LAWYER PROFILE
Diana Holloway

Diana Holloway

Canada 2026

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Ranked in 1 practice area

About

Provided by Osler, Hoskin & Harcourt LLP

Practice Areas

Diana is known for her practical, strategic approach to complex mandates and works with a broad range of clients, including TikTok, Toronto Hydro, DoorDash, Honeywell Limited, the Human Resources Professionals Association, 1Password, numerous emerging and high-growth technology companies, and various manufacturing/industrial companies.

Diana excels as an advocate; she has a strong aptitude for negotiating successful outcomes for her clients and routinely represents employers in employment disputes, 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 also has a demonstrated track record of winning the confidence of clients and being entrusted to advise on sensitive workplace investigations, contentious executive and founder disputes, complex company restructurings/mass terminations, and day-to-day HR risk mitigation strategies.

Career

Queen’s University, Juris Doctor

University Jean Moulin (Lyon III), Diploma in International and European Business Law

Queen’s University, Bachelor of Arts (Honours) in Politics

Bar Admission: Ontario, 2018

Professional Memberships

Law Society of Ontario

Chambers Review

Provided by Chambers

Chambers Canada Guide

Employment & Labour - Ontario

Associate to watch
Associates to watch

Individual Editorial

Diana Holloway is an associate in Osler, Hoskin & Harcourt's Toronto office, who frequently assists with a wide range of employment mandates.

Ranked Individuals at Osler, Hoskin & Harcourt LLP (199)

Alberta

British Columbia

Nationwide - Canada

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