Diana Holloway

Diana Holloway

Associate, Employment and Labour

Contact Information


tel: 416.862.6641



Areas of Expertise

Bar Admission

Ontario, 2018


  • 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


English, French

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.

  • Daylight Automation

    Daylight Automation in its acquisition by Quadient

  • Verisk Analytics

    Verisk Analytics in its acquisition of Opta

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

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

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


  • 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)