Robots can recover from failures by asking bystanders for help, but effective human-in-the-loop recovery requires communication that accounts for differences in people's knowledge. Prior inverse-semantics work generates requests using a single listener model, leaving differences in listener knowledge untested. We introduce Listener Differences in Human-Robot Interaction (LD-HRI), a game, dataset, and benchmark that evaluates speakers through human listener performance. Our evaluation examines request properties, large language model (LLM) speakers, and inverse-semantics request-selection algorithms under controlled differences in listener information. The corpus contains 446 human-written requests and 1{,}302 listener trials. We additionally evaluated 24 frozen LLM-written requests with 70 human listeners across 560 trials. Novice success is descriptively higher with model-written requests across all four tasks, yet both request sources leave substantial expert--novice gaps, including 16 percentage points for LLM requests. LD-HRI makes these gaps measurable, providing a foundation for designing more robust communication in human-robot and human-agent interaction.

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