In this episode, iGaming Ontario President and CEO Joseph Hillier discusses how Ontario has built a competitive online gambling market designed to draw players away from unregulated sites while maintaining strong safeguards in place. He traces his path from Bay Street to the Ministry of the Attorney General and the Alcohol and Gaming Commission, explaining how this mix of private practice, banking, and public service now shapes his approach to regulation. Hillier discusses his priorities at iGaming Ontario, including treating operators as business partners, strengthening responsible gambling tools such as self-exclusion, modernizing anti-money laundering systems and preparing for emerging issues like cross-border pooled play and digital currencies.

Toronto criminal defence lawyer Robert Kivlichan joins CL Talk to share how his addiction and severe panic attacks collided with a Law Society of Ontario spot audit and led to his suspension and a capacity investigation. He describes why he believes the LSO’s process can weaponize mental health disclosures, forcing lawyers to surrender sensitive medical information to non‑medical staff, even while they are in treatment. Kivlichan also explains the path he took to lasting sobriety, how he rebuilt his practice, and the hard advice he now gives to lawyers, regulators, and families about supporting professionals in crisis.

In this episode of CL Talk, recorded live at the Canadian Legal Summit, host Robert De Toni moderates a candid conversation with firm leaders Kurt Schlachter of Stringam, Jacqueline Dinsmore of Caravel Law and boutique founder Ashlee Froese on what it really takes to keep today’s lawyers. The panel delves into why younger lawyers are no longer motivated solely by partnership, how culture plans, “success plans,” and flexible budgets can replace vague promises, and why flexible work arrangements must be genuine rather than merely policy rhetoric. They also tackle the mental health impact of the billable hour, the role of a “director of lawyer happiness,” the rise of reverse mentorship in an AI-enabled practice, and the hard business realities around portable books of business, equity buy-ins and alternative career paths beyond the traditional ladder.

Danielle Robitaille, Managing Partner of the Year at the 2025 Canadian Law Awards, sits down to discuss her path from litigator to firm leadership at Henein Hutchison Robitaille LLP. She shares how her focus on mentorship, mental health support, and inclusive recruitment has shaped a thriving legal practice handling high-stakes litigation and white-collar investigations. From training partners on actionable feedback to pioneering direct access to counselling for associates, Robitaille reveals the practical strategies behind building a strong firm culture. If you know a lawyer or law firm making a meaningful impact in your community, nominations for the 2026 Canadian Law Awards are now open through January 30, 2026 – consider recognizing their contributions. Visit www.lawawards.ca to nominate.

In this episode, Tim Wilbur sits down with Canadian entrepreneur Jody Glidden, founder and CEO of Postilize, to discuss how artificial intelligence is changing client engagement in the legal sector. Glidden talks about the evolution from traditional CRM to proactive relationship management, the challenges law firms face with data, and how AI can help lawyers anticipate client needs and manage business development more efficiently. Postilize is used by major law firms in the US.

In this episode, Sylvie Rodrigue, partner at Torys LLP and national class action leader, shares how overcoming personal and professional hurdles shaped her legal career. Rodrigue discusses the strategies that helped her navigate new markets, the value of finding champions, and the importance of building both personal resilience and professional expertise. She also reflects on her experiences with imposter syndrome, the role of balance in her life, and the insights behind her new book, offering practical advice for anyone forging their own path in law and beyond.

In this episode, recorded live at the Canadian Legal Summit, Faren Bogach of Construct Legal and Paul Saunders of Stewart McKelvey join moderator Jacquelyn Stevens to dissect how law firm compensation models are evolving under pressure from clients and shifting lawyer expectations. The panellists share firsthand experiences overhauling traditional pay structures, from Construct Legal’s radically transparent profit-sharing approach to Stewart McKelvey’s strategic, metrics-driven overhaul. They reveal how these changes have impacted recruitment, retention, collaboration, and firm culture, offering candid insights into what works – and what doesn’t – when law firms challenge the status quo on compensation.

Gabe Pereyra, president and co-founder of Harvey, talks about the company’s rapid growth, its expansion into Canada, and how AI is reshaping the legal industry. He explains why Harvey chose Toronto as a key hub, how the company is building out its local teams, and what sets its technology apart in a crowded legal tech market. Pereyra also discusses the challenges of localizing AI tools for Canadian law firms, the evolving relationship between lawyers and technology, and why he believes the future of legal work will demand even greater expertise – supported by smarter, more integrated tools.

Ed Carmichael, managing lawyer at OwnRight, a Toronto-based digital platform for real estate transactions, speaks about the urgent need for greater transparency and stronger oversight in Ontario’s real estate sector. Drawing on the recent iPro trust account shortfall, he outlines how gaps in regulatory audits and outdated industry practices leave both clients and lawyers vulnerable. Carmichael also discusses how technology can address these risks by providing real-time updates and clarity throughout the transaction process.

Kirsti McHenry, Pro Bono Ontario’s executive director, speaks about the organization’s rapid expansion in response to surging demand for free legal help, the impact of technology on service delivery, and the critical role of structured pro bono programs in law firms. She highlights how global events and economic shifts are driving new legal challenges for Ontarians, the importance of partnerships with legal tech innovators and community groups, and the need for more lawyers to get involved. McHenry also discusses how streamlined volunteer opportunities, such as the legal advice hotline and sponsor days, are making it easier for busy professionals to contribute meaningfully to access to justice across the province.

In this episode, Sandeep Tatla speaks about why open dialogue and psychological safety are essential for meaningful progress in diversity, equity, and inclusion (DEI) within law firms. She explains why policing and cancel culture undermine DEI efforts, and shares practical strategies for building trust and fostering inclusion in legal workplaces. Drawing on her experience as a global DEI leader, Tatla highlights the importance of intentional leadership and daily actions over one-off programs. Tatla will participate in a panel and interactive discussion on the evolving approach to DEI in Canada at the upcoming Canadian Legal Summit on October 9 in Toronto. For more information about the summit, visit https://www.canadianlawyermag.com/events

On this episode, Steven Ngo, senior counsel at Rivian and co-founder of Beyond the A, joins us to discuss how fatherhood, legal innovation, and mental health advocacy have shaped his career and outlook. Ngo shares candid insights on breaking barriers in the legal profession, navigating complex regulatory challenges at Rivian, and why honest conversations—whether in a car or a boardroom—matter more than ever. Listen to more of Steven’s conversations on fatherhood and ambition at https://www.2dads1car.com/

Christy Elliott, Senior Vice President, Sustainability, External Affairs and General Counsel at Keyera, shares her insights on the evolving role of the general counsel and the intersection of legal leadership with business strategy in Canada’s energy sector. Elliott will be featured in a roundtable discussion at the Canadian Legal Summit on October 9 in Toronto, where she will join other leaders for a session entitled “Future GC playbook: Essential skills to build a business mindset.” Visit https://www.canadianlawyermag.com/events for more information about the summit.

Derrick Li, chief operating officer at Lawson Lundell, speaks about building a clear and actionable AI strategy for law firms. Drawing on his experience leading digital transformation, Li discusses aligning technology with client needs and explains how Lawson Lundell is navigating the challenges and opportunities of artificial intelligence. He offers insights on governance, change management, and the future of legal tech – essential listening for legal professionals considering their next steps in AI adoption.

Mark Longo – managing partner of Osler’s Vancouver office and co-chair of the firm’s emerging and high-growth companies group – discusses the remarkable evolution of British Columbia’s technology sector. Longo shares insights on the rise of unicorn companies, the shifting legal landscape, and how Osler is adapting to meet the changing needs of tech clients in a fast-paced, increasingly global market.

Stephanie Leung, senior legal counsel at Enbridge, shared her perspective on the evolving role of in-house counsel, the importance of Indigenous partnerships in the energy sector, and the operational and cultural innovations shaping legal teams today. Leung discussed how Enbridge’s approach to collaboration, diversity, and legal operations is redefining expectations for both in-house and external counsel. She also addressed the challenges of navigating market volatility, driving inclusion, and leveraging technology responsibly. Leung will speak on these topics at the Canadian Legal Summit 2025 in Toronto on October 9. Visit https://www.canadianlawyermag.com/events for more information about the summit.

Dr. Traci Cipriano, assistant clinical professor in the Department of Psychiatry at Yale School of Medicine and author of The Thriving Lawyer, discussed the urgent need to address burnout in the legal profession, the barriers to meaningful change, and the structural solutions required to support lawyer well-being. Cipriano explored why self-care alone is not enough, the critical role of leadership in driving cultural shifts, and practical policies that can make a real difference in legal workplaces. She will speak on these issues at the Canadian Legal Summit 2025 in Toronto on October 9. Visit https://www.canadianlawyermag.com/events for more information about the summit.

Lucas Kilravey is an associate at Weil, Gotshal & Manges LLP’s real estate practice in New York. He spoke about the business case for diversity in law, the persistent gaps in representation at major firms, and the practical steps needed to support and advance diverse legal talent. Kilravey discussed the impact of open communication and inclusive leadership on team performance, the shortcomings of traditional mentorship programs, and the urgent need for greater transparency and accountability in law firm hiring and promotion practices. Kilravey will speak on these issues at the Canadian Legal Summit 2025 (https://events.canadianlawyermag.com/canadian-legal-summit?utm_source=newsletter&utm_medium=editorial_article&utm_campaign=CLS2025&utm_content=awareness&utm_term=asset01) in Toronto on October 9.

Justice Sheilah Martin has served on the Supreme Court of Canada since 2017, following appointments to the Alberta Court of Queen’s Bench and the Alberta Court of Appeal. Trained in civil and common law, she built her career across academia, private practice and the judiciary, focusing on constitutional law, criminal justice and equality rights. In this episode, Justice Martin discusses the value of legal education, the evolving role of judges, and the responsibility of law to reflect fairness in a country as diverse and complex as Canada. In 2014, she was named one of Canadian Lawyer’s Top 25 Most Influential Lawyers: https://www.canadianlawyermag.com/rankings/the-top-25-most-influential-lawyers-in-canada/387950

Bail reform, judicial appointments, and the balance between public safety and Charter rights are all on the table as Canada’s new justice minister takes office. Fraser talks to Canadian Lawyer about how a direct appeal from Prime Minister Mark Carney led him to return to politics after announcing his departure.