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Stop Piloting: Smarter Paths to Generative AI in Law Firms

By Andy Morris and Don Jaycox and Dan Safran
August 31, 2025

Generative AI is no longer a futuristic concept for law firms. It is here, it is powerful, and it is reshaping the business of law. Yet, despite the urgency, many firms remain caught in a cycle of experimentation — running pilot after pilot with different tools but failing to move beyond testing. The result: wasted resources, skeptical attorneys, and little measurable return on investment.

The Pitfalls of “Pilot Purgatory”


The most common mistake we see is a tool-first approach. Firms acquire licenses, set up pilots, and hope to discover use cases along the way. Without clarity about outcomes or integration into actual workflows, these efforts inevitably stall. Lawyers tire of testing tools that don’t improve their day-to-day work, and leadership loses patience with investments that don’t pay off.

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