10 Steps for a Successful Office 365 Migration Plan

Office 365, rebranded in 2020 as Microsoft 365, offers more flexible and timely access to the robust programs available for professional and personal use than its earlier iteration. Microsoft 365 allows the user to move from office to home, anywhere in between, with access to the same programs and files in any location. In today’s new world of working remotely, this flexibility is key.

One of the most appealing components of Microsoft 365 is the powerful email capability in Microsoft Outlook. Outlook now has additional functionality as a streamlined app that includes Outlook Mail, Outlook Calendar, Outlook People, and Outlook Tasks, offering task management, a calendar application, and a contacts manager that is included with business and enterprise Office 365 subscriptions.

Although upgrading your business to Microsoft 365 may be appealing on many levels, where to start may seem daunting. Here is our list of steps that your IT support team can take to make the process run smoothly.

10 Key Steps to 365 Migration

  1. Start with a Roadmap

Understanding your organization’s needs is critical to the preparation for the migration to Microsoft 365. Your IT experts should be asking how the system will be used, what files will be migrated, and who will be able to access the information. How will you use the system to encourage collaboration between various departments or divisions? Will your team be using it predominantly for email, for storing files, or will Teams also be utilized for messaging or virtual meetings? Understanding the full scope of how your organization can and will use it will help your IT team better prepare everyone for the migration.

  1. Choose Your Method

Depending on the size and infrastructure of your organization, there are different methods your IT support team can choose from for the transition. The amount of data to be moved is one of the biggest factors – the larger the business, the bigger the challenge. Smaller companies have an easier transition, but large or small, know that choosing the right method can avoid difficulties in the transition process. There are three methods to consider.

  • Cutover Migration – this method is best for small- to medium-sized companies with 1,000 or fewer mailboxes. The mail migration is done all at once, so it may not suit larger companies that need to do a more gradual migration.
  • IMAP Migration – this method will migrate the mailboxes only, so unless you are only managing email, your IT experts may want to opt for a different method.
  • Hybrid Migration works for companies of all sizes. This method is the most complex and will require IT experts to navigate. A hybrid exchange server is created to establish a connection between the organization’s local server and the 365 server. This method is the most effective for large companies.


  1. Build the Road AND the Warehouse

Once the method is chosen, you or our IT support team will need to confirm that your company’s infrastructure is ready. You are building the “road” to the transition, and the “warehouse,” in this case that would be Microsoft 365, to make the transition happen. Make sure you have strong server management in places, such as Active Directory Federation Services, or Okta, to allow the performance of necessary administrative functions during the mailbox migration process. Virtual options are also available, but in general, the larger your business is, the stronger the hardware and resources should be for a smooth transition.

  1. Early Testing is Key

Migration time varies based on your organization’s size and needs, but the process is always time-consuming. Before starting the migration process, testing is key to your IT team avoiding major headaches once the process has begun. A good test involves migrating test emails to determine their functionality’s success or failure, thereby discovering early problems with the migration process.

  1. Establish Guidelines

Establishing guidelines based on how your employees will use 365 will help in creating and maintaining a good recordkeeping process and security protocols. Knowing how your users will send messages and how they prefer to store them will help your IT support establish a solid record-keeping strategy. Knowing which programs are used most on a normal day is another important measurement to consider. In other words, before the migration begins, it’s critical to know how Microsoft 365 will be used most effectively in your work environment.

  1. Know What Version of Exchange You Use

If your business is using an older version of Exchange, updating to the newest version is important to the success of your migration. With older versions, such as Exchange 2003/2007, moving to 365 may cause the loss of important mail services. Your IT tea should update Exchange before they begin to prevent the migration from taking longer than expected.

  1. Use Office 365 Health for a Check-Up on Your Infrastructure

You’ve prepared your staff and your servers for the migration, but you’re not ready to press GO yet. It’s critical to make sure your infrastructure is also ready. Office 365 Health is there to help. The program does comprehensive testing to make sure that each component of your migration process is ready. There are two choices in running the health program, a quick check or a complete check. The latter is more time-consuming but more thorough. Your IT team should complete this process – or a similar version – before they start the mail migration. Consider it mandatory!

  1. Now Check the Compatibility

Making sure Outlook and other applications will be compatible with Microsoft 365 is an important next step. Outlook has various older versions. Some are compatible with 365, and some or not. Make sure that the version you are running will be compatible before you begin.

  1. Resources That Can Help

There are many resources available to assist your IT team in the migration process. Microsoft offers free tools such as a readiness tool and Exchange Server Deployment Assistant. There are also outside resources such as MetaLogix and Sharegate as well as external experts who specialize in these migrations.

  1. Go Time

Now that you have a plan and you have done the necessary checks, the final step is deciding what type of migration you will choose. Staged migrations allow critical services to remain available to administrators and management and are recommended over migrating email services all at once. During a staged migration, Microsoft 365 will even work with your Exchange servers, but it is best to complete the transition to 365 to avoid compatibility issues down the road. If your company has multiple servers, expect increased complexity with compatibility and maintaining infrastructure during the transition.

Now it is go time. Once you have decided on what method you will use for the migration, your IT team can start the transition. Setting it up correctly is key, so take your time. Adequate planning will help prevent unnecessary downtime or having to restart the transition.

Final Suggestions

  • Communicate clearly to staff about why your organization is moving to Microsoft 365 and the benefits of the move.
  • Understand how your workforce will best use Microsoft 365.
  • Create a record-keeping system once the migration is complete and include backup strategies if necessary.
  • Use one-click sign-ins to make it easier for your employees to adapt to the new system.
  • Make sure that any additional customizing you do is compatible with Microsoft 365 to avoid any service disruption.

In conclusion, there is no doubt that upgrading a company system, especially involving email, is a massive project. But the reward of using a system like Microsoft 365 is worth the effort. This cloud-based option allows for successful integration between email, programs, and management solutions, creating greater efficiency and flexibility for the organization as a whole.

Want to know more about how to migrate to Microsoft 365? Visit us at Dyrand for more information, or to get an assessment.