Expert takes Aug 31, 2026

This week · posted August 30

Simon Willison: OpenAI explains its new product in terms of what it is for rather than what it does — so he went and asked the product itself.

Simon Willison co-created the open-source web framework Django and has spent years publicly testing AI tools and writing down what he finds, item by item. He spent a while working through ChatGPT Work, which OpenAI released on July 9, and his conclusion is blunt. The official documentation defines the product by when you should reach for it: you want a deck, an analysis, a deliverable file. He judges that close to information-free, because ordinary ChatGPT already does those things. What he assembled instead is a list of capabilities: a code execution environment with network access, a browser with no interface, a file system shared across conversations, the ability to dispatch sub-tasks, and schedulable automation. After publishing, he did something more direct still: he opened a fresh session and asked the system to list every tool it holds, sort them into categories and explain each one, as a website. It listed 223 registered tools, 6 of them his own connections (Simon Willison, 08-30). The problem he names sits one layer down — OpenAI still does not publish its system prompts or tool descriptions. In his words: "If the ChatGPT Work documentation included the exact system prompt and tool descriptions used by the agent I wouldn't have needed to write this post." Why it is worth keeping: deciding whether an agent product can enter your own workflows takes a tool list and a permissions boundary, not marketing copy about use cases. Today that list exists because a user asked for it, not because the vendor supplied it. For procurement and security review that is an action already sitting on the table: you can ask it too.