Taking the opportunity to unpack conversations from Legalweek New York in March, Caroline Hill and Ari Kaplan regroup in their Charting Change in Legal podcast, noting that this year’s event felt less like business as usual and more like a moment of genuine transition for the legal industry.
As always the conversation ranges widely, from the realities of AI adoption and ROI, to the future of client relationships, orchestration, data foundations, and what law firms can now do that was previously impossible. Along the way, Hill and Kaplan reflect on packed sessions, provocative “hot takes”, and a palpable shift in tone: less fear, more pragmatism, and a growing acceptance that the way law is practised is fundamentally changing.
A central theme is maturity. As Kaplan puts it, the industry is past the stage of speculating about what AI might do and is now grappling with how to extract real value across practice, business development, finance and client service. Hill draws on insights from her Legal IT Insider breakfast at Legal Week to explore whether client relationships will still matter in a data‑driven future, or whether efficiency alone will become the differentiator. The answer, unsurprisingly, is more nuanced—and more challenging—than either extreme.
The discussion also digs into the growing importance of orchestration: the people and processes that sit between tools, data and practice groups, helping firms navigate an increasingly complex technology landscape. Data quality, governance and consolidation emerge as critical enablers, particularly as firms contend with mergers, mobility and fragmented systems.
One standout moment comes with a quote from Oz Benamram (formerly White & Case and Simpson Thacher), which reframes the AI debate entirely: instead of asking how to keep up with AI, firms should be asking what they can now offer that was genuinely impossible before. It’s a question that cuts through adoption theatre and goes to the heart of value creation.
For anyone trying to make sense of where legal tech is heading post‑Legal Week—and what actually matters amid the noise—this episode offers a thoughtful, grounded and occasionally provocative conversation between two long‑time observers of the market.
You can listen to the full episode on Spotify or watch the full episode on YouTube below:
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