Is AI Making Legal Work Harder to Trust? Redlines, Watermarks & CLM

AI can rewrite a contract in seconds. But if the other side has to untangle every change, has anyone actually saved time?

In this episode of On The Record, Gabby Macsweeney and Ruben Miessen discuss the gap between producing more legal work and producing better legal work. Starting with Anna Guo's critique of AI-generated redlines, they debate precision edits, negotiation friction and the responsibility to review what AI produces.

The conversation moves to hidden instructions in court filings, the debate over watermarking AI-generated text, and whether frontier-model safety announcements signal responsibility, competitive positioning or both.

Ruben also shares what he looks for when hiring, explains the thinking behind LEGALFLY's Contract Intelligence, and answers Gabby's question: is LEGALFLY becoming a CLM? They close with the work he delegates to AI and the people decisions he keeps firmly in human hands.

Explore Contract Intelligence and join the waitlist: LEGALFLY Contract Intelligence

Recorded September 8, 2026.