# Ask Before You Optimize: Dynamic Pre-Formulation Clarification for Interactive Optimization

arXiv: https://arxiv.org/abs/2609.05258 · HTML: https://mlsanity.com/paper/2609.05258/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Builds on 26 of its 29 references that are in the map.
- First posted on arXiv 4 Sep 2026.

## Builds on (most cited first, 26 of 26)

- [Language Models (Mostly) Know What They Know](https://mlsanity.com/paper/2207.05221/) (2022)
- [τ-bench: A Benchmark for Tool-Agent-User Interaction in Real-World Domains](https://mlsanity.com/paper/2406.12045/) (2024)
- [AmbigQA: Answering Ambiguous Open-domain Questions](https://mlsanity.com/paper/2004.10645/) (2020)
- [AbstentionBench: Reasoning LLMs Fail on Unanswerable Questions](https://mlsanity.com/paper/2506.09038/) (2025)
- [Asking Clarifying Questions in Open-Domain Information-Seeking Conversations](https://mlsanity.com/paper/1907.06554/) (2019)
- [NL4Opt Competition: Formulating Optimization Problems Based on Their Natural Language Descriptions](https://mlsanity.com/paper/2303.08233/) (2023)
- [ORLM: A Customizable Framework in Training Large Models for Automated Optimization Modeling](https://mlsanity.com/paper/2405.17743/) (2024)
- [OptiMUS: Scalable Optimization Modeling with (MI)LP Solvers and Large Language Models](https://mlsanity.com/paper/2402.10172/) (2024)
- [STaR-GATE: Teaching Language Models to Ask Clarifying Questions](https://mlsanity.com/paper/2403.19154/) (2024)
- [LLMOPT: Learning to Define and Solve General Optimization Problems from Scratch](https://mlsanity.com/paper/2410.13213/) (2024)
- [Clarify When Necessary: Resolving Ambiguity Through Interaction with LMs](https://mlsanity.com/paper/2311.09469/) (2023)
- [Eliciting Human Preferences with Language Models](https://mlsanity.com/paper/2310.11589/) (2023)
- [Modeling Future Conversation Turns to Teach LLMs to Ask Clarifying Questions](https://mlsanity.com/paper/2410.13788/) (2024)
- [Interpretation of Natural Language Rules in Conversational Machine Reading](https://mlsanity.com/paper/1809.01494/) (2018)
- [CLAM: Selective Clarification for Ambiguous Questions with Generative Language Models](https://mlsanity.com/paper/2212.07769/) (2022)
- [ConvAI3: Generating Clarifying Questions for Open-Domain Dialogue Systems (ClariQ)](https://mlsanity.com/paper/2009.11352/) (2020)
- [Structured Uncertainty guided Clarification for LLM Agents](https://mlsanity.com/paper/2511.08798/) (2025)
- [Asking Clarification Questions to Handle Ambiguity in Open-Domain QA](https://mlsanity.com/paper/2305.13808/) (2023)
- [StepORLM: A Self-Evolving Framework With Generative Process Supervision For Operations Research Language Models](https://mlsanity.com/paper/2509.22558/) (2025)
- [When and What to Ask: AskBench and Rubric-Guided RLVR for LLM Clarification](https://mlsanity.com/paper/2602.11199/) (2026)
- [Large-Scale Optimization Model Auto-Formulation: Harnessing LLM Flexibility via Structured Workflow](https://mlsanity.com/paper/2601.09635/) (2026)
- [TO-GATE: Clarifying Questions and Summarizing Responses with Trajectory Optimization for Eliciting Human Preference](https://mlsanity.com/paper/2506.02827/) (2025)
- [Let's Have a Conversation: Designing and Evaluating LLM Agents for Interactive Optimization](https://mlsanity.com/paper/2604.02666/) (2026)
- [CLARITY: A Framework and Benchmark for Conversational Language Ambiguity and Unanswerability in Interactive NL2SQL Systems](https://mlsanity.com/paper/2604.22313/) (2026)
- [ORPilot: A Production-Oriented Agentic LLM-for-OR Tool for Optimization Modeling](https://mlsanity.com/paper/2605.02728/) (2026)
- [OR-Space: A Full-Lifecycle Workspace Benchmark for Industrial Optimization Agents](https://mlsanity.com/paper/2605.28158/) (2026)

## Abstract (arXiv)

Large language models (LLMs) are increasingly used to formulate optimization models from natural-language problem descriptions, yet realistic operations research (OR) requests are often incomplete: missing objectives, constraints, or business rules can change the resulting mathematical program. Existing evaluations largely assume a complete specification and therefore overlook whether an agent knows when clarification is needed before modeling. We introduce OR-Clarify, a benchmark for pre-formulation clarification. Each task presents a partial public problem description, withholds structured hidden slots, and evaluates agents through bounded interaction with a simulated user. The benchmark supports both openended and choice-based clarification, and measures slot recovery, stopping behavior, silent assumptions, and interaction cost. We further propose Interactive Optimization (InterOPT), a two-stage framework that identifies unresolved formulation-critical gaps and uses them to guide whether to ask the next question or to stop. In our choice-based experiments, InterOPT substantially outperforms all baselines in exact slot recovery; in the open-ended setting, it remains competitive with strong prior methods. Together, OR-Clarify and InterOPT reframe OR assistance as a selective completeness decision: clarify when needed, stop when ready, and quantify what remains missing.