Ask Optimal Questions: Aligning Large Language Models with Retriever’s Preference in Conversation
Chanwoong Yoon, Gangwoo Kim, Byeongguk Jeon, Sungdong Kim, Yohan Jo, Jaewoo Kang
Abstract
Conversational search, unlike single-turn retrieval tasks, requires understanding the current question within a dialogue context. The common approach of rewrite-then-retrieve aims to decontextualize questions to be self-sufficient for off-the-shelf retrievers, but most existing methods produce sub-optimal query rewrites due to the limited ability to incorporate signals from the retrieval results. To overcome this limitation, we present a novel framework RetPO (Retriever’s Preference Optimization), which is designed to optimize a language model (LM) for reformulating search queries in line with the preferences of the target retrieval systems. The process begins by prompting a large LM to produce various potential rewrites and then collects retrieval performance for these rewrites as the retrievers’ preferences. Through the process, we construct a large-scale dataset called RF collection, containing Retrievers’ Feedback on over 410K query rewrites across 12K conversations. Furthermore, we fine-tune a smaller LM using this dataset to align it with the retrievers’ preferences as feedback. The resulting model demonstrates superiority on two benchmarks, surpassing the previous state-of-the-art performance of rewrite-then-retrieve approaches, including GPT-3.5.- Anthology ID:
- 2025.findings-naacl.328
- Volume:
- Findings of the Association for Computational Linguistics: NAACL 2025
- Month:
- April
- Year:
- 2025
- Address:
- Albuquerque, New Mexico
- Editors:
- Luis Chiruzzo, Alan Ritter, Lu Wang
- Venue:
- Findings
- SIG:
- Publisher:
- Association for Computational Linguistics
- Note:
- Pages:
- 5899–5921
- Language:
- URL:
- https://preview.aclanthology.org/fix-sig-urls/2025.findings-naacl.328/
- DOI:
- Cite (ACL):
- Chanwoong Yoon, Gangwoo Kim, Byeongguk Jeon, Sungdong Kim, Yohan Jo, and Jaewoo Kang. 2025. Ask Optimal Questions: Aligning Large Language Models with Retriever’s Preference in Conversation. In Findings of the Association for Computational Linguistics: NAACL 2025, pages 5899–5921, Albuquerque, New Mexico. Association for Computational Linguistics.
- Cite (Informal):
- Ask Optimal Questions: Aligning Large Language Models with Retriever’s Preference in Conversation (Yoon et al., Findings 2025)
- PDF:
- https://preview.aclanthology.org/fix-sig-urls/2025.findings-naacl.328.pdf