The same Cowork setup checks his father's email for work orders and schedules his father's meetings automatically. He turned off data sharing with AI for this, so the mail is not saved anywhere else.
Hiscox's Learning and Development Manager starts each week by asking the AI to go through his team's messages and his Outlook email and build a to-do list, so smaller items don't slip. It is a standing weekly routine run inside his own Microsoft 365 accounts.
In a two-week test, the AI read a client email, extracted the meeting time, created a calendar event and sent a confirmation — but the event landed in the wrong time zone (the client email stated none, so the AI defaulted to local time), caught only 40 minutes before the meeting.
This only partly worked. Worth knowing before you try it.
He pays per token for small API jobs. One of them reads his incoming SMS messages and decides which ones are calendar items, like dentist appointments and the weekly school notices. The whole setup cost him $1.50 over six months.
He helped his brother with the website of Ichtus Vlaanderen, an NGO he used to work for. Using the AI through the WordPress.com MCP connector, he fixed design problems like a messy photo section and buttons that were too big.
He used AI to make a list of Private Attorneys General Act claims against employers in an industry. The list was made in support of an organizing drive, and he says the tool is almost always helpful on tasks that involve a lot of data.
The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.
This one went wrong. See what happened before you try it.
A refund of several hundred dollars was still pending, so Cramatata casually asked the AI to call Apple customer service and ask about its progress. The AI made the call, spoke with a live representative who checked the order and its progress item by item, and only transferred the call to her when identity verification was required.