Clarify User Expertise: Towards Proactive Conversational Agents Tailoring Responses to User Proficiency

Large language models (LLMs) are increasingly used by end users, yet existing personalization methods relying on static profiles or text-only signals fail to capture query-specific expertise variation. We present ExPerT, a query-wise personalization framework that adapts LLM responses to users' query domain expertise by combining semantic and behavioral cues. ExPerT consists of two key components: (i) a semantic-behavioral expertise inference module that jointly interprets query text and keystroke dynamics via in-context LLM prompting, and (ii) an expertise-conditioned response generation that adapts the level of detail, terminology, and conceptual complexity. Our user study with 40 participants and 1270 queries demonstrated that ExPerT reduced expertise inference error by 65.7% compared to the strongest baseline (MAE = 0.398 vs. 1.162) and improved response satisfaction by 17.52% (from 3.71 to 4.36) on a 5-point Likert scale.

Tool-using LLM agents must decide not only whether additional information is needed, but also which source can resolve the uncertainty. Existing proactive approaches often specialize in either user clarification or environment verification, without explicitly determining the appropriate information source for each decision. We formulate this problem as uncertainty routing among ACT, CLARIFY, and VERIFY, and propose PROUR, a proactive uncertainty routing framework. PROUR decomposes action uncertainty into disagreement across plausible user-goal interpretations, which signals user-side ambiguity, and the entropy remaining within each interpretation, which signals missing world-side evidence. To acquire information from the routed source, a query generator is trained with a mode-conditioned information-gain reward, targeting user-goal identification under CLARIFY and next-action identification under VERIFY. On $τ$-bench, PROUR achieves 28.17% average success rate across retail and airline, outperforming the strongest prior method by 4.57% while using 2.17 fewer interaction steps. The learned policy further generalizes to stronger task agents and transactional domains of $τ^3$-bench without retraining, demonstrating the benefit of source-aligned uncertainty resolution for proactive agents.

Proactive agents are expected to anticipate user needs and provide autonomous assistance by perceiving environmental context without explicit instructions. A fundamental capability of such agents is to identify and track users' upcoming events, enabling continuous and event-specific assistance. For example, by recording the time and location of a planned hike, an agent can deliver weather reminders in advance or provide navigation support before departure. However, existing works on proactive agents largely overlook event-centric assistance, and the open-ended nature of proactive assistance poses challenges for reliable evaluation. To bridge these gaps, we introduce ProEvent, the first event-centric benchmark designed to assess an agent's ability to proactively maintain a user's timetable based on ongoing instant messaging chats. ProEvent provides synthesized yet realistic chats that consider the dynamic interaction among users, concurrent chat threads, and noise in the real world, and evaluates proactive agents on response timing, single-step response correctness, and multi-step response correctness. Experiments on eight LLMs and pipelines reveal that current agents frequently overact and struggle with event cancellation. Notably, even GPT-5.1 only reacts correctly in 26.7% of scenarios. Further qualitative analysis reveals fundamental limitations of current LLMs as proactive agents, particularly in detecting implicit events and reasoning from the user's first-person perspective.