Erin Cowling on small firms, AI, and the freelance edge

Erin Cowling on small firms, AI, and the freelance edge

Small and mid-size firms head into 2026 with one advantage their larger competitors can't easily match — the speed to adopt technology, keep what works, and drop what doesn't. In this episode, Tim Wilbur, managing editor of Canadian Lawyer, talks with Erin Cowling, CEO and founder of Flex Legal Network and a former Bay Street litigator, about what's actually changing for small firms and what just looks like noise. Cowling explains how she built a freelance practice into a network of more than 80 lawyers, paralegals, and law clerks, and why she thinks the firms that are pulling ahead treat their practices as businesses first. The conversation covers clients running their invoices through AI to test whether a bill is fair, the wide split between firms that go all-in on AI and those that refuse to touch it, and the "shiny object syndrome" that leads firms to overspend on tools they barely use. Cowling also pushes back on the idea that freelance counsel are junior help and describes the emerging bottleneck: as associates move faster with AI, senior review still can't be automated. Cowling will appear on the panel, "Running a Small Firm in 2026: What's Changing — and What Actually Matters," at the Canadian Legal Summit this October in Toronto. Register here for the Canadian Legal Summit: https://events.canadianlawyermag.com/canadian-legal-summit?utm_source=newsletter&utm_medium=editorial_article&utm_campaign=CLS2026&utm_content=awareness&utm_term=asset01

Matthew Peters on the AI tools McCarthy Tétrault's lawyers are actually using right now

Matthew Peters, partner and national leader of transformation at McCarthy Tétrault LLP, joins Canadian Lawyer managing editor Tim Wilbur to talk about what AI adoption actually looks like inside one of Canada's largest law firms. Peters revisits predictions he made in a 2017 Canadian Lawyer cover story — and explains why his advice has changed. He walks through how the firm manages workflows across multiple AI platforms, the strategic risks of legal technology vendors becoming competitors, what MT❯Forge is designed to do, and why McCarthy Tétrault is co-developing a course with Western Law to address a breakdown in how junior lawyers learn their craft.

Harvey Brownstone: Canada's first openly gay judge speaks without prejudice

Harvey Brownstone made history in March 1995 when he became the first openly gay judge in Canada. Twenty-six years later, he retired from the Ontario Court of Justice – and he's now free to say exactly what he thinks about the system he served. In this episode, Brownstone speaks with Canadian Lawyer managing editor Tim Wilbur about his new memoir, Without Prejudice: My Life as a Gay Judge (ECW Press, May 2026), tracing a life that spans a French-Algerian Holocaust survivor mother, years on welfare after being thrown out of the house at 19, a career built fighting homophobia, and a 26-year judicial career that included presiding over family and criminal courts, officiating hundreds of same-sex weddings, and a blocked bid for chief justice he describes as "a fiasco." The conversation covers the old boys' club he walked into on his first day on the bench — including colleagues who arranged a lap dance as a form of conversion therapy — and how the judiciary transformed over his tenure. He also makes an unsparing argument about why Canada's family court system is structurally broken: child custody disputes, he says, should be treated as a health care problem, not a legal one, and the adversarial model serves no one — least of all children.

How associates really succeed: a candid conversation with Paul Karvanis

In this episode of the Canadian Lawyer podcast, managing editor Tim Wilbur sits down with Paul Karvanis, former Stikeman Elliott and in-house counsel turned coach, speaker and author of The Successful Associate: From New Lawyer to Making Partner. Drawing on interviews with nearly 50 managing partners, talent leaders and senior lawyers, Karvanis lays out a “hierarchy” of associate success – from delivering quality work reliably, to mastering soft skills, to taking the right level of ownership on files. He explains how the “expectation effect” shapes an associate’s reputation within the firm, why lawyers’ tendency to be hard on themselves can turn useful feedback into a burden, and what both firms and juniors need to change if they want feedback to actually drive improvement. Along the way, he tackles the uncomfortable truth that partnership decisions are driven by firm economics and client mix, and why relentless improvement matters more than early brilliance.

The Human Edge in AI‑Driven M&A: Why Judgment Still Wins Deals

Across Canada, deal activity is being reshaped by AI. Document review, drafting, and diligence are becoming faster and more standardized, but the stakes for clients have never been higher. In this environment, sophisticated buyers, investors, and founders are not paying for paperwork; they are paying for judgment. For corporate and securities practitioners, the real challenge is how to harness AI without losing sight of the human skills that actually move deals forward: judgment, negotiation, and leadership. In this episode of Canadian Lawyer’s podcast series, Pallett Valo LLP partner Mujir Muneeruddin draws on his extensive experience in corporate finance, securities, and M&A to unpack what AI really means for transactional practice. With a background as both a C‑suite public company executive and a deal lawyer, he brings a rare, dual‑lens perspective on how AI is changing workflows, risk allocation, and client expectations and where human insight still makes all the difference. Listeners will learn how to reframe AI not as a replacement for their work, but as a powerful tool that amplifies strategic thinking and client value at every stage of the deal. Tune in to learn: • How AI is commoditizing routine technical work in M&A while leaving accountability, judgment, and leadership squarely with the lawyer. • Why clients ultimately pay for strategic navigation of complexity; managing leverage, timing, personalities, and outcomes rather than for perfectly drafted documents. • How the most effective negotiators treat deals as an information game, focusing on incentives, constraints, and what parties truly care about instead of arguing over positions. • In what ways AI can be a powerful ally for lawyers who lead, think creatively, and communicate clearly and a real threat to those who only execute instructions. • Practical ways ambitious lawyers can build emotional intelligence and deal‑making skills while using AI to quickly close technical knowledge gaps. Listen now to this Canadian Lawyer episode and rethink how you approach M&A in the AI era.