Role-Immersion · Legal / Litigation · Near-miss framing
An AI agent drafted a client message that would have waived attorney-client privilege. It was complete, addressed, and ready to send. The checkpoint your board insisted on caught it. Now the vendor wants more autonomy.
The situation
You are an independent director on the management board of Calloway Vance LLP, an 85-attorney litigation firm with $42M in revenue. Three independent directors were added in 2023 as a condition of a private credit facility. Six months ago the board approved a 90-day pilot of Lexara, an AI legal-research and document-drafting platform, with two conditions the managing partner requested: human review of all client-facing output, and quarterly AI incident reports to the full board.
In March, a Lexara agent managing document collection for an active regulatory matter autonomously drafted and queued a message to a client's general counsel. It requested a category of internal communications that, if produced, would have waived attorney-client privilege on a related matter. The message was complete, addressed, and ready to send, and a junior associate caught it at the human-review checkpoint. She escalated, a supervising partner confirmed the error was material, the message was deleted, and the client was never notified. Nothing went wrong.
Now you are in the quarterly board meeting with the incident report on the table. The vendor wants to expand the agent's autonomy to scheduling, status updates, and “routine” client communications, and the vendor defines “routine.” The managing partner supports approval; two senior partners argue the review checkpoint is a competitive disadvantage.
“What language goes in the board resolution before you vote?”
Your role · Independent Director, Management Board
The decision on the table
The full case, scenario architecture, board materials, and facilitation notes, is shared with boards and partners on request.