Diana Holloway

Diana is an Associate in Osler’s Employment and Labour group. Diana advises and represents both private and public sector employers on a wide range of issues in labour relations and employment law, including employment contracts and workplace policies, employee terminations, employment standards legislation, human rights and accommodation, occupational health and safety, and collective bargaining matters. She also has a particular focus on workplace harassment issues, workplace mental health issues, workplace investigations, and education law.

As a passionate advocate, Diana routinely represents clients in employment litigation, grievance arbitrations, 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 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.


Areas of Expertise

Representative Work

  • Prior to joining Osler, Diana acted for a significant stakeholder in a complex Coroner’s Inquest about Ontario’s 911 Response Systems

Latest Insights

  • Webinar Jun 28, 2023

    Employment and Labour Law Insights: June 2023

    Join us for our webinar series, Employment and Labour Law Insights. Staying informed on the latest developments in this area of law is critical for...

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    Employment and Labour Law Insights: June 2023
  • Webinar Sep 21, 2022

    Employment and Labour Law Insights: Restrictive covenants; electronic monitoring; vaccination policy case law; Maynard v. Johnson ControlsCanada

    Available on-demand, this 60 minute session will provide an update on recent court decisions related to Labour and Employment, as well as pending and...

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    Employment and Labour Law Insights: Restrictive covenants; electronic monitoring; vaccination policy case law; Maynard v. Johnson ControlsCanada
  • Osler Update May 12, 2022

    Accessibility with a plan: new accessibility regulations in British Columbia and Manitoba

    New regulations in British Columbia and Manitoba aim to promote equal participation in employment and public services for individuals with...

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  • Blog Jun 29, 2020

    The Ontario Court of Appeal’s latest decision striking down attempts to control severance cost

    A key way employers control severance cost risk is to hire employees under written employment contracts that specifically limit what the...

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View all Insights

Awards and Recognition

  • Chambers Canada: Canada’s Leading Lawyers for Business: Recognized in Employment & Labour (Ontario)

Speaking and Writing

Speaking Engagements

speaker 28/6/2023
Employment and Labour Law Insights: June 2023
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speaker 21/9/2022
Employment and Labour Law Insights: Restrictive covenants; electronic monitoring; vaccination policy case law; Maynard v. Johnson ControlsCanada
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speaker 18/1/2020
The Changing Workplace: Remote Working and Courts Increasing Severance Costs
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Published Work

  • Speaker, “Liability Issues for Emergency Communicators”, Ontario Fire Association Communicator’s Annual Conference (October 17, 2019)
  • Speaker, “Labour Relations 101”, Ontario Association of Fire Chiefs’ Labour Relations Seminar (January 22, 2019)
  • Speaker, “Bargaining in the Broader Public Sector”, Emergency Services Steering Committee’s Labour Forum (May 25, 2018)

Credentials

Education

  • 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

Languages

  • English
  • French

Professional Affiliations

  • Ontario Bar Association, Executive Member of the Education Law Section
  • Law Society of Ontario