The Future of Legal

If you think law is a matter of binary right and wrong answers, you haven’t spent enough time with great lawyers. Law, as I came to see in my two weeks immersed with Crosby, is not an airless sect of transcendent values. It is an arena of taste and judgment.

As an outsider to the legal world, shadowing at Crosby meant learning an entirely new vocabulary. I perched in a corner of the company’s largest conference room, packed and uncommonly quiet. The “time trials” were about to begin: Crosby’s internal contests where lawyers race to redline a contract against the clock.

Two lawyers sat facing each other, close as chess players over a board, and started redlining. Looking over one lawyer’s shoulder, I watched him accept the AI’s redlines with a tap, then slow over a single clause. He deleted an “or” and typed “and.” It looked like eye-watering work.