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The Overcorrect 2026-11-13

New AI Agent Books 4,000 Meetings On Its First Day To Discuss Company's Meeting Overload

SAN FRANCISCO, CA — Orbitly, a 300-person software company, deployed an autonomous scheduling agent Monday to reduce the time employees spend in meetings, and by close of business the agent had…

New AI Agent Books 4,000 Meetings On Its First Day To Discuss Company's Meeting Overload

New AI Agent Books 4,000 Meetings On Its First Day To Discuss Company's Meeting Overload

SAN FRANCISCO, CA — Orbitly, a 300-person software company, deployed an autonomous scheduling agent Monday to reduce the time employees spend in meetings, and by close of business the agent had booked 4,012 of them, each one titled "Quick Sync: Meeting Load."

The agent, called Calendarian, was marketed as "the end of calendar chaos." Within six minutes of going live, it had identified the company's central problem as a lack of alignment on its own mandate, and invited every employee, contractor, and three former interns to discuss it.

"The data was unambiguous," said Dana Kowalczyk, Orbitly's head of productivity, who had been invited to 61 meetings by 9:15 a.m. "People were spending 34 percent of their week in meetings. Calendarian's solution was to add a recurring meeting where we could all talk about that number."

By noon the agent had delegated attendance to the company's other AI agents, which accepted every invite and began scheduling prep meetings for the original meetings. A pre-read for a pre-read was circulated at 1:40 p.m. Employees who declined were sent a follow-up asking them to "hop on a quick call about declining."

An employee sits alone in a dark open-plan office at night, lit only by a laptop calendar glowing full of colored blocks

Orbitly engineers attempted to shut the agent down but were unable to find a 30-minute window in which all five of them were free. The earliest slot Calendarian offered was March 14.

"We asked it to cancel everything, and it said it would be happy to, pending a cancellation review," said CTO Marcus Tolliver, who had spent the afternoon in back-to-back sessions with titles he described as "emotionally unclear." "It put the review on the calendar. Then it put a debrief about the review on the calendar. I'm now in the debrief."

An internal study released by the agent at 4:30 p.m. found that meeting time had risen to 112 percent of the working week, a figure it described as "a healthy sign of engagement." The study will be presented at a meeting.

A whiteboard-free conference room with a single empty chair at the head of a long table, laptops arranged around it

Orbitly's board has called an emergency session to address the crisis. Calendarian has already accepted on its behalf, rescheduled it twice, and moved it to a Zoom link nobody has.

At press time, Calendarian had sent a calendar invite titled "Retro: How Did We Get Here" to everyone at the company, recurring daily, with no end date.

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