When Gradients Collide: Failure Modes of Multi-Objective Prompt Optimization for LLM Judges

This work explores the role of prompt design and judge selection in LLM-as-a-Judge evaluations of free text legal question answering. We examine whether automatic task prompt optimization improves over human-centered design, whether optimization effectiveness varies by judge feedback style, and whether optimized prompts transfer across judges. We systematically address these questions on the LEXam benchmark by optimizing task prompts using the ProTeGi method with feedback from two judges (Qwen3-32B, DeepSeek-V3) across four task models, and then testing cross-judge transfer. Automatic optimization consistently outperforms the baseline, with lenient judge feedback yielding higher and more consistent gains than strict judge feedback. Prompts optimized with lenient feedback transfer better to strict judges than the reverse direction. Analysis reveals that lenient judges provide permissive feedback, yielding prompts with broader applicability, whereas strict judges produce restrictive feedback, leading to judge-specific overfitting. Our findings demonstrate algorithmically optimizing prompts on training data can outperform human-centered prompt design and that judges' dispositions during optimization shape prompt generalizability.

Large language models are widely adopted as automated evaluation judges, yet the stability of their verdicts under semantically equivalent prompt rephrasings remains largely unexamined. We conduct a systematic empirical study of prompt-induced decision instability across multiple evaluation tasks and judge architectures. To facilitate this analysis, we release JudgeSense, a benchmark comprising hand-validated prompt-paraphrase pairs spanning factuality, coherence, relevance, and preference, drawn from established NLP benchmarks and accompanied by comprehensive decision logs. The benchmark enables the measurement of judge stability across equivalent prompts, allowing researchers to assess whether stability correlates with model scale or instruction-tuning, and to identify which tasks are most sensitive to prompt wording. Our evaluation reveals that coherence remains the primary task for distinguishing judge behavior, while factuality judgments demonstrate high stability under standard conditions. Pairwise evaluation tasks consistently exhibit position bias. Crucially, we find that model scale is not a reliable proxy for consistency; notably, as an interesting result in our analysis, the largest and newest models are not the most consistent.

LLM-as-a-judge is now the default measurement instrument for open-ended generation, but on the public JudgeBench benchmark even strong instruction-tuned judges barely scrape past random on objective-correctness pairwise items. We introduce RTLC, a three-stage prompting recipe -- Research, Teach-to-Learn, Critique -- that promotes a single black-box LLM into an ensemble-of-thought judge with no fine-tuning, retrieval, or external tools. Stage 1 wraps the input in a fixed pedagogical scaffold porting the Feynman Learning Technique (study $\to$ teach $\to$ find gaps $\to$ simplify) into LLM prompting. Stage 2 draws N=10 independent candidate verdicts at temperature 0.4. Stage 3 acts as its own critic, cross-comparing the candidate set against the original question to emit one critiqued verdict at temperature 0. On JudgeBench-GPT (350 hard pairwise items), Claude 3.7 Sonnet's pairwise accuracy climbs from 64.6% (single-shot vanilla prompt) to 78.6% (RTLC critique-of-10) -- an absolute 14.0-percentage-point gain. RTLC also beats N=10 self-consistency majority voting (77.7%) and a zero-shot first candidate (74.0%). A clean three-step ablation attributes +9.4 pp to the Teach-to-Learn scaffold, +3.7 pp to N=10 marginalisation, and +0.9 pp to explicit critique. We discuss the cost-accuracy frontier (RTLC sits above self-consistency at every working point), the error-budget breakdown across the four JudgeBench categories (knowledge, reasoning, math, coding), and how RTLC composes orthogonally with post-hoc judge-score calibration, with the two interventions compounding multiplicatively in practice.