Abstract: Migrations to new modes of operation are perilous times for most organizations. For firms that routinely work in high-threat, high-reward situations, the risks of innovation are particularly challenging. This paper presents a systems-based approach to understanding these risks, drawing examples from one firm migrating to e-Operations for offshore oil platforms to increase profitability. The firm recently participated in two facilitated group model building exercises to examine the effects of the migration on the organization and resources needed to safely implement multiple changes over time. Based on these exercises, a simulation model of the timing and relative levels of risk, was developed. The results of the workshop and simulation demonstrate the effect of a combined qualitative and quantitative modeling approach to understanding complex problems.