Diana Holloway

Diana Holloway

Associate, Employment and Labour

Toronto

(416) 862-6641 

[email protected]

Bar Admission: Ontario, 2018

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Areas of Expertise

Employment and Labour

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.

Areas of Expertise

Employment and Labour

Representative Work

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

Awards and Recognition

  • Recognized as an “Associate to Watch” in Employment & Labour (Ontario)

    —Chambers Canada

  • Recognized as “One to Watch” in Labour and Employment Law

    —Best Lawyers in Canada

Community Involvement

  • Project Work (non-profit supporting persons with intellectual disabilities to obtain meaningful employment and helping to build inclusive workplaces), Member of the Board of Directors

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

  • Law Society of Ontario

Osler is a leading business law firm practising internationally from offices across Canada and in New York. Our clients include industry and business leaders in all segments of the market and at various stages in the growth of their businesses. We have built our reputation on our commitment to our clients' success and the experience, expertise and collaborative approach for which we are recognized. We believe that our success is a reflection of our clients' success.