A tool for evaluating support services may correlate those services with an array of factors that define a business environment and then identify the business services that are most directly correlated to those factors. In exemplary embodiments, a tool may prompt a user for input concerning business issues and objectives; correlate those issues and objectives to a plurality of available software support services such as maintenance, optimization, architecture planning, implementation, administration and systems integration services; select the services that most directly address the particular needs and objectives identified by the user; and calculate a return on investment (ROI) associated with satisfaction of identified business objectives through implementation of the selected support services.