Building an AI Coworker That Asks Questions Instead of Guessing

You tell your AI coworker: "create a task for the new feature." It creates the task. Assigns it to nobody. Sets priority to medium. Picks a random project. Nothing is technically wrong. But everything is useless. The AI didn't have context. And instead of asking, it guessed. This is the default behavior of every LLM tool system I've seen. Missing parameter? Use a default. Ambiguous input? Pick the most likely interpretation. The AI never stops and says "hey, who should I assign this to?" So I built a system that does exactly that. The Design: AskUserQuestion as a First-Class Tool The idea is simple: give the LLM a tool called ask_user_question that it can call like any other tool. Instead of creating a task, sending a message, or querying a database — it asks the human a question. Here's the tool definition the LLM sees: { name: "ask_user_question", description: "Ask the user a clarifying question with a rich interactive UI. Use when you need user input before proceeding. Supports free