JudgmentBench: Comparing Rubric and Preference Evaluation for Quality Assessment

Two methodologies dominate current practices of benchmarking: rubric-based scoring evaluates items against predefined criteria, whereas comparative judgment elicits pairwise preferences between outputs. Although both methodologies are widely used, the choice between them is rarely justified. We release JudgmentBench, a benchmark of 30 real-world legal tasks, paired with 1,539 rubric scores and 1,530 pairwise preference judgments collected from practicing attorneys--including at major U.S. law firms--with substantial experience. The annotations constitute the first publicly available dataset in a high-expertise domain in which both supervision signals are elicited from the same experts on the same items. Using LLM-generated outputs at three constructed quality levels, we provide an initial empirical comparison: comparative judgments recover the intended quality ordering substantially better than rubrics (mean Spearman's rank correlation of 0.908 vs. 0.150, estimated difference = 0.758 [0.494, 1.021]) while requiring less than half the annotation time. The patterns hold for human annotators and LLM autograders. Beyond this initial comparison, the paired structure of the dataset supports a broader research agenda on how expert judgment should be elicited, aggregated, and used as supervision in domains without verifiable ground truth.

HARDMath2: A Benchmark for Applied Mathematics Built by Students as Part of a Graduate Class

Large language models (LLMs) have shown remarkable progress in mathematical problem-solving, but evaluation has largely focused on problems that have exact analytical solutions or involve formal proofs, often overlooking approximation-based problems ubiquitous in applied science and engineering. To fill this gap, we build on prior work and present HARDMath2, a dataset of 211 original problems covering the core topics in an introductory graduate applied math class, including boundary-layer analysis, WKB methods, asymptotic solutions of nonlinear partial differential equations, and the asymptotics of oscillatory integrals. This dataset was designed and verified by the students and instructors of a core graduate applied mathematics course at Harvard. We build the dataset through a novel collaborative environment that challenges students to write and refine difficult problems consistent with the class syllabus, peer-validate solutions, test different models, and automatically check LLM-generated solutions against their own answers and numerical ground truths. Evaluation results show that leading frontier models still struggle with many of the problems in the dataset, highlighting a gap in the mathematical reasoning skills of current LLMs. Importantly, students identified strategies to create increasingly difficult problems by interacting with the models and exploiting common failure modes. This back-and-forth with the models not only resulted in a richer and more challenging benchmark but also led to qualitative improvements in the students' understanding of the course material, which is increasingly important as we enter an age where state-of-the-art language models can solve many challenging problems across a wide domain of fields.