Friends Who Argue

This episode of the podcast, hosted by Eric Sherkin, a partner at Miller Thomson LLP in Toronto, features a discussion about business development for litigators, with lawyer and career coach Jane Southren and Kelly Osaka, a partner at Dentons LLP in Calgary. The conversation explores mindset shifts needed to effectively transition from associate to partner, relationship-building techniques, and practical tips for balancing business development with other professional and personal responsibilities. Listeners will gain insights into leveraging modern tools, creating personalized approaches, and building sustainable practices in today’s evolving legal landscape. Eric Sherkin [https://www.millerthomson.com/en/your-team/eric-sherkin/] is a commercial litigation lawyer at Miller Thomson, with broad experience across many areas of practice, and a particular focus on creditors’ remedies and contract disputes. He has appeared at all levels of court in Ontario, has extensive experience with injunctions, and maintains a growing practice in property tax assessment appeals under the Assessment Act. Eric has been recognized as a “Future Star” by Benchmark Litigation since 2022 and a Thomson Reuters “Standout Lawyer” since 2023. He is an active member of his community and currently serves on The Advocates’ Society’s Mid-Career Advocates Standing Committee (MASC). Jane Southren [https://www.southren.ca/teambios] is the Founder of Southren Group Inc. (SGI), a coaching and consulting firm that empowers lawyers and law firms to build sustainable, fulfilling practices. With nearly 30 years of experience as a litigator, business development leader, and executive coach, Jane brings rare insight into the human side of legal success. At SGI, she leads programs that blend behavioural science, strategy, and real-world application—helping lawyers align their practices with their values, relationships, and goals. Known for inspiring confidence and sparking growth, Jane's mission is to help people think, be, and do better - professionally and personally. Kelly Osaka [https://www.dentons.com/en/kelly-osaka] is a Partner at Dentons in Calgary in the Litigation and Dispute Resolution group, the Privacy and Cybersecurity group, and co-lead of the Privacy Litigation subgroup. Kelly is known for her expertise in complex commercial litigation, with a focus on class action defence, securities litigation, shareholder disputes, plans of arrangement, ESG and greenwashing risks and navigating governance best practices. Kelly is a trusted leader in privacy and cybersecurity, providing practical solutions in a rapidly evolving landscape. She is a frequent speaker and writer on litigation and privacy topics, offering practical, business-focused legal solutions. Land Acknowledgement The Advocates’ Society acknowledges that our offices, located in Toronto, are on the customary and traditional lands of the Mississaugas of the Credit, the Haudenosaunee, the Anishinabek, the Huron-Wendat and now home to many First Nations, Inuit, and Metis peoples.  We acknowledge current treaty holders, the Mississaugas of the Credit and honour their long history of welcoming many nations to this territory. While The Advocates’ Society is based in Toronto, we are a national organization with Directors and members located across Canada in the treaty and traditional territories of many Indigenous Peoples. We encourage our members to reflect upon their relationships with the Indigenous Peoples in these territories, and the history of the land on which they live and work. We acknowledge the devastating impacts of colonization, including the history of residential schools, for many Indigenous peoples, families, and communities and commit to fostering diversity, equity, and inclusiveness in an informed legal profession in Canada and within The Advocates’ Society.

In the second part of this two-part series, the Honourable Patrick Boyle continues his conversation with Justin Kutyan, National Leader of the Tax Litigation group at KPMG Law LLP, to discuss Patrick’s reflections from serving as a judge on the Tax Court of Canada for 17 years. In episode two, Patrick shares what he found to be effective (or not effective) advocacy from counsel, discusses different litigation styles, provides tips for litigators to consider, and closes with his thoughts on the future of the Tax Court. The former Justice Boyle [https://kpmg.com/ca/en/home/contacts/b/patrick-boyle.html] is Of Counsel with KPMG Law. Prior to joining KPMG Law, Patrick served as a Justice of the Tax Court of Canada for over 17 years, and he previously worked with a large national law firm in Toronto and Ottawa for 25 years. He holds common law and civil law degrees and is bilingual. On the Tax Court, he presided over English and French appeals, served as Acting Associate Chief Justice, Education Committee Chair, and member of the Rules Committee. Prior to his judicial appointment, Patrick’s practice focused on financial institutions, services and transactions, corporate and commercial transactions, and the taxation and regulation of charities and not-for-profits. He litigated cases in the Tax Court, the Federal Court and the Federal Court of Appeal. He also taught Advanced Tax at University of Windsor Law School, was on secondment for two years at the Tax Policy Branch of the Department of Finance as Special Advisor to the Assistant Deputy Minister. Justin Kutyan [https://kpmg.com/ca/en/home/contacts/k/justin-kutyan.html] specializes in litigating tax cases and leads KPMG Law’s National Tax Litigation team. He has extensive experience in trial advocacy, and is well-versed in strategic and tactical courtroom skills that can help to win at trial or produce favourable settlements. Justin has successfully resolved disputes involving a wide range of income tax, GST/HST, and customs issues. Over the course of his career, Justin has appeared before the Tax Court of Canada, Canadian International Trade Tribunal, Ontario Superior Court of Justice, Federal Court, and Federal Court of Appeal. He has also assisted on cases before the Supreme Court of Canada. He also advises on all other stages in the dispute process, and has familiarity navigating the audit and appeals process with Canada Revenue Agency. Land Acknowledgement The Advocates’ Society acknowledges that our offices, located in Toronto, are on the customary and traditional lands of the Mississaugas of the Credit, the Haudenosaunee, the Anishinabek, the Huron-Wendat and now home to many First Nations, Inuit, and Metis peoples.  We acknowledge current treaty holders, the Mississaugas of the Credit and honour their long history of welcoming many nations to this territory. While The Advocates’ Society is based in Toronto, we are a national organization with Directors and members located across Canada in the treaty and traditional territories of many Indigenous Peoples. We encourage our members to reflect upon their relationships with the Indigenous Peoples in these territories, and the history of the land on which they live and work. We acknowledge the devastating impacts of colonization, including the history of residential schools, for many Indigenous peoples, families, and communities and commit to fostering diversity, equity, and inclusiveness in an informed legal profession in Canada and within The Advocates’ Society.

In the first episode of this two-part series, the Honourable Patrick Boyle sits down with Justin Kutyan, National Leader of the Tax Litigation group at KPMG Law LLP to discuss Patrick’s reflections from serving as a judge on the Tax Court of Canada for 17 years. In episode one, Patrick shares what it was like to get the phone call appointing him to the Court and the lifestyle differences moving from private practice on Bay Street to serving on the bench. He also explains how the Tax Court fits within Canada’s legal systems and aspects of the Tax Court that are unique or different from other courts. The former Justice Boyle [https://kpmg.com/ca/en/home/contacts/b/patrick-boyle.html] is Of Counsel with KPMG Law. Prior to joining KPMG Law, Patrick served as a Justice of the Tax Court of Canada for over 17 years, and he previously worked with a large national law firm in Toronto and Ottawa for 25 years. He holds common law and civil law degrees and is bilingual. On the Tax Court, he presided over English and French appeals, served as Acting Associate Chief Justice, Education Committee Chair, and member of the Rules Committee. Prior to his judicial appointment, Patrick’s practice focused on financial institutions, services and transactions, corporate and commercial transactions, and the taxation and regulation of charities and not-for-profits. He litigated cases in the Tax Court, the Federal Court and the Federal Court of Appeal. He also taught Advanced Tax at University of Windsor Law School, was on secondment for two years at the Tax Policy Branch of the Department of Finance as Special Advisor to the Assistant Deputy Minister. Justin Kutyan [https://kpmg.com/ca/en/home/contacts/k/justin-kutyan.html] specializes in litigating tax cases and leads KPMG Law’s National Tax Litigation team. He has extensive experience in trial advocacy, and is well-versed in strategic and tactical courtroom skills that can help to win at trial or produce favourable settlements. Justin has successfully resolved disputes involving a wide range of income tax, GST/HST, and customs issues. Over the course of his career, Justin has appeared before the Tax Court of Canada, Canadian International Trade Tribunal, Ontario Superior Court of Justice, Federal Court, and Federal Court of Appeal. He has also assisted on cases before the Supreme Court of Canada. He also advises on all other stages in the dispute process, and has familiarity navigating the audit and appeals process with Canada Revenue Agency. Land Acknowledgement The Advocates’ Society acknowledges that our offices, located in Toronto, are on the customary and traditional lands of the Mississaugas of the Credit, the Haudenosaunee, the Anishinabek, the Huron-Wendat and now home to many First Nations, Inuit, and Metis peoples.  We acknowledge current treaty holders, the Mississaugas of the Credit and honour their long history of welcoming many nations to this territory. While The Advocates’ Society is based in Toronto, we are a national organization with Directors and members located across Canada in the treaty and traditional territories of many Indigenous Peoples. We encourage our members to reflect upon their relationships with the Indigenous Peoples in these territories, and the history of the land on which they live and work. We acknowledge the devastating impacts of colonization, including the history of residential schools, for many Indigenous peoples, families, and communities and commit to fostering diversity, equity, and inclusiveness in an informed legal profession in Canada and within The Advocates’ Society.

This episode of Friends Who Argue features a discussion panel with three lawyers who have made the transition from BigLaw to found very different types of small or solo legal practices. Our speakers include Alexi Wood, Ryan Breedan, and John McIntyre. Our panelists discuss the very different reasons why they decided to found an independent legal practice, the myths and misconceptions of starting a small law practice, what challenges they overcame, and why they value the freedom of small or solo practice. Alexi Wood [https://www.stlbarristers.ca/alexi-wood] graduated law school in 2000 and started out carrying out non-private practice work relating to international development and the Canadian Civil Liberties Association. Alexi transitioned to BigLaw six or seven years after law school, and valued the commercial litigation training she received working in BigLaw for the decade that followed. Alexi struck out to found a law practice that was more flexible, diverse, and responsive to a mission statement that she could champion (as well as to benefit from conflict of interest referrals). Ryan Breedon [https://breedon.ca/about/ryan-breedon/] made partner at a “big” Bay Street litigation boutique and was essentially content with his career. However, circa 2015 his wife and him wanted to relocate their young family back to Barrie, Ontario, where they had roots. Remote working was not yet a thing that law firms did at this time, which led Ryan to found his own solo practice. This eventually led to hiring some associate or two, and, recently, a partnership. While not his purpose, Ryan very much valued the flexibility and ability to make independent decisions that being a solo/small practitioner provided him. John McIntrye [https://www.mcintyre-szabo.com/] gained valuable experience in the health law specialty while articling and being an associate in BigLaw. John began to feel increasingly constrained by the bureaucratic environment he was in. He therefore left legal practice to pursue a master of public health at John Hopkins in the United States, intending to continue his career in the health sector but not necessarily legal practice. With the pandemic having very much put remote work on the table, John initially carried out Canadian health law work as something of a side practice while in graduate studies. In 2022, however, he joined forces with Jessica Szabo and embarked on a business development spree to found a boutique health law firm. This was successful, although a growing business leads to its own challenges.  Land Acknowledgement The Advocates’ Society acknowledges that our offices, located in Toronto, are on the customary and traditional lands of the Mississaugas of the Credit, the Haudenosaunee, the Anishinabek, the Huron-Wendat and now home to many First Nations, Inuit, and Metis peoples.  We acknowledge current treaty holders, the Mississaugas of the Credit and honour their long history of welcoming many nations to this territory.   While The Advocates’ Society is based in Toronto, we are a national organization with Directors and members located across Canada in the treaty and traditional territories of many Indigenous Peoples. We encourage our members to reflect upon their relationships with the Indigenous Peoples in these territories, and the history of the land on which they live and work.   We acknowledge the devastating impacts of colonization, including the history of residential schools, for many Indigenous peoples, families, and communities and commit to fostering diversity, equity, and inclusiveness in an informed legal profession in Canada and within The Advocates’ Society.

This episode of Friends Who Argue marks our first French episode, as we are discussing mentoring with TAS’ Quebec recipient of the Excellence in Mentoring Award, Julie Chenette. Dans un entretien avec Antoine Veillette, nos deux invités ont l’occasion d’échanger sur ce que la relation de mentorat leur apporte, sur l’identification d’un bon mentor et l’opportunité d’en identifier un au sein de son cabinet ou à l’externe, les principaux conseils pour un mentorat fructueux et certains aspects moins fréquemment discutés du mentorat. Julie Chenette [https://chenette.ca/team/julie-chenette/] est associée fondatrice chez Chenette, boutique de litige. Me Chenette a fondé son cabinet après avoir pratiqué pendant près de 20 ans comme avocate puis comme associée au sein du groupe du litige, des recours collectifs et de la responsabilité professionnelle chez McCarthy Tétrault à Montréal. Avocate renommée en litige de responsabilité professionnelle, diffamation et enquêtes disciplinaires, elle a donné plusieurs conférences dans les domaines du droit de la responsabilité des professionnels et de la déontologie, et a enseigné la procédure et la responsabilité civile à l’École du Barreau du Québec. Me Chenette a reçu en 2024 le prix d’Excellence en mentorat de la Société des plaideurs qui récompense les plaideurs qui ont fait preuve d’un engagement exceptionnel et d’excellence dans le mentorat au Québec. Antoine Veillette [https://langlois.ca/equipe/veillette-antoine/] est avocat chez Langlois. Habitué d’intervenir dans le cadre de litiges complexes en matière civile et commerciale, il exerce principalement en droit de la consommation et de l’environnement ainsi qu’en matière de responsabilité du fabricant. Il est aussi appelé à agir à tout stade de l’instance en matière de faillite et d’insolvabilité. Impliqué auprès de la Société des plaideurs, Me Veillette est à un point de son parcours professionnel où il agit à titre de mentor tout en poursuivant sa propre relation comme mentoré, lui permettant ainsi d’échanger sur ces deux aspects avec Me Chenette. Land Acknowledgement The Advocates’ Society acknowledges that our offices, located in Toronto, are on the customary and traditional lands of the Mississaugas of the Credit, the Haudenosaunee, the Anishinabek, the Huron-Wendat and now home to many First Nations, Inuit, and Metis peoples.  We acknowledge current treaty holders, the Mississaugas of the Credit and honour their long history of welcoming many nations to this territory.   While The Advocates’ Society is based in Toronto, we are a national organization with Directors and members located across Canada in the treaty and traditional territories of many Indigenous Peoples. We encourage our members to reflect upon their relationships with the Indigenous Peoples in these territories, and the history of the land on which they live and work.   We acknowledge the devastating impacts of colonization, including the history of residential schools, for many Indigenous peoples, families, and communities and commit to fostering diversity, equity, and inclusiveness in an informed legal profession in Canada and within The Advocates’ Society.