We used the stages of the question response model as a framework to discuss the challenges in administering standardized measures to older adults hospitalized with chronic illnesses. Items with complex content and those with negative stems were associated with difficulties during the comprehension stage. Present experience with the subject of the item was a barrier to retrieving past experiences. The lack of relevance of an item's content to the respondent's situation was associated with problems during the judgment stage. The numeric response format of the items was an obstacle during the response stage. Strategies to enhance the validity of the surveys included breaking up, rephrasing, and contextualizing items, and using descriptive response options.