Many older adults reside in assisted living communities due to increased difficulty managing health conditions or performing activities of daily living (e.g., bathing, toileting, walking). A primary goal of assisted living communities is to help residents maintain their health and well-being. One method by which this is accomplished is that caregivers continually monitor residents for cues that might signal problems or concerns, and then respond appropriately. However, very little is known about this form of decision making done by caregivers working with assisted living residents, including whether decision making changes with increasing experience. To investigate these questions, direct care workers from assisted living facilities took part in a scenario-based interview during which they responded to hypothetical care situations with older residents. The explanations participants generated for the various scenarios were classified as either general or specific, with the majority of explanations coded as specific. Specific explanations were primarily that the situation was the result of a physical health issue. The type and number of explanations varied widely from scenario to scenario. Lastly, the data from the current study did not reveal consistent differences between the two levels of experience that were examined. This research has implications for the design of future training programs for direct care workers and also highlights the potential need for decision support systems in this domain.