CL Talk

How law firms are rethinking talent retention for the next generation of lawyers

Dec 02, 2025

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.