His inbox gets so much mail that about half of what matters was being missed and a quarter sat in spam. His AI watches the box, sorts what is important, and messages him in a separate chat when something he cares about lands; it took a while to tune the prompt before it matched his judgment.
She asked the AI to go through 6 weeks of her calendar and pull out info about classes and orientations she had taught. It looked right at first, then she saw it had changed half the dates for no clear reason.
This one went wrong. See what happened before you try it.
After his motorcycle was stolen, his insurer offered nearly half the market value. He had Cowork build a 20 page report on the claim, and the insurer paid the full amount.
The AI sent a notification that it had spotted an email from TripIt, the vacation-planning app Ulanoff uses, about a password change he had forgotten making. The agent wanted to make sure he'd seen the email verifying it was him.
His agent reads his email, including PDF attachments, finds the dates and appointments inside, and adds them to his calendar with a check for duplicates. With two kids at different schools sending home a stream of letters, he calls it a big time saver.
Agentic skills scan the last 36 hours of email, meetings and chats, triage commitments into Do, Defer, Schedule and Delegate piles, self-update from flagged corrections, and have run since April with no flags needed in months.
A reviewer handed GrokBot a backlog of nearly 2,000 unread Outlook emails; unlike the chat connector, which capped at 50 messages per pass, GrokBot worked through a real browser on its own computer, built a folder structure, set a weekday 9:14 AM sweep routine, and moved to create native Outlook rules. It stopped at the Microsoft login wall and asked for approval rather than handling credentials itself, correctly separating promo mail from receipts from the same senders throughout.
This only partly worked. Worth knowing before you try it.
UFC fighter Justin Gaethje (verified, 3.7M followers) introduced his AI 'Highlight' for his training, travel, and business schedule. A notification reminded him of a Phoenix flight; he asked for tee times and the app showed options (Legacy, Aquila, Raven, Encanto) — he booked Raven Golf Club at 1:30 PM.
Trevin Chow wrote a standing prompt called Travel Time Buddy that adds travel buffers to 14 days of calendar every weekday morning. The agent keeps his schedule padded against transit time.
The author describes using AI to resolve a six-month-old travel medical insurance claim with Cigna. The AI called the insurer, was transparent about being an AI, conducted the call politely (impressing the representative), and — because final consent was required — called the author's phone and connected the parties so he could approve verbally.