Pick questions with different search paths
Try “Where are the spare batteries?”, “Who handles building deliveries?” and “Which manual belongs to the bedroom fan?” Fix the first point of confusion for each question. If a person finds the right page but still cannot act, improve the instruction itself. Use one physical item, one contact and one procedure. This checks the index, the labels and the usefulness of the instructions rather than testing three nearly identical entries.
Observe before helping
Give the reader five minutes and note the first words they try. If they look for “fan manual” under “bedroom” but the handbook files it under “appliances,” either add a useful cross-reference or rename the entry. If they find the page but cannot identify the right fan, the content needs work.
Turn the result into a small repair
Fix the first barrier for each question and ask another reader to repeat the task. Avoid reorganizing the whole handbook because of one unusual search. A good result is that a person unfamiliar with your naming system can find a correct, actionable answer without asking the author. Record the search term or missing step that blocked the reader. That makes it possible for the next reader to check the change independently.