should agents ask for user context up front or learn it slowly?

Reddit r/AI_Agents News

Summary

A discussion on how AI agents should handle user context: upfront disclosure or gradual learning, with various existing approaches like project memory and chat summaries found lacking.

hey, im trying to understand what people are actually doing with AI agent user context. when an agent starts with zero context, it asks obvious questions and feels kind of dumb. but if it learns slowly from every run, the first few sessions are still rough. i tried project memory, but that only helps inside one workspace. tried chat summaries, but they miss preferences. tried a small user profile, but then you have to decide what belongs there. is the right pattern a user data API for agents, or should agents stay mostly stateless until the user tells them more? what are you doing for cold start with agents?
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