Knowing Isn't Understanding: Re-grounding Generative Proactivity with Epistemic and Behavioral Insight

Proactive LLM agents can turn idle compute into useful support before users ask. Yet even correct work can misread user context, impose review costs, or undermine trust. This work proposes foundations for designing, realizing, and evaluating proactive LLM agents around three joint principles (3T): Task Capability, anticipating relevant needs and correctly performing useful work; Temporal Allocation, allocating compute according to resource availability and when results are needed; and Trust, sustaining users' confidence and appropriate reliance on the agent. We connect these objectives to a design space organized around five dimensions: task scope, anticipation horizon, activation trigger, processing timing, and intervention depth, and specify the situation and system modeling needed to support its choices, including user and environment representations, backbone LLMs, and agent harnesses. Lastly, we propose PROACTIVITY-GYM, a simulation-based evaluation testbed including multi-day scenarios, stateful environments, and persona-conditioned simulated users that can evaluate the consequences of proactive assistance across interactions. Evaluations across 23 model-harness configurations uncover substantial performance gaps across 3T and reveal that LLM judges often conflate task capability and trust. A human study with 30 participants demonstrates the importance of the joint 3T optimization: participants show sharp trust declines after intervention misalignment despite correct outcomes, and prefer sleep-time assistance, even when imperfect, to preserve ongoing focus. Together, these findings support designing and evaluating proactive agents through the joint consideration of useful work, compute allocation, and evolving user trust.

An agent that uses tools typically responds to what the user explicitly asks, yet completing the task may require information the user never requested. Work on proactive agents mainly studies whether and when an agent should act on its own, not what information it should pursue. We study a distinct axis of proactivity: its content. Horizontal proactivity pursues unstated information that the current context already identifies, and vertical proactivity pursues needs that only earlier evidence reveals. A need graph, recovered from a benchmark's own decomposition, records which needs depend on which, so both forms, and whether the agent stops at the right time, can be scored from a transcript without a model judge. To learn this behavior, we propose Q&D (questioner and drafter), which trains a questioner to prefer the question whose continuation retrieves more of the required evidence, with no reward model or judge. On held-out splits of three multi-hop question-answering benchmarks, at equal retrieval spend, the trained questioner improves both forms of proactivity over the same model, prompted, and outperforms a prompted model $15\times$ larger in the same role on two of the three, and the gain persists after controlling for question volume and length. Without further training, we place the questioner in an interactive customer-service agent with a simulated customer, where it completes more tasks while asking fewer questions, and in retail it outperforms the $15\times$ larger model with fewer follow-up turns from the customer. These results show that proactivity depends not only on whether an agent acts without being asked, but also on what it chooses to pursue and when it stops.

Large language model agents can plan, invoke tools, and modify external states, yet most systems still take an explicit user instruction as a fixed starting point. Proactive service moves the decision upstream: an agent must infer service opportunities from incomplete environmental and user signals, choose among remaining silent, asking, assisting, and acting, and account for interruption, misunderstanding, overreach, and privacy costs. This survey gives an operational definition centered on initiative and formulates the problem as a partially observable sequential decision process constrained by authorization and risk. The formulation represents timing, content, and delivery within one structured action, while making explicit the option value of waiting, the decision value of questions, and feedback-induced state changes. On this basis, we organize existing methods along one decision pipeline (state and need estimation, intervention gating, action construction, and feedback adaptation) and describe prescribed, predictive, model based, and return optimizing mechanisms as nonexclusive policy-construction components. We further normalize decision units and three-axis evidence descriptors across streaming dialogue, screen, video, software-engineering, and human-agent collaboration resources, and formalize metrics for triggering, timing, calibration, user burden, safety, and policy value. The synthesis shows why offline classification performance alone does not predict deployment benefit and why long-term memory is not a defining condition of proactivity. Reliable proactive service instead requires calibrated incremental intervention value, verifiable authorization, recoverable execution, and counterfactual evidence.