5 Common Planning Mistakes in Cutover Office 365 Migrations

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For organizations planning a cutover Office 365 migration, poor planning can have particularly devastating results. If you face unanticipated errors during the switchover, your organization could experience data loss, disruption to business communication or a host of other errors.

What Is a Cutover Office 365 Migration?

Microsoft defines cutover migrations as a process used to move 2,000 or fewer mailboxes to the cloud in a single batch, though best practices dictate moving a smaller amount at a time. While making the switch to Office 365 can offer improved security, compliance and global access, getting there is often more challenging than many organizations anticipate.

Avoid These Planning Woes in Your Cutover Office 365 Migration

Read on to learn five common cutover migration planning mistakes and how to avoid them.

1. Insufficient Business Continuity Planning

Security issues, loss of data and non-compliance with regulatory standards are nightmares when it comes to business continuity planning. Regardless of your Office 365 migration approach, you should plan to retain archives in accordance with regulatory laws, maintain appropriate information security practices and mitigate the risks of critical information being lost because you used the wrong types of tools or approach.

2. Unanticipated Downtime

Throughout the migration process, careful testing is critical to ensure you don’t face issues after you go live. Examples of problems that can require troubleshooting and testing after a cutover Office 365 migration include:

  • Important emails getting caught by spam filters
  • Problems with global calendaring features syncing consistently
  • Issues integrating on-premises Exchange users with cloud users during batch migrations

While your organization may not face any issues that require testing or troubleshooting, failing to plan for careful functionality testing on go-live day can result in lost communications and other sources of downtime.

3. Unplanned Archival Risks

Your organization likely has a fair amount of archived email data, which can be a necessity to maintain optimal system performance. Failing to plan how you’ll maintain your archives, either on-premises or in the cloud, can lead to non-compliant loss of data or unanticipated delays in the cutover process.

Regardless of where you plan to store your archives, on-premises or in Office 365, putting the right tools into place to automate the migration and mitigate process risk is crucial.

4. A “Big Bang” Approach to Training

It’s tempting to assume that transitioning to Office 365 from on-premises Exchange could be relatively simple for your users. You could be right. However, when confused users compound with projects that don’t go as planned, the result can be a full-scale disaster.

Effective training isn’t always a short-term project, though you can complete a cutover migration relatively quickly. Have IT use Office 365 and onboard designated trainers before migration day to help ease the transition.

5. Underestimating the Size of the Project

If your organization has fewer than 2,000 mailboxes, migrating users shouldn’t be that hard, right? Unfortunately, underestimating the project can lead to some of the greatest business risks associated with a migration, which include:

  • Projects that run well over budget
  • Too little post-migration support
  • Unexpected business disruption

If your organization isn’t planning a migration like a major IT project, you could face one or more of these risks. If your internal resources are minimal, unlocking expert project management support can ensure you remain within budget and user onboarding runs smoothly.

Fast Office 365 Migration Without Risks to Your Business

You can migrate from an on-premises Exchange server to Office 365 relatively quickly. But you shouldn’t underestimate the importance of carefully planning for business continuity, compliance, security, training and testing at each phase.

By working with a Microsoft partner on the project, you can ensure internal and customer communication isn’t lost and you achieve the smoothest transition possible.

Need help mapping out your Office 365 migration strategy? Schedule a risk-free call with Agile IT today.