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Deploying Microsoft 365 (formerly Office 365) can be exponentially complex at enterprise scale. Conveniently subscribing to multiple services bundled with a single license can turn into years of organizational technical debt. This presents a considerable challenge to clearly understand and effectively plan for the migration to Microsoft 365 (M365).

The key is to recognize a M365 migration as the employee-centric transformational program that it is, and to plan accordingly. Let's discuss a few (but not all) key areas requiring attention before you get started.

Core services

Most organizations, large and small, employ Microsoft Exchange email and shared or cloud-based file management. With M365, all these services are commonly bundled into a single integrated suite of services, including:

  • Exchange Online (Web), and Outlook Mobile;
  • SharePoint Online;
  • Teams;
  • Endpoint Management;
  • security & compliance components; and
  • OneDrive.

Organizations elect to move to M365 for several reasons, including enhanced security, service management efficiencies and improved user satisfaction; however, specific attention must be afforded to how current disparate communication and collaboration services are migrated to the M365 Core Services.

The Azure landing zone

What does your multicloud architecture look like, specifically the Azure component? There is both a technology aspect to this, as well as a review of Microsoft agreements. Your organization will want to be sure to maximize utility of this key item and ensure proper alignment of components such as SharePoint and OneDrive, enhanced cloud-based security improvements with the current on-premise infrastructure and services. 

Don't forget to review governance and compliance which covers data classification, identity and access management, application level and network controls. There is a wealth of materials available to educate and test readiness in this space.

Directory services

Too frequently, the move to M365 is the point at which organizations realize they have issues with their Active Directory forest. Years of unresolved M&A activity, or ad-hoc expansion into multiple geographic regions, acquisitions, divestitures or simply outdated operational practices have the potential to impact the user experience downstream if not resolved up front.

Proper synchronization of AD to the Azure landing zone is a "pass/fail" issue to successful migration and can halt a program before it gets off the ground. Once again, proper preparation and testing will help to resolve issues before they occur.

Network impact

Implementation of M365 at enterprise scale will fundamentally change the interaction of end users with the data center. Rather than having email, shared files and other services bottleneck through standard WAN connections, users will instead connect directly to the cloud from the work office and home office. 

Indeed, this is the very premise of cloud computing: understanding where the data currently resides and using models and labs to predict what will happen in a future state are prerequisites to beginning the program. Any network changes required to respond will require additional planning and implementation time, so a network assessment should be considered early enough to positively impact the migration program.

Incompatibility everywhere

A full implementation program of Microsoft 365 would include Teams and SharePoint. In fact, as of the 1902 build in January 2020, Teams is included and will be part of the ecosystem. Each of these platforms comes with its own compatibility challenges:

  • As a collaboration platform, Teams adoption may require a detailed look at compatible headsets and conference room equipment, with resulting changes or updates.
  • It is likely that Teams will coexist with other collaboration platforms for some time, such as WebEx, Zoom and Slack. Proper understanding and planning can ensure a smoother adoption and a happier user base. Getting in front of the technologies at play and knowing what it will take to integrate them will avoid mid-flight issues later.
  • If an organization has been using Skype for Business extensively, Microsoft Teams is the next-generation collaboration platform. Here it will be necessary to understand any voice gateways currently in place, prior to any switch. This is another commonly overlooked area.
  • Enterprise organizations have SharePoint sites in a deprecated or dark state. Those that were early adopters may have a considerable amount of this technology debt to resolve before migrations can be completed. This in and of itself may not impede actual migration, however, expected expense relief may not come until these issues are resolved. Once again, getting in front of version or inactive site issues will spawn needed sub-projects to determine legacy site disposition.

Endpoint impact

An endpoint is any device that is physically an endpoint on a network (e.g. servers, desktops/laptops, mobile devices, etc.). Endpoints can also be considered a set of destination IP addresses, URLs for M365 traffic and domain names. All these endpoints, whether physical or virtual, require thorough assessment and planning prior to any M365 deployments and/or migrations depending on your transformational project's scope.

If overlooked, the intended security enhancements and positive experience expectations, established across IT leadership and organizational staff, will be missed.


Often overlooked is the planning around licenses. Are you considering buying E5 or EMS licenses?  That expense adds up quickly. An assessment into whether users need Kiosk or enterprise-based licensing really depends on the use case.

Ready to start the journey?

Microsoft 365 is the one application suite that will literally touch everyone in the organization, from the CEO to new employees. The most important factor is to not underestimate the breadth of the change and to plan accordingly at all levels—in the lab, in the data center and most importantly, where the impact will be felt: enabling the end users. An "ounce of prevention" in this space will be worth many "pounds of cure."

Are you ready to improve productivity, teamwork and employee satisfaction? Reach out to us to get started.