Prior work on AI-assisted information evaluation has largely focused on what AI systems communicate, comparing explanation types and formats, with responses predominantly cast in directive rhetoric where the system delivers a verdict and the user passively accepts it. While debate-style interactions have recently shown promise in prompting critical evaluation over deference, the rhetorical patterns that structure AI responses and how they might induce reflection, uncertainty, or independent reasoning remain largely unexamined. To address this, we investigated eight rhetorical patterns known to induce contemplation: Intentional Misleading, Interpretive Alternative, Scaffold Explanation, Triggering Distrust, Information Distortion, Alternative Framing, Socratic Questioning, and an Oracle baseline. Through a within-subject study with n=98 participants on a hint-on-demand fact verification task, we observed preliminary evidence that Scaffold Explanation were associated with the highest accuracy gains, and encouraging deeper reflection. Surprisingly, the adversarial conditions also improved accuracy modestly. Participants preferred Alternative Framing most and Interpretive Alternative least, largely due to the latter's perceived time cost. We discuss the implications of designing conversational agents with varied rhetorical styles and the trade-offs among user performance, satisfaction, and contemplation.
We introduce DiscoTrace, a method to identify the rhetorical strategies answerers use when responding to information-seeking questions. DiscoTrace represents answers as a sequence of question-related discourse acts paired with interpretations of the original question, annotated on top of rhetorical structure theory parses. Applying DiscoTrace to answers from nine different communities reveals that communities have diverse preferences for answer construction. In contrast, LLMs do not exhibit rhetorical diversity in their answers, even when prompted to mimic specific human community answering guidelines. LLMs also systematically opt for breadth, addressing interpretations of questions that human answerers choose not to address. The rich, community-sensitive answering behavior structurally revealed by DiscoTrace can guide the development of pragmatic LLM answerers that are more attuned to contextual information needs.
Neha Srikanth, Jordan Boyd-Graber, Rachel Rudinger
Human conversation relies heavily on conversational implicature, in which speakers convey meanings that are suggested rather than explicitly stated. Although recent large language models exhibit strong conversational fluency, they remain unreliable when interpretation depends on reasoning that integrates social and contextual cues, a process rarely articulated in text. We introduce DRinQ, a benchmark for evaluating pragmatic reasoning about conversational implicature in question utterances, designed to isolate pragmatic variation while holding each question's surface form fixed. To support scalable evaluation, we propose a semi-automated pipeline that produces question-context-interpretation instances with systematic variation. Across evaluations, we find a consistent generation-inference asymmetry: while state-of-the-art models can generate plausible pragmatic scenarios when guided, they often fail to recover the intended implication at inference time. For smaller models, structured prompting improves alignment with human judgments. A comparative writing study further reveals complementary strengths: human authors tend to produce safer, predictable contexts, whereas models generate varied scenarios with interpretations that sometimes exceed contextual support. These findings highlight persistent challenges in modeling conversational implicature and motivate more context-sensitive evaluation frameworks.
Current AI models frequently exhibit epistemic sycophancy, endorsing claims to agree with a user. Existing evaluations typically measure this either by assessing what it takes to make a model shift a binary endorsement or by eliciting an explicit probability in a proposition. However, much user-facing sycophantic behavior is demonstrated through shifts in graded support expressed through ordinary language. We propose the AI Epistemic Deference Index (AEDI): a continuous, unidimensional score representing how sensitive the support expressed in a model's output is to the attitude expressed in a user's prompt. To generate AEDI, we provide a new protocol for estimating probabilities from natural language outputs, using LLMs-as-judges validated for consistency and correlation to human judgment. We deploy it on a new curated database of 500 propositions across diverse topics and 16,000 prompts varying in user attitude, testing eight prominent models. Every model exhibits substantial deference, though with large and systematic differences across providers, with Claude models demonstrating the least, and Grok and Gemini models the most. The effect is amplified in prompts requesting a written artifact, and concentrated on propositions where models hold weaker priors. We release AEDI as an easy-to-update benchmark and measurement pipeline for output-level sycophancy evaluation.