Summary: A chat box looks simple but is a hard interface: users can ask anything and expect anything, yet nothing in the UI shows what the AI can actually do, and backend upgrades (new tools, skills, reasoning) are invisible. Unlike deterministic products, there’s no clear funnel. “Proactive AI” closes the gap by designing features that tell users what’s possible, inside and outside the text box, and by bringing AI answers to people where they already work, avoiding cognitive leaps that lose users.

Key ideas

Disagreements & open questions

Takeaways

agent-workspaces · llm-evals · context-engineering