upper Tribunal in Yarce (adequate maintenance: benefits)Colombia  UKUT 425 (IAC) on the proper approach to be taken.