Large language models increasingly serve as judges in AI evaluation, but current approaches rely on consensus preferences that ignore individual evaluator variation. We propose a novel simulation approach that combines categorical judgments with evaluator-specific auxiliary data—retrospective reasoning traces and interface telemetry—to enable LLM-based simulation of individual evaluators via in-context learning. We conduct a systematic empirical study of this approach using multi-facet data from 32 trained annotators across 4,200 preference judgments in a 4 × 4 × 4 factorial design. Our key findings: (1) The simulation approach achieves up to 9.9 percentage point improvements over the Base Judge; (2) Reasoning traces provide the largest gains with higher collection efforts, while interface telemetry often hurts rather than helps performance despite being cheaper to collect. (3) Simulation difficulty is systematic, predicted by an evaluator’s neutral usage (most clearly on Helpfulness) and divergence from consensus; the neutral-usage tendency—rather than simulatability itself—is the cross-task-stable property (r = 0.728). These results establish both the potential and limits of evaluator-specific auxiliary data for personalized evaluation, offering methodological insights for scaling individual aware AI assessment.

Large Language Models (LLMs) are increasingly used for generating code solutions, empowered by features like self-debugging and self-reflection. However, LLMs often struggle with complex programming problems without human guidance. This paper investigates the strategies employed by expert programmers to steer code-generating LLMs toward successful outcomes. Through a study involving experts using natural language to guide GPT-4, Gemini Ultra, and, Claude 3.5 Sonnet on highly difficult programming challenges, we frame our analysis using the “Socratic Feedback” paradigm for understanding effective steering strategies. By analyzing 30 conversational transcripts across all three models, we map observed feedback strategies to five stages of Socratic Questioning: Definition, Elenhus, Maieutic, Dialectic, and Counter-factual reasoning. We find evidence that by employing a combination of different Socratic feedback strategies across multiple turns, programmers successfully guided the models to solve 74% of the problems that the models initially failed to solve on their own.