Interactions with large language models (LLMs) often yield long and detailed responses, leveraging both parametric knowledge and retrieval-augmented generation (RAG). While these responses can provide rich insights, they often include redundant or less engaging content not aligned with user interests. This issue becomes apparent when users specify particular subtopics to include or exclude – termed **coverage-conditioned (C²)** queries – as LLMs often struggle to provide tailored responses. To address this challenge, we investigate the role of query outlines, sequences of subqueries designed to guide LLMs in generating responses that meet specific user requirements. To systematically create and evaluate these outlines, we introduce **QTree**, a dataset of 10K hierarchical sets of information-seeking subqueries that define structured boundaries for outline creation and evaluation in C² scenarios. Additionally, we develop **QPlanner**, a 7B language model trained to generate customized outlines within boundaries of QTree. We evaluate the effectiveness of the generated outlines through automatic and human judgements, focusing on their impact within retrieval-augmented generation (RAG) systems. Experimental results demonstrate that QPlanner, especially when trained with alignment techniques like DPO, generates higher-quality outlines that better fulfill diverse user needs.

As language models (LMs) become capable of handling a wide range of tasks, their evaluation is becoming as challenging as their development. Most generation benchmarks currently assess LMs using abstract evaluation criteria-like helpfulness and harmlessness-which often lack the flexibility and granularity of human assessment. Additionally, these benchmarks tend to focus disproportionately on specific capabilities such as instruction following, leading to coverage bias. To overcome these limitations, we introduce the BiGGen Bench, a principled generation benchmark designed to thoroughly evaluate nine distinct capabilities of LMs across 77 diverse tasks. A key feature of the BiGGen Bench is its use of instance-specific evaluation criteria, closely mirroring the nuanced discernment of human evaluation. We apply this benchmark to assess 100 frontier LMs using five evaluator LMs. Our code, data, and evaluation results are all publicly available at https://github.com/prometheus-eval/prometheus-eval.