Abstract: Large Language Models (LLMs) and Large Reasoning Models (LRMs) are typically evaluated on challenging benchmarks through dataset accuracy alone, providing no insight into the quality or faithfulness of their reasoning processes. We present WordPolo, a word-finding task where participants must discover an unknown target word using semantic similarity feedback. Players start with zero knowledge, make guesses, and receive distance scores (1 = correct, higher = further away). Success requires interpreting scores to navigate semantic space and systematically narrow the search. This design makes iterative reasoning and adaptive search strategies both directly observable and necessary for success. We evaluate recent LLMs (GPT-4.1, Llama 4, Claude 3.5 Haiku, Qwen 3), LRMs (o4-mini, Deepseek-R1), humans, and a novel heuristic on 1,500 puzzles. Beyond solve rates (which range from 4% to 62%), we introduce progression-based metrics that reveal models often make meaningful progress, insights that accuracy alone would miss. Our analysis shows how reasoning models can be hindered by overthinking and underthinking, while successful models exhibit human-like strategies. WordPolo demonstrates the need for benchmarks that test both reasoning process and outcomes, providing holistic measurements of model capabilities. Our code and dataset can be found at https://wordpolo-demo.vercel.app/.
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