Migrating 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 develops a systems-based approach to understanding these risks. We draw examples from one firm migrating to e-operations for offshore oil platforms to increase profitability. The firm recently participated in a facilitated group model building exercise to examine the effects of the migration on the organization, and found several interesting and unanticipated barriers and hazards to the transition. The results of the workshop demonstrate the use of qualitative modeling approaches to complex problems, as well as a method to reduce concern about data confidentiality in security-conscious environments.¹