Software engineering practices have experienced significant changes over the period of past two decades. Keeping in view the competitive market trends, now is the high time for many organizations to shift from traditional waterfall models to more agile technologies like Scrum [22][23]. A change of this magnitude is often not easy to undertake. The reason that both software engineering techniques are different in many respects, organizations require considerable amount of analysis of the whole transitioning process and possible scenarios that may occur along the way. Small and medium organizations are normally very skeptical to the change of this magnitude. The scale of change is not limited to only software processes, in fact, difficult part is to deal with old attitudes and thinking processes and mold them for the new agile based Scrum development. The process of change therefore need to be understood in the first place and then carefully forwarded to the implementation phase.