The current study investigated ways to improve the ecological validity of the neuropsychological assessment of executive functioning through the formal assessment of compensatory strategies and environmental cognitive demands. Results indicated that the group of executive functioning tests (i.e., Trail Making Test, Wisconsin Card Sorting Test, Stroop, and Controlled Oral Word Association Test) accounted for 18–20% of the variance in everyday executive ability as measured by the Dysexecutive Questionnaire and Brock Adaptive Functioning Questionnaire. The addition of extra-test variables significantly increased the variance in everyday executive ability accounted for. The current study adds to the literature on the ecological validity of executive functioning assessment by highlighting the importance of extra-test variables when trying to understand the complex relationship between cognitive testing and real world performance.