# How You Ask Shapes What You Get: A Theory-Seeded Measurement of Articulation in Advice-Seeking LLM Conversations

arXiv: https://arxiv.org/abs/2608.29591 · HTML: https://mlsanity.com/paper/2608.29591/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Builds on 20 of its 47 references that are in the map.
- First posted on arXiv 30 Aug 2026.

## Builds on (most cited first, 20 of 20)

- [Judging LLM-as-a-Judge with MT-Bench and Chatbot Arena](https://mlsanity.com/paper/2306.05685/) (2023)
- [Fantastically Ordered Prompts and Where to Find Them: Overcoming Few-Shot Prompt Order Sensitivity](https://mlsanity.com/paper/2104.08786/) (2021)
- [Length-Controlled AlpacaEval: A Simple Way to Debias Automatic Evaluators](https://mlsanity.com/paper/2404.04475/) (2024)
- [Quantifying Language Models' Sensitivity to Spurious Features in Prompt Design or: How I learned to start worrying about prompt formatting](https://mlsanity.com/paper/2310.11324/) (2023)
- [WildChat: 1M ChatGPT Interaction Logs in the Wild](https://mlsanity.com/paper/2405.01470/) (2024)
- [From Crowdsourced Data to High-Quality Benchmarks: Arena-Hard and BenchBuilder Pipeline](https://mlsanity.com/paper/2406.11939/) (2024)
- [LMSYS-Chat-1M: A Large-Scale Real-World LLM Conversation Dataset](https://mlsanity.com/paper/2309.11998/) (2023)
- [AmbigQA: Answering Ambiguous Open-domain Questions](https://mlsanity.com/paper/2004.10645/) (2020)
- [Do Prompt-Based Models Really Understand the Meaning of their Prompts?](https://mlsanity.com/paper/2109.01247/) (2021)
- [State of What Art? A Call for Multi-Prompt LLM Evaluation](https://mlsanity.com/paper/2401.00595/) (2023)
- [Asking Clarifying Questions in Open-Domain Information-Seeking Conversations](https://mlsanity.com/paper/1907.06554/) (2019)
- [Learning to Ask Good Questions: Ranking Clarification Questions using Neural Expected Value of Perfect Information](https://mlsanity.com/paper/1805.04655/) (2018)
- [Eliciting Human Preferences with Language Models](https://mlsanity.com/paper/2310.11589/) (2023)
- [Clio: Privacy-Preserving Insights into Real-World AI Use](https://mlsanity.com/paper/2412.13678/) (2024)
- [QuestBench: Can LLMs ask the right question to acquire information in reasoning tasks?](https://mlsanity.com/paper/2503.22674/) (2025)
- [Grounding Gaps in Language Model Generations](https://mlsanity.com/paper/2311.09144/) (2023)
- [The Shifted and The Overlooked: A Task-oriented Investigation of User-GPT Interactions](https://mlsanity.com/paper/2310.12418/) (2023)
- [Navigating Rifts in Human-LLM Grounding: Study and Benchmark](https://mlsanity.com/paper/2503.13975/) (2025)
- [Conversational User-AI Intervention: A Study on Prompt Rewriting for Improved LLM Response Generation](https://mlsanity.com/paper/2503.16789/) (2025)
- [Native Design Bias: Studying the Impact of English Nativeness on Language Model Performance](https://mlsanity.com/paper/2406.17385/) (2024)

## Abstract (arXiv)

Users articulate the same advice-seeking request in different ways: some specify detailed constraints, others gesture at a vague need. Prior work treats this variation as noise to be averaged away; we instead treat it as a stable, measurable structure in the input distribution. We ask whether articulation (how people ask) forms latent dimensions separable from topic (what they ask about), and whether it is associated with how language models respond. We extract interpretable features from 16,447 advice-seeking prompts pooled from public chat corpora (WildChat, LMSYS, and ShareChat) and recover a small set of latent articulation factors that replicate across train/test splits and across corpora. Because this structure is largely separable from topic, the populations it defines cut across topics and stay invisible to topic- or task-based evaluation. The factors define a handful of recurring articulation styles, one of which stands out: a long-form but information-poor style, roughly one in six prompts in the largest corpus, where models return shorter, vaguer answers and do not ask for clarification even though under-specification is exactly the condition that warrants it. The contrast holds within every topic group and length quintile, and is not under-specification alone -- a second, equally under-specified style does draw clarifying questions. Two independent human annotators reproduce this contrast. We argue that benchmarks should stratify on articulation, and we offer the extracted structure as a measurement instrument for doing so.