Previous research clearly demonstrates that expertise is directly related to the accumulated amount of deliberate practice, a training technique which allows knowledge to be encoded around key domain-related concepts and solution procedures, thereby facilitating rapid and reliable information retrieval (Ericsson, Krampfe & Tesch-Romer, 1993; Ericsson & Lehman, 1996). Until recently, there have been very few computer-based training programs that leverage the deliberate practice approach for training higher-order skills such as leadership, situation awareness, and decision-making. In this paper, the authors present interim training evaluation results from two such training efforts. These include Wisdom: Lessons Learned from Operation Iraqi Freedomâ„¢, which focuses on small unit Army leadership skills in Support, Stability, Transition, and Reconstruction (SSTR) operations, and IMPACT: Team Skills Training for the Dynamic Targeting Cellâ„¢, which focuses on Air Force leadership, teamwork, and decision-making skills in Dynamic Targeting Cell (DTC) operations. Quantitative and qualitative results suggest that both training programs produce practically and statistically significant gains in learning and self-efficacy. The results also suggest that the training programs are perceived as being practical and operationally relevant. Implications for low-fidelity simulations, in general, and deliberate practice-based simulations, in particular, are offered.