Which Questions Improve Learning the Most? Utility Estimation of Questions with LM-based Simulations

Asking good questions is critical for comprehension and learning, yet evaluating and generating such questions remains a challenging problem. Prior work on inquisitive questions focuses on learner-generated, curiosity-driven queries and evaluates them using indirect metrics, such as salience or information gain, that do not directly capture a question's impact on actual learning outcomes. We introduce QUEST (Question Utility Estimation with Simulated Tests), a framework that uses language models to simulate learners and directly quantify the utility of a question - its contribution to exam performance. QUEST simulates a learner who asks questions and receives answers while studying a textbook chapter, then uses them to take an end-of-chapter exam. Through this simulation, the utility of each question is estimated by its direct effect on exam performance, rather than inferred indirectly based on the underlying content. To support this evaluation, we curate TEXTBOOK-EXAM, a benchmark that aligns textbook sections with end-of-section exam questions across five academic disciplines. Using QUEST, we filter for high-utility questions and fine-tune question generators via rejection sampling. Experiments show that questions generated by QUEST-trained models improve simulated test scores by over 20% compared to strong baselines that are fine-tuned using indirect metrics or leverage prompting methods. Furthermore, utility is only weakly correlated with salience and similarity to exam questions, suggesting that it captures unique signal that benefits downstream performance. QUEST offers a new outcome-driven paradigm for question evaluation and generation - one that moves beyond question-answer content toward measurable improvements in learning outcomes.