Learning to Ask Good Questions: Ranking Clarification Questions using Neural Expected Value of Perfect Information
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Abstract (arXiv)
Inquiry is fundamental to communication, and machines cannot effectively collaborate with humans unless they can ask questions. In this work, we build a neural network model for the task of ranking clarification questions. Our model is inspired by the idea of expected value of perfect information: a good question is one whose expected answer will be useful. We study this problem using data from StackExchange, a plentiful online resource in which people routinely ask clarifying questions to posts so that they can better offer assistance to the original poster. We create a dataset of clarification questions consisting of ~77K posts paired with a clarification question (and answer) from three domains of StackExchange: askubuntu, unix and superuser. We evaluate our model on 500 samples of this dataset against expert human judgments and demonstrate significant improvements over controlled baselines.
Key facts. Cited by 110 papers in the map (data through 7 Oct 2026). First posted on arXiv 12 May 2018.
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Citing papers per year: 2021: 16; 2022: 13; 2023: 15; 2024: 27; 2025: 11; 2026: 28.
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- 2024The Art of Saying No: Contextual Noncompliance in Language Modelscited by 100
- 2024STaR-GATE: Teaching Language Models to Ask Clarifying Questionscited by 99
- 2023Clarify When Necessary: Resolving Ambiguity Through Interaction with LMscited by 93
- 2024What Evidence Do Language Models Find Convincing?cited by 74
- 2022Generating Literal and Implied Subquestions to Fact-check Complex Claimscited by 66
- 2021Building and Evaluating Open-Domain Dialogue Corpora with Clarifying Questionscited by 63
- 2024Ask-before-Plan: Proactive Language Agents for Real-World Planningcited by 59
- 2021Grounding 'Grounding' in NLPcited by 44
- 2022Automatic Generation of Socratic Subquestions for Teaching Math Word Problemscited by 42
- 2022Neural Approaches to Conversational Information Retrievalcited by 41
- 2021Putting Humans in the Natural Language Processing Loop: A Surveycited by 40
- 2021Ask what's missing and what's useful: Improving Clarification Question Generation using Global Knowledgecited by 40
38 more
- 2024Learning to Ask: When LLM Agents Meet Unclear Instructioncited by 38
- 2021Controllable Open-ended Question Generation with A New Question Type Ontologycited by 36
- 2022ClarifyDelphi: Reinforced Clarification Questions with Defeasibility Rewards for Social and Moral Situationscited by 36
- 2025Structured Uncertainty guided Clarification for LLM Agentscited by 34
- 2023Active Preference Inference using Language Models and Probabilistic Reasoningcited by 29
- 2022Evaluating Mixed-initiative Conversational Search Systems via User Simulationcited by 24
- 2023Asking Clarification Questions to Handle Ambiguity in Open-Domain QAcited by 24
- 2022Interactive Grounded Language Understanding in a Collaborative Environment: IGLU 2021cited by 23
- 2024On Overcoming Miscalibrated Conversational Priors in LLM-based Chatbotscited by 23
- 2021ISEEQ: Information Seeking Question Generation using Dynamic Meta-Information Retrieval and Knowledge Graphscited by 22
- 2024A Survey of Conversational Searchcited by 22
- 2021Open-domain clarification question generation without question examplescited by 20
- 2023Post-Abstention: Towards Reliably Re-Attempting the Abstained Instances in QAcited by 20
- 2024INTERS: Unlocking the Power of Large Language Models in Search with Instruction Tuningcited by 19
- 2024CLARINET: Augmenting Language Models to Ask Clarification Questions for Retrievalcited by 18
- 2022Python Code Generation by Asking Clarification Questionscited by 16
- 2026Calibrate-Then-Act: Cost-Aware Exploration in LLM Agentscited by 16
- 2026HiL-Bench (Human-in-Loop Benchmark): Do Agents Know When to Ask for Help?cited by 16
- 2021NeurIPS 2021 Competition IGLU: Interactive Grounded Language Understanding in a Collaborative Environmentcited by 15
- 2026Ask or Assume? Uncertainty-Aware Clarification-Seeking in Coding Agentscited by 15
- 2022IGLU 2022: Interactive Grounded Language Understanding in a Collaborative Environment at NeurIPS 2022cited by 14
- 2023Zero-shot Clarifying Question Generation for Conversational Searchcited by 14
- 2023Context Aware Query Rewriting for Text Rankers using LLMcited by 14
- 2024InfoLossQA: Characterizing and Recovering Information Loss in Text Simplificationcited by 14
- 2021A recipe for annotating grounded clarificationscited by 13
- 2021Analysing Mixed Initiatives and Search Strategies during Conversational Searchcited by 12
- 2021A Framework for Learning to Request Rich and Contextually Useful Information from Humanscited by 12
- 2022Quiz Design Task: Helping Teachers Create Quizzes with Automated Question Generationcited by 12
- 2023FOLLOWUPQG: Towards Information-Seeking Follow-up Question Generationcited by 12
- 2024Contextualized Evaluations: Judging Language Model Responses to Underspecified Queriescited by 12
- 2022Discord Questions: A Computational Approach To Diversity Analysis in News Coveragecited by 11
- 2023Instruction Clarification Requests in Multimodal Collaborative Dialogue Games: Tasks, and an Analysis of the CoDraw Datasetcited by 11
- 2021Diverse and Specific Clarification Question Generation with Keywordscited by 10
- 2021Generating Usage-related Questions for Preference Elicitation in Conversational Recommender Systemscited by 10
- 2022Collecting Interactive Multi-modal Datasets for Grounded Language Understandingcited by 10
- 2025HumanAgencyBench: Scalable Evaluation of Human Agency Support in AI Assistantscited by 10
- 2021Database Search Results Disambiguation for Task-Oriented Dialog Systemscited by 9
- 2023Towards a Benchmark for Scientific Understanding in Humans and Machinescited by 9
50 most cited of 110 All 110 (JSON)
- 2026Asking for What Was Never Requested: Horizontal and Vertical Proactivity in Agents29 Sep 2026
- 2026Prospective Interpretation Risk: Principled Communication Control Between LLMs27 Sep 2026
- 2026Clarify the User or Verify the World? Uncertainty Routing for Proactive Agents26 Sep 2026
- 2026LAVOIR: Teaching a Single-Pass Decision Encoder When and What to Ask with Amortized Value of Information25 Sep 2026
- 2026Clarification Is Not Correction: LLMs Fail to Let Go21 Sep 2026
- 2026When and How Should an Agent Clarify? CIGAsk: Teaching LLMs to Clarify via Counterfactual Information Gain21 Sep 2026
- 2026FinInteract: Benchmarking Clarification and Intent Integration in Ambiguous Financial Question Answering21 Sep 2026
- 2026How You Ask Shapes What You Get: A Theory-Seeded Measurement of Articulation in Advice-Seeking LLM Conversations30 Aug 2026
- 2026FinRiskAtlas: Decision-Aligned Evaluation of Large Language Models for Financial Risk Review26 Aug 2026
- 2026An Interactive Agent for Requirement-Driven Candidate Sourcing24 Aug 2026
- 2026KrishokChat: A Provenance-Traceable Multi-Task Bengali Agricultural Benchmark with Safety-Critical Chemical Advisory28 Jun 2026
- 2026Litmus: Zero-Label, Code-Driven Metric Specification for Evaluating AI Systems22 Jun 2026
38 more
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- 2026SOMA-SQL: Resolving Multi-Source Ambiguity in NL-to-SQL via Synthetic Log and Execution Probing9 Jun 2026
- 2026Knowing When to Ask: Self-Gated Clarification for Hierarchical Language Agents9 Jun 2026
- 2026Evidence-Based Intelligent Diagnostic and Therapeutic Visualization System with Large Language Models: Multi-Turn Interaction and Multimodal Treatment Plan Generation5 Jun 2026
- 2026Uncertainty-Aware Clarification in LLM Agents with Information Gain2 Jun 2026
- 2026What Am I Missing? Question-Answering as Hidden State Probing29 May 2026
- 2026Clarification Is Not Enough: Post-Clarification Answering Remains the Bottleneck in Multi-Turn QA24 May 2026
- 2026Ask Early, Ask Late, Ask Right: When Does Clarification Timing Matter for Long-Horizon Agents?8 May 2026
- 2026HiL-Bench (Human-in-Loop Benchmark): Do Agents Know When to Ask for Help?10 Apr 2026
- 2026PassiveQA: A Three-Action Framework for Epistemically Calibrated Question Answering via Supervised Finetuning6 Apr 2026
- 2026Ask or Assume? Uncertainty-Aware Clarification-Seeking in Coding Agents27 Mar 2026
- 2026Calibrate-Then-Act: Cost-Aware Exploration in LLM Agents18 Feb 2026
- 2026Teaching LLMs to Ask: Self-Querying Category-Theoretic Planning for Under-Specified Reasoning27 Jan 2026
- 2026Clarify or Answer: Reinforcement Learning for Agentic VQA with Context Under-specification23 Jan 2026
- 2026RAC: Retrieval-Augmented Clarification for Faithful Conversational Search16 Jan 2026
- 2026Dialogue Telemetry: Turn-Level Instrumentation for Autonomous Information Gathering14 Jan 2026
- 2025Socratic Students: Teaching Language Models to Learn by Asking Questions15 Dec 2025
- 2025PRInTS: Reward Modeling for Long-Horizon Information Seeking24 Nov 2025
- 2025Structured Uncertainty guided Clarification for LLM Agents11 Nov 2025
- 2025Shoot First, Ask Questions Later? Building Rational Agents that Explore and Act Like People23 Oct 2025
- 2025From Answers to Guidance: A Proactive Dialogue System for Legal Documents22 Oct 2025
- 2025Asking Clarifying Questions for Preference Elicitation With Large Language Models13 Oct 2025
- 2025Learning to Detect Relevant Contexts and Knowledge for Response Selection in Retrieval-based Dialogue Systems26 Sep 2025
- 2025HumanAgencyBench: Scalable Evaluation of Human Agency Support in AI Assistants10 Sep 2025
- 2025Exploring the Secondary Risks of Large Language Models14 Jun 2025
- 2025Disambiguation in Conversational Question Answering in the Era of LLMs and Agents: A Survey18 May 2025
- 2025Multi-Turn Multi-Modal Question Clarification for Enhanced Conversational Understanding17 Feb 2025
- 2024INTERACT: Enabling Interactive, Question-Driven Learning in Large Language Models16 Dec 2024
- 2024MAPLE: A Framework for Active Preference Learning Guided by Large Language Models10 Dec 2024
- 2024Learning to Ask: Conversational Product Search via Representation Learning18 Nov 2024
- 2024Contextualized Evaluations: Judging Language Model Responses to Underspecified Queries11 Nov 2024
- 2024AGENT-CQ: Automatic Generation and Evaluation of Clarifying Questions for Conversational Search with LLMs25 Oct 2024
- 2024A Survey of Conversational Search21 Oct 2024
- 2024Corpus-informed Retrieval Augmented Generation of Clarifying Questions27 Sep 2024
- 2024Broadening Access to Simulations for End-Users via Large Language Models: Challenges and Opportunities3 Sep 2024
- 2024Learning to Ask: When LLM Agents Meet Unclear Instruction31 Aug 2024
- 2024I Could've Asked That: Reformulating Unanswerable Questions24 Jul 2024
- 2024The Art of Saying No: Contextual Noncompliance in Language Models2 Jul 2024
50 newest of 110 All 110 (JSON)
- 2024Ask-before-Plan: Proactive Language Agents for Real-World Planningcited by 59
- 2024Learning to Ask: When LLM Agents Meet Unclear Instructioncited by 38
- 2025Structured Uncertainty guided Clarification for LLM Agentscited by 34
- 2026Calibrate-Then-Act: Cost-Aware Exploration in LLM Agentscited by 16
- 2026HiL-Bench (Human-in-Loop Benchmark): Do Agents Know When to Ask for Help?cited by 16
- 2026Ask or Assume? Uncertainty-Aware Clarification-Seeking in Coding Agentscited by 15
- 2024AGENT-CQ: Automatic Generation and Evaluation of Clarifying Questions for Conversational Search with LLMscited by 7
- 2025Shoot First, Ask Questions Later? Building Rational Agents that Explore and Act Like Peoplecited by 7
- 2025Disambiguation in Conversational Question Answering in the Era of LLMs and Agents: A Surveycited by 6
- 2026Uncertainty-Aware Clarification in LLM Agents with Information Gaincited by 6
- 2026Clarify or Answer: Reinforcement Learning for Agentic VQA with Context Under-specificationcited by 2
- 2026An Interactive Agent for Requirement-Driven Candidate Sourcingcited by 1
12 most cited of 18 All 18 (JSON)
- 2026Prospective Interpretation Risk: Principled Communication Control Between LLMs27 Sep 2026
- 2026Clarify the User or Verify the World? Uncertainty Routing for Proactive Agents26 Sep 2026
- 2026When and How Should an Agent Clarify? CIGAsk: Teaching LLMs to Clarify via Counterfactual Information Gain21 Sep 2026
- 2026FinInteract: Benchmarking Clarification and Intent Integration in Ambiguous Financial Question Answering21 Sep 2026
- 2026An Interactive Agent for Requirement-Driven Candidate Sourcing24 Aug 2026
- 2026Litmus: Zero-Label, Code-Driven Metric Specification for Evaluating AI Systems22 Jun 2026
- 2026Knowing When to Ask: Self-Gated Clarification for Hierarchical Language Agents9 Jun 2026
- 2026Uncertainty-Aware Clarification in LLM Agents with Information Gain2 Jun 2026
- 2026HiL-Bench (Human-in-Loop Benchmark): Do Agents Know When to Ask for Help?10 Apr 2026
- 2026Ask or Assume? Uncertainty-Aware Clarification-Seeking in Coding Agents27 Mar 2026
- 2026Calibrate-Then-Act: Cost-Aware Exploration in LLM Agents18 Feb 2026
- 2026Clarify or Answer: Reinforcement Learning for Agentic VQA with Context Under-specification23 Jan 2026
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- 2024What Evidence Do Language Models Find Convincing?cited by 74
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- 2024Corpus-informed Retrieval Augmented Generation of Clarifying Questionscited by 2
- 2026PassiveQA: A Three-Action Framework for Epistemically Calibrated Question Answering via Supervised Finetuningcited by 1
- 2026RAC: Retrieval-Augmented Clarification for Faithful Conversational Searchcited by 0
- 2026PassiveQA: A Three-Action Framework for Epistemically Calibrated Question Answering via Supervised Finetuning6 Apr 2026
- 2026RAC: Retrieval-Augmented Clarification for Faithful Conversational Search16 Jan 2026
- 2024Corpus-informed Retrieval Augmented Generation of Clarifying Questions27 Sep 2024
- 2024Dynamic Contexts for Generating Suggestion Questions in RAG Based Conversational Systems18 Mar 2024
- 2024What Evidence Do Language Models Find Convincing?19 Feb 2024
- 2023Active Preference Inference using Language Models and Probabilistic Reasoningcited by 29
- 2026Teaching LLMs to Ask: Self-Querying Category-Theoretic Planning for Under-Specified Reasoningcited by 2
- 2026What Am I Missing? Question-Answering as Hidden State Probingcited by 1
- 2026Evidence-Based Intelligent Diagnostic and Therapeutic Visualization System with Large Language Models: Multi-Turn Interaction and Multimodal Treatment Plan Generationcited by 0
- 2026Evidence-Based Intelligent Diagnostic and Therapeutic Visualization System with Large Language Models: Multi-Turn Interaction and Multimodal Treatment Plan Generation5 Jun 2026
- 2026What Am I Missing? Question-Answering as Hidden State Probing29 May 2026
- 2026Teaching LLMs to Ask: Self-Querying Category-Theoretic Planning for Under-Specified Reasoning27 Jan 2026
- 2023Active Preference Inference using Language Models and Probabilistic Reasoning19 Dec 2023
- 2025PRInTS: Reward Modeling for Long-Horizon Information Seeking24 Nov 2025
- 2025Exploring the Secondary Risks of Large Language Models14 Jun 2025
- 2024The Art of Saying No: Contextual Noncompliance in Language Modelscited by 100
- 2024STaR-GATE: Teaching Language Models to Ask Clarifying Questionscited by 99
- 2023Clarify When Necessary: Resolving Ambiguity Through Interaction with LMscited by 93
- 2022Generating Literal and Implied Subquestions to Fact-check Complex Claimscited by 66
- 2021Building and Evaluating Open-Domain Dialogue Corpora with Clarifying Questionscited by 63
- 2021Grounding 'Grounding' in NLPcited by 44
- 2022Automatic Generation of Socratic Subquestions for Teaching Math Word Problemscited by 42
- 2022Neural Approaches to Conversational Information Retrievalcited by 41
- 2021Putting Humans in the Natural Language Processing Loop: A Surveycited by 40
- 2021Ask what's missing and what's useful: Improving Clarification Question Generation using Global Knowledgecited by 40
- 2021Controllable Open-ended Question Generation with A New Question Type Ontologycited by 36
- 2022ClarifyDelphi: Reinforced Clarification Questions with Defeasibility Rewards for Social and Moral Situationscited by 36
12 most cited of 81 All 81 (JSON)
- 2026Asking for What Was Never Requested: Horizontal and Vertical Proactivity in Agents29 Sep 2026
- 2026LAVOIR: Teaching a Single-Pass Decision Encoder When and What to Ask with Amortized Value of Information25 Sep 2026
- 2026Clarification Is Not Correction: LLMs Fail to Let Go21 Sep 2026
- 2026How You Ask Shapes What You Get: A Theory-Seeded Measurement of Articulation in Advice-Seeking LLM Conversations30 Aug 2026
- 2026FinRiskAtlas: Decision-Aligned Evaluation of Large Language Models for Financial Risk Review26 Aug 2026
- 2026KrishokChat: A Provenance-Traceable Multi-Task Bengali Agricultural Benchmark with Safety-Critical Chemical Advisory28 Jun 2026
- 2026Debiasing Without Protected Attributes: Latent Concept Erasure from Textual Profiles10 Jun 2026
- 2026SOMA-SQL: Resolving Multi-Source Ambiguity in NL-to-SQL via Synthetic Log and Execution Probing9 Jun 2026
- 2026Clarification Is Not Enough: Post-Clarification Answering Remains the Bottleneck in Multi-Turn QA24 May 2026
- 2026Ask Early, Ask Late, Ask Right: When Does Clarification Timing Matter for Long-Horizon Agents?8 May 2026
- 2026Dialogue Telemetry: Turn-Level Instrumentation for Autonomous Information Gathering14 Jan 2026
- 2025Socratic Students: Teaching Language Models to Learn by Asking Questions15 Dec 2025
12 newest of 81 All 81 (JSON)