From Feedback to Checklists: Grounded Evaluation of AI-Generated Clinical Notes

AI-generated clinical notes are increasingly used in healthcare, but evaluating their quality remains a challenge due to high subjectivity and limited scalability of expert review. Existing automated metrics often fail to align with real-world physician preferences. To address this, we propose a pipeline that systematically distills real user feedback into structured checklists for note evaluation. These checklists are designed to be interpretable, grounded in human feedback, and enforceable by LLM-based evaluators. Using deidentified data from over 21,000 clinical encounters, prepared in accordance with the HIPAA safe harbor standard, from a deployed AI medical scribe system, we show that our feedback-derived checklist outperforms baseline approaches in our offline evaluations in coverage, diversity, and predictive power for human ratings. Extensive experiments confirm the checklist's robustness to quality-degrading perturbations, significant alignment with clinician preferences, and practical value as an evaluation methodology. In offline research settings, the checklist can help identify notes likely to fall below our chosen quality thresholds.

AbsenceBench: Language Models Can't Tell What's Missing

Large language models (LLMs) are increasingly capable of processing long inputs and locating specific information within them, as evidenced by their performance on the Needle in a Haystack (NIAH) test. However, while models excel at recalling surprising information, they still struggle to identify clearly omitted information. We introduce AbsenceBench to assesses LLMs' capacity to detect missing information across three domains: numerical sequences, poetry, and GitHub pull requests. AbsenceBench asks models to identify which pieces of a document were deliberately removed, given access to both the original and edited contexts. Despite the apparent straightforwardness of these tasks, our experiments reveal that even state-of-the-art models like Claude-3.7-Sonnet achieve only 69.6% F1-score with a modest average context length of 5K tokens. Our analysis suggests this poor performance stems from a fundamental limitation: Transformer attention mechanisms cannot easily attend to "gaps" in documents since these absences don't correspond to any specific keys that can be attended to. Overall, our results and analysis provide a case study of the close proximity of tasks where models are already superhuman (NIAH) and tasks where models breakdown unexpectedly (AbsenceBench).

The Curious Language Model: Strategic Test-Time Information Acquisition

Decision-makers often possess insufficient information to render a confident decision. In these cases, the decision-maker can often undertake actions to acquire the necessary information about the problem at hand, e.g., by consulting knowledgeable authorities or by conducting experiments. Importantly, different levers of information acquisition come with different costs, posing the challenge of selecting the actions that are both informative and cost-effective. In this work, we propose CuriosiTree, a heuristic-based, test-time policy for zero-shot information acquisition in large language models (LLMs). CuriosiTree employs a greedy tree search to estimate the expected information gain of each action and strategically chooses actions based on a balance of anticipated information gain and associated cost. Empirical validation in a clinical diagnosis simulation shows that CuriosiTree enables cost-effective integration of heterogenous sources of information, and outperforms baseline action selection strategies in selecting action sequences that enable accurate diagnosis.

CLEAR: A Clinically-Grounded Tabular Framework for Radiology Report Evaluation

Existing metrics often lack the granularity and interpretability to capture nuanced clinical differences between candidate and ground-truth radiology reports, resulting in suboptimal evaluation. We introduce a Clinically-grounded tabular framework with Expert-curated labels and Attribute-level comparison for Radiology report evaluation (CLEAR). CLEAR not only examines whether a report can accurately identify the presence or absence of medical conditions, but also assesses whether it can precisely describe each positively identified condition across five key attributes: first occurrence, change, severity, descriptive location, and recommendation. Compared to prior works, CLEAR's multi-dimensional, attribute-level outputs enable a more comprehensive and clinically interpretable evaluation of report quality. Additionally, to measure the clinical alignment of CLEAR, we collaborate with five board-certified radiologists to develop CLEAR-Bench, a dataset of 100 chest X-ray reports from MIMIC-CXR, annotated across 6 curated attributes and 13 CheXpert conditions. Our experiments show that CLEAR achieves high accuracy in extracting clinical attributes and provides automated metrics that are strongly aligned with clinical judgment.

Concept Incongruence: An Exploration of Time and Death in Role Playing

Consider this prompt "Draw a unicorn with two horns". Should large language models (LLMs) recognize that a unicorn has only one horn by definition and ask users for clarifications, or proceed to generate something anyway? We introduce concept incongruence to capture such phenomena where concept boundaries clash with each other, either in user prompts or in model representations, often leading to under-specified or mis-specified behaviors. In this work, we take the first step towards defining and analyzing model behavior under concept incongruence. Focusing on temporal boundaries in the Role-Play setting, we propose three behavioral metrics--abstention rate, conditional accuracy, and answer rate--to quantify model behavior under incongruence due to the role's death. We show that models fail to abstain after death and suffer from an accuracy drop compared to the Non-Role-Play setting. Through probing experiments, we identify two main causes: (i) unreliable encoding of the "death" state across different years, leading to unsatisfactory abstention behavior, and (ii) role playing causes shifts in the model's temporal representations, resulting in accuracy drops. We leverage these insights to improve consistency in the model's abstention and answer behaviors. Our findings suggest that concept incongruence leads to unexpected model behaviors and point to future directions on improving model behavior under concept incongruence.

HyPerAlign: Hypotheses-driven Personalized Alignment

Alignment algorithms are widely used to align large language models (LLMs) to human users based on preference annotations that reflect their intended real-world use cases. Typically these (often divergent) preferences are aggregated over a diverse set of users, resulting in fine-tuned models that are aligned to the ``average-user'' preference. Nevertheless, current models are used by individual users in very specific contexts and situations, emphasizing the need for user-dependent preference control. In this work we address the problem of personalizing LLM outputs to their users, aiming to generate customized responses tailored to individual users, instead of generic outputs that emulate the collective voices of diverse populations. We propose a novel interpretable and sample-efficient hypotheses-driven personalization approach (HyPerAlign) where given few-shot examples written by a particular user, we first infer hypotheses about their communication strategies, personality and writing style, then prompt LLM models with these hypotheses and user specific attributes to generate customized outputs. We conduct experiments on two different personalization tasks, authorship attribution and deliberative alignment, with datasets from diverse domains (news articles, blog posts, emails, jailbreaking benchmarks), and demonstrate the superiority of hypotheses-driven personalization approach when compared to preference-based fine-tuning methods. For deliberative alignment, the helpfulness of LLM models is improved by up to $70\%$ on average. For authorship attribution, results indicate consistently high win-rates (commonly $>90\%$) against state-of-the-art preference fine-tuning approaches for LLM personalization across diverse user profiles and LLM models. Overall, our approach represents an interpretable and sample-efficient strategy for the personalization of LLM models to individual users.

HypoBench: Towards Systematic and Principled Benchmarking for Hypothesis Generation

There is growing interest in hypothesis generation with large language models (LLMs). However, fundamental questions remain: what makes a good hypothesis, and how can we systematically evaluate methods for hypothesis generation? To address this, we introduce HypoBench, a novel benchmark designed to evaluate LLMs and hypothesis generation methods across multiple aspects, including practical utility, generalizability, and hypothesis discovery rate. HypoBench includes 7 real-world tasks and 5 synthetic tasks with 194 distinct datasets. We evaluate four state-of-the-art LLMs combined with six existing hypothesis-generation methods. Overall, our results suggest that existing methods are capable of discovering valid and novel patterns in the data. However, the results from synthetic datasets indicate that there is still significant room for improvement, as current hypothesis generation methods do not fully uncover all relevant or meaningful patterns. Specifically, in synthetic settings, as task difficulty increases, performance significantly drops, with best models and methods only recovering 38.8% of the ground-truth hypotheses. These findings highlight challenges in hypothesis generation and demonstrate that HypoBench serves as a valuable resource for improving AI systems designed to assist scientific discovery.

HypoEval: Hypothesis-Guided Evaluation for Natural Language Generation

Large language models (LLMs) have demonstrated great potential for automating the evaluation of natural language generation. Previous frameworks of LLM-as-a-judge fall short in two ways: they either use zero-shot setting without consulting any human input, which leads to low alignment, or fine-tune LLMs on labeled data, which requires a non-trivial number of samples. Moreover, previous methods often provide little reasoning behind automated evaluations. In this paper, we propose HypoEval, Hypothesis-guided Evaluation framework, which first uses a small corpus of human evaluations to generate more detailed rubrics for human judgments and then incorporates a checklist-like approach to combine LLM's assigned scores on each decomposed dimension to acquire overall scores. With only 30 human evaluations, HypoEval achieves state-of-the-art performance in alignment with both human rankings (Spearman correlation) and human scores (Pearson correlation), on average outperforming G-Eval by 11.86% and fine-tuned Llama-3.1-8B-Instruct with at least 3 times more human evaluations by 11.95%. Furthermore, we conduct systematic studies to assess the robustness of HypoEval, highlighting its effectiveness as a reliable and interpretable automated evaluation framework.

On the Effectiveness and Generalization of Race Representations for Debiasing High-Stakes Decisions

Understanding and mitigating biases is critical for the adoption of large language models (LLMs) in high-stakes decision-making. We introduce Admissions and Hiring, decision tasks with hypothetical applicant profiles where a person's race can be inferred from their name, as simplified test beds for racial bias. We show that Gemma 2B Instruct and LLaMA 3.2 3B Instruct exhibit strong biases. Gemma grants admission to 26% more White than Black applicants, and LLaMA hires 60% more Asian than White applicants. We demonstrate that these biases are resistant to prompt engineering: multiple prompting strategies all fail to promote fairness. In contrast, using distributed alignment search, we can identify "race subspaces" within model activations and intervene on them to debias model decisions. Averaging the representation across all races within the subspaces reduces Gemma's bias by 37-57%. Finally, we examine the generalizability of Gemma's race subspaces, and find limited evidence for generalization, where changing the prompt format can affect the race representation. Our work suggests mechanistic approaches may provide a promising venue for improving the fairness of LLMs, but a universal race representation remains elusive.

CaseSumm: A Large-Scale Dataset for Long-Context Summarization from U.S. Supreme Court Opinions

This paper introduces CaseSumm, a novel dataset for long-context summarization in the legal domain that addresses the need for longer and more complex datasets for summarization evaluation. We collect 25.6K U.S. Supreme Court (SCOTUS) opinions and their official summaries, known as "syllabuses." Our dataset is the largest open legal case summarization dataset, and is the first to include summaries of SCOTUS decisions dating back to 1815. We also present a comprehensive evaluation of LLM-generated summaries using both automatic metrics and expert human evaluation, revealing discrepancies between these assessment methods. Our evaluation shows Mistral 7b, a smaller open-source model, outperforms larger models on most automatic metrics and successfully generates syllabus-like summaries. In contrast, human expert annotators indicate that Mistral summaries contain hallucinations. The annotators consistently rank GPT-4 summaries as clearer and exhibiting greater sensitivity and specificity. Further, we find that LLM-based evaluations are not more correlated with human evaluations than traditional automatic metrics. Furthermore, our analysis identifies specific hallucinations in generated summaries, including precedent citation errors and misrepresentations of case facts. These findings demonstrate the limitations of current automatic evaluation methods for legal summarization and highlight the critical role of human evaluation in assessing summary quality, particularly in complex, high-stakes domains. CaseSumm is available at https://huggingface.co/datasets/ChicagoHAI/CaseSumm