There a recent(ish: May 2025) paper about how drip-feeding information is worse than restarting with a revised prompt once you realize details are missing.[0] [0] https://arxiv.org/abs/2505.06120
LLMs Get Lost In Multi-Turn Conversation
Philippe Laban, Hiroaki Hayashi, Yingbo Zhou, Jennifer Neville
2025 · arXiv
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From the abstract
Large Language Models (LLMs) are conversational interfaces. As such, LLMs have the potential to assist their users not only when they can fully specify the task at hand, but also to help them define, explore, and refine what they need through multi-turn conversational exchange. Although analysis of LLM conversation logs has confirmed that underspecification occurs frequently in user instructions, LLM evaluation has predominantly focused on the single-turn, fully-specified instruction setting. In this work, we perform large-scale simulation experiments to compare LLM performance in single- and multi-turn settings. Our experiments confirm that all the top open- and closed-weight LLMs we test exhibit significantly lower performance in multi-turn conversations than single-turn, with an average drop of 39% across six generation tasks. Analysis of 200,000+ simulated conversations decomposes the performance degradation into two components: a minor loss in aptitude and a significant increase in unreliability. We find that LLMs often make assumptions in early turns and prematurely attempt to generate final solutions, on which they overly rely. In simpler terms, we discover that *when LLMs take a wrong turn in a conversation, they get lost and do not recover*.
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Looking at this thread, excited to see the community articulating what many of us have been experiencing. The shift from "prompt engineering" to "context engineering" really captures what's happening. The technical stuff (RAG, vector databases) is getting commoditized. But there's this foundational knowledge organization layer that's becoming critical. Most companies have context scattered across wikis, Slack, Google Docs. You can build sophisticated retrieval systems, but if you're feeding them fragmented information, you're missing huge optimization opportunities. There's research backing this - Microsoft/Salesforce found 39% accuracy drop in multi-turn conversations - so for the agent interaction's it's even more cirtical to give 'just enough' context (https://arxiv.org/pdf/2505.06120). When (business) context is properly structured upfront, you minimize those patterns.
That's why in practice you need more than this simple loop! Pretty much WIP, but I am experimenting with simple sequence-based workflows that are designed to frequently reset the conversation [2] This goes well with Microsoft paper "LLMs Get Lost In Multi-Turn Conversation " that was published Friday [1]. - [1]: https://arxiv.org/abs/2505.06120 - [2]: https://github.com/hbbio/nanoagent/blob/main/src/workflow.ts
Keep following the thread.
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