About Diana

Diana Holloway is an associate practising employment and labour law, advising public and private sector clients on high-risk terminations, sensitive workplace investigations, human rights and accommodation matters, workforce restructurings, and other labour issues, along with day-to-day HR risk management. She represents employers in employment disputes and litigation, grievance arbitrations, and collective bargaining, appearing before civil courts, the Human Rights Tribunal of Ontario, the Ontario Labour Relations Board, and the Ministry of Labour. Holloway was named an "Associate to Watch" in Employment & Labour by the Chambers Canada Guide in both 2024 and 2025. She joined Osler as an associate in 2020, having previously articled and worked at a boutique employment and labour firm.

Practice areas

Employment & Labour Law

Education & credentials

Law school
Queen's University

Listing compiled from public sources in July 2026. Confirm Diana Holloway’s licence and standing in the Law Society of Ontario directory ↗