In those cases, one option is to offer people opportunities to build their skill and knowledge and to practice. Another is to adjust what you are asking people to do so that it falls within their abilities. A third is to make the environment safe for experiment and play.
One detective tool is Jerry Weinberg's Rule of Three Interpretations: Before responding to any one interpretation of the clues, think of at least two other possible meanings [Weinberg]. Then, check to find out what the person actually meant.
Also helpful is Miller's Law, which says, "To understand what another person is saying, you have to assume it is true and try to imagine what it might be true of." [Elgin]. When you want to understand what someone is saying, you can apply Miller's Law by asking yourself, "In order for this statement to be true, what else would have to be true? Under what circumstances would it be true? In order for me to believe that, what else would I have to believe?" I call these questions "Presupposition Probes," because they expose presuppositions, the unstated, but implied, meanings in the statement. Presuppositions always carry information about the person's expectations or beliefs.
If you want to understand a person's point of view, you must have a relationship that supports clear, honest communication. If you suspect that your relationship leading to resistance, set your request aside temporarily and focus on improving the relationship.
Sometimes what people need most from their environment is accurate information.