CL Talk

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

Jun 02, 2026

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.