Microsoft Clippy (1997)
Microsoft shipped Clippy, an animated paperclip assistant in Office 97. It popped up unsolicited to offer help, and users found it intrusive and annoying.
Clippy was widely mocked and Microsoft eventually removed it from Office.
Clippy became a cautionary tale about AI assistants that insert themselves into workflows without being asked.
Shows the failure mode for AI assistants: if they're intrusive or unhelpful, users reject them. Plane's agents are designed to be assigned work, not to pop up unsolicited.
