LAE Software Notes From The Field: Microsoft 365 Migration Roadblocks

LAE Software Notes From The Field: Microsoft 365 Migration Roadblocks

As we come to the close of 2020, it’s been ten years since the formal launch of Microsoft 365 (released as Office 365 on June 28th, 2011 and renamed to Microsoft 365 on April 21st of this year). While many millions of on-prem accounts and petabytes of data have been migrated over this time, numerous organizations are still in the process of migrating or have yet to begin. For these late adopters to the Microsoft cloud platform, there have been numerous lessons learned, which now present a perfect opportunity to take advantage of those who have gone before. Moving data and digital assets, in general, is no trivial task, and hopefully it comes as no surprise that proper planning and preparation are vital to migrating to Microsoft 365. Here are some of the main roadblocks encountered by organizations and how to side-step them:

#1 Not addressing identity first

Have an Active Directory that hasn’t been checked over in years since “it’s just been working”? Using another identity platform and hoping that “it just works”? One of the first roadblocks or hurdles encountered by migration consultants is a “dirty” or - to put it nicer - “less than optimal” directory. For Microsoft Active Directory, there are tools such as IdFix ( that can discover and remediate identity objects for you. Take the time to review your identity infrastructure (or have it reviewed) before starting your migration.

#2 Incomplete understanding of current email and data environment

While no one wants to admit it openly, many organizations aren’t familiar with essential pieces of information such as:

  • How much email and file data do they currently have (mailbox sizes, share folders, etc.)?
    • Does all data require migration?
    • Does the organization understand how long it will take to migrate?
  • Where the data is located (databases, PST files, Public Folders, etc.)?
  • Are your email and data systems healthy?

An inventory of your email and data is a critical starting point for planning a migration; many times, this is missed or skipping in rushing to move to migration instead of designing a proper migration approach.

#3 Integrations, integrations, integrations!

Many email and data platforms are standalone systems, which is ideal for when migrations and changes are needed. However, in the wonderful world of technology solutions we live in, software that integrates and extends the functions of email and data services are plentiful… which is terrific, until we need to migrate. Not taking the time to understand the impact that these software integrations present is another all-to-common roadblock when migrating to Microsoft 365.

Specifically, the following details must be known for the integrations:

  • Is the software still being used?
  • Who in the organization is using it?
  • How does it affect their business workflow?
  • Is it under a support contract?
  • Does it support working natively with Microsoft 365?
  • Does the current version work with Microsoft 365 or will another version or product be needed instead?
  • What are the technical and business impacts from downtime of these software packages?

While there are many more potential roadblocks to a successful – and uneventful – migration to Microsoft 365, these three areas represent 90% of the issues that can be avoided with proper preparation and planning.

Happy Migrating!