Diana Patricia Margaret Holloway

Diana has a broad employment and labour practice and works with a wide range of clients in both the public and private sectors. She is known for her practical, strategic approach to complex mandates and regularly advises employers on high-risk terminations, sensitive workplace investigations, human rights and accommodation issues, workforce restructurings, varied labour matters, and day-to-day HR risk mitigation strategies.

Diana excels as an advocate; she has a strong aptitude for negotiating successful outcomes for her clients and routinely represents employers in employment disputes, employment litigation, grievance arbitrations, collective bargaining, and proceedings in a variety of forums, including civil court, the Human Rights Tribunal of Ontario, the Ontario Labour Relations Board, and the Ministry of Labour.

Diana was recognized in the Chambers Canada Guide as an “Associate to Watch” in Employment & Labour (2024 and 2025).

Diana joined the firm as an associate in 2020, prior to which she articled and was an associate at a pre-eminent employment and labour boutique.

Two years after the Ontario government began a review of the province’s Rules of Civil Procedure, sweeping reforms are expected some time in 2026.

In the second instalment of our quarterly Employment and Labour Law Insights webinar series, Osler’s Kelly O’Ferrall, Steven Dickie, Irmak...