Outdated software systems negatively affect businesses and users on a daily basis. Sometimes, internal issues are minimal (e.g., user interface issues), but too often outdated systems are responsible for millions of dollars in lost business and threaten the security of personal information. This puts companies on the fast track to negative headlines and customer loss. Modernization is challenging. Costs associated with a system overhaul force many companies to choose between keeping customer data safe, internal systems running smoothly, and squeezing as much time as they can from outdated software. Many CIOs weigh the pros and cons of updating systems and determine that a breach would, in fact, be less costly than a modernization project. But less costly to whom? Depending on the type of business, a breach can cost companies millions (or more) in their bank account, and cost their customers. Other CIOs choose a partner to modernize legacy software systems. Sometimes it is still necessary to bring in another resource. Here are nine questions to ask potential modernization vectors from Neil Hartley, director of U.S. Operations for enterprise legacy-to-cloud software company Morphis.