On a beautiful October morning in 2011, the CEO of a mid-size oil marketing company located in Nairobi, Kenya has to make a tough decision whether to upgrade their current B1 system to a bigger version of SAP. Abbas, the new Information Communications Technology (ICT) Director of Zaidi Group, was worried that Zaidi was building a bigger and bigger company on top of a more and more small enterprise resource planning system. Abbas's fears also include RedLock's past inefficiencies. Kariuki, the Finance Director, on the other hand was into the fear of overspending in a huge information technology (IT)system where current functionalities required can be addressed by a smaller system through add-ons, customization and development. Subject area Decision Analysis, Management Information Systems, Strategic Management, Organizational Development, Financial Management, Risk Management