From early in childhood, humans exhibit sophisticated intuitions about how to share knowledge efficiently in simple controlled studies. Yet, untrained adults often fail to teach effectively in real-world situations. Here, we explored what causes adults to struggle in informal pedagogical exchanges. In Experiment 1, we first showed evidence of this effect, finding that adult participants failed to communicate their knowledge to naïve learners in a simple teaching task, despite reporting high confidence that they taught effectively. Using a computational model of rational teaching, we found that adults assigned to our teaching condition provided highly informative examples but failed to teach effectively because their examples were tailored to learners who were only considering a small set of possible explanations. In Experiment 2, we then found experimental evidence for this possibility, showing that knowledgeable participants systematically misunderstand the beliefs of naïve participants. Specifically, knowledgeable participants assumed naïve agents would primarily consider hypotheses close to the correct one. Finally, in Experiment 3, we aligned learners' beliefs to knowledgeable agents' expectations and showed learners the same examples selected by participants assigned to teach in Experiment 1. We found that these same examples were significantly more informative once learners' hypothesis spaces were constrained to match teachers' expectations. Our findings show that, in informal settings, adult pedagogical failures result from an inaccurate representation of what naïve learners believe is plausible and not an inability to select informative data in a rational way.