Our Team

Simon Chester is a partner in the Litigation and Business Law groups of Heenan Blaikie’s Toronto office, with special focus on conflicts of interest, professional responsibility, and legal opinions. He has been a pioneer for the last twenty five years in the application of advanced technologies to the practice of law.

Educated at Oxford University, (B.A., M.A.) and Osgoode Hall Law School, (LL.M.), he is professionally qualified in Ontario (1982) and England and Wales (1988). 

Simon has held leadership positions in professional organizations and was the first non-American to chair the American Bar Association’s Tech Show. He chairs the ABA Law Practice Management Section’s Editorial Advisory Board, the LPMS Education Board and its New Media and Internet Board. He served as President of the College of Law Practice Management and as President of the Oxford University Society in Toronto; he is a director of the Canadian Rhodes Scholars Foundation. He is also Fellow of the College of Law Practice Management.

Simon has often testified before House of Commons and Senate Committees and has contributed articles to the American Lawyer, International Business Lawyer, International Financial Law Review, Law Practice Management, CAMagazine, CBA National, Business Law International and the ABA Journal. He has written chapters for Winning with Technology, The Quality Pursuit, Environmental Rights in Canada and Canadian Legal Practice.

He has spoken on law, technology and professional issues to audiences across Canada, the United States, Mexico, Scotland, England, Belgium, the Netherlands, India and Singapore. Recent presentations include Proof of Foreign Law – Canadian Perspectives, The European Commission Directorate-General Justice, Directorate A, and The Hague Conference on Private International Law, Conference on: Access to Foreign Law in Civil and Commercial Matters (2012); Spinning the Web – Social Media and Ethics in the Practice of Law (The Commons Institute, Expert Sessions on Practice Management 2012); Avoiding the Doghouse - The Ten Mistakes that Give Rise to Most Malpractice Claims (The Commons Institute, Expert Sessions on Practice Management 2012); Emerging Issues in Social Media (Pacific Legal Technology Conference 2011); Risks, Security and Ethics in the Cloud (Pacific Legal Technology Conference 2011); New Developments in the English and Indian Legal Professions (College of Law Practice Management, 2011); Ten things that US business lawyers should understand about Canadian Law and Commercial Opinion Practice (ABA Business Law Section, 2011); Twenty-Five Years of TechShow (ABA 2011); Towards a New Profession (Federation of Law Societies of Canada , 2010); The Challenge of Social Media for the Ethical Practice of Law (ABA Legal Malpractice Conference, Washington D.C., 2010); The New Privacy Agenda (Law Society of Upper Canada, 2010); Conflicts and Access to Justice (International Legal Ethics Conference, Stanford University, 2010); A Sea Change in England – the Legal Services Act, 2007 (College of Law Practice Management, American University, Washington D.C., 2010); Social Media and the Courts (Supreme Court of Canada, Ottawa, 2010), Les médias sociaux comme moyen d'accès à l'information juridique (Educaloi, Dire le droit pour être compris, Montréal, 2010); and New York State Bar Association, Presidential Summit, The Future of the Legal Profession, 2011.

He has advised both the Canadian Bar Association and the International Bar Association on professional issues; he co-leads the most successful Canadian legal blog http://www.slaw.ca. He was recently awarded the first Chief Justice of Ontario Fellowship in Legal Ethics and Professionalism.

He is AV^® Preeminent^TM Peer Review Rated by Martindale-Hubbell, the highest peer review rating awarded to a lawyer for his legal skills and sense of ethics.