Records and information management, in this exponentially growing technological era, has enjoyed its relevance but has also weakened its competitiveness as organizations seek to search for faster way to access information, make decisions, and ultimately, retain indefinitely everything in cyberspace. This phenomenon and paradigm shift create a disconnect in the retention period assignment as cost for space in the cloud is no longer a deterrent as many CEOs may equate same to the compensation of a records manager. This chapter looks at the strategies that practitioners can employ to address risks. The risk matrix connects the variables legal, control, compliance, and fiduciary deliverables for a sustained salable and winning environment. The coordinated strategies will reposition practitioners and ultimately restructure the change management agenda of the organization. It is experiential and allows practitioners an opportunity to use templates as aids.