How to Get Your LLM to Generate Challenging Problems for Evaluation
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Abstract (arXiv)
The pace of evolution of Large Language Models (LLMs) necessitates new approaches for rigorous and comprehensive evaluation. Traditional human annotation is increasingly impracticable due to the complexities and costs involved in generating high-quality, challenging problems. In this work, we introduce CHASE, a unified framework to synthetically generate challenging problems using LLMs without human involvement. For a given task, our approach builds a hard problem in a bottom-up manner from simpler components. Moreover, our framework decomposes the generation process into independently verifiable sub-tasks, thereby ensuring a high level of quality and correctness. We implement CHASE to create evaluation benchmarks across three diverse domains: (1) document-based question answering, (2) repository-level code completion, and (3) math reasoning. The performance of state-of-the-art LLMs on these synthetic benchmarks lies in the range of 40-60% accuracy, thereby demonstrating the effectiveness of our framework at generating challenging problems. We publicly release our benchmarks and code.
Key facts. Cited by 11 papers in the map (data through 14 Oct 2026). First posted on arXiv 20 Feb 2025.
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Citing papers per year: 2025: 5; 2026: 6.
11 papers.
- 2025DeepSeek-R1 Thoughtology: Let's think about LLM Reasoningcited by 92
- 2025AgentFrontier: Expanding the Capability Frontier of LLM Agents with ZPD-Guided Data Synthesiscited by 14
- 2025Silencer: From Discovery to Mitigation of Self-Bias in LLM-as-Benchmark-Generatorcited by 5
- 2025Executable Functional Abstractions: Inferring Generative Programs for Advanced Math Problemscited by 4
- 2025Automating Benchmark Designcited by 3
- 2026CoEval: Ranking Language Models for Custom Tasks Without Labeled Data or Trustworthy Benchmarkscited by 2
- 2026STELLAR-E: a Synthetic, Tailored, End-to-end LLM Application Rigorous Evaluatorcited by 0
- 2026Step-by-Step Optimization-like Reasoning in LLMs over Expanding Search Spacescited by 0
- 2026VeriGeo: Controllable Geometry Question Generation with Numerical and Analytical Verificationcited by 0
- 2026Ask-E: An Environment for Calibrated Question Generationcited by 0
- 2026You Really Didn't Get That? Benchmarking Social Pragmatic Inference for Indirect and Playful Chinese Online Commentscited by 0
- 2026You Really Didn't Get That? Benchmarking Social Pragmatic Inference for Indirect and Playful Chinese Online Comments3 Sep 2026
- 2026Ask-E: An Environment for Calibrated Question Generation7 Aug 2026
- 2026VeriGeo: Controllable Geometry Question Generation with Numerical and Analytical Verification12 Jun 2026
- 2026Step-by-Step Optimization-like Reasoning in LLMs over Expanding Search Spaces3 Jun 2026
- 2026CoEval: Ranking Language Models for Custom Tasks Without Labeled Data or Trustworthy Benchmarks2 Jun 2026
- 2026STELLAR-E: a Synthetic, Tailored, End-to-end LLM Application Rigorous Evaluator27 Apr 2026
- 2025Automating Benchmark Design28 Oct 2025
- 2025AgentFrontier: Expanding the Capability Frontier of LLM Agents with ZPD-Guided Data Synthesis28 Oct 2025
- 2025Silencer: From Discovery to Mitigation of Self-Bias in LLM-as-Benchmark-Generator27 May 2025
- 2025Executable Functional Abstractions: Inferring Generative Programs for Advanced Math Problems14 Apr 2025
- 2025DeepSeek-R1 Thoughtology: Let's think about LLM Reasoning2 Apr 2025
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