We discuss an initial research concept for the application of the task-technology fit model to measure the factors that influence the utilization of interactive simulation for executive and managerial training. Interactive simulation is widely used by the military for senior leadership and managerial tasks. Simulation is also used commercially for training similar skills. We propose measuring the task-technology fit of simulation applied to training executive and managerial tasks such as strategy development, decision-making, and operational procedures. This research will empirically test which task and individual characteristics provide a task-technology fit for simulation systems. It will assist in the validation of prior information technology investment and ideally stimulate continued investment. We focus on the use of interactive simulation in the military. We feel that our results can be readily extended to commercial executive and managerial training.