Questions to Ask the CIO About Office 365 Adoption

• Executives and board members should exercise due diligence by questioning CIOs about Office 365 adoption plans.
• Many executives have limited experience with IT projects and need additional guidance to ask the right questions.
• Organizations that have a thorough understanding of the risks and benefits of Office 365 adoption are more likely to achieve success and avoid future surprises.

This report provides a series of probing questions that are outside of the normal IT-related discussions that most organizations have when adopting Office 365 or Microsoft 365. These questions will help executives to work with their CIO and ensure plans and estimates are realistic, prior to committing the organization to a multiyear relationship.

Office 365 Overview

Office 365 is a line of desktop software and hosted services for document authoring and collaboration that can replace some on-premises software such as the Office suite and Exchange Server for e-mail.

Organizations adopt Office 365 for a variety of reasons, including reducing the cost of infrastructure management, replacing aging hardware, leveraging Microsoft’s global reach, and helping comply with security and regulatory requirements. Due diligence questions fall into two broad categories: business impact and cost impact.