The Certified Public Accountant (CPA)/client paradigm is entering a period of significant transformation as a result of the shifting IT paradigm to cloud-based and mobile computing. This chapter deals with a process for developing and executing one's plan. At a macro level, five key steps need to be addressed to complete the IT planning cycle. These steps are strategy, education, analysis, execution and assessment. The objective of analysis is to conduct a SWOT (strengths, weaknesses, opportunities, and threats) assessment of sorts that assesses your current business model from a workflow efficiency perspective and your overall IT model. This includes hardware, software applications, and both internal and external service providers. Implementing dual monitors is an initiative that can easily be completed in a matter of days, whereas fully integrating a document management system can take months, if not years, to complete. Large or small, the execution of every initiative should follow a consistent pattern.