Your Office 365 Implementation Checklist - How to plan the switch

You've decided now is the time to move your company’s on-premises content to the cloud. Welcome to the ‘new norm’. 

With the global public cloud service market expected to reach $623.3 billion by 2023 and 83% of enterprise workloads predicted to migrate to the cloud this year, you’ll soon be operating within what Gartner describes as ‘the mainstream.’

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But what's next? Chances are you’ve joined the world’s leading organizations and are turning your attention to Office 365. As the leading cloud vendor worldwide (holding a growing 16.1% share of the SaaS market), Microsoft offers your teams a suite of tools to post enterprise productivity and collaboration, from Delve to Yammer, Power BI to Sway.

Whether you are thinking of going all-in on or opting for hybrid, there’s no denying the Office 365 migration planning process can seem daunting. Thorough planning and step by step execution need to be followed to ensure your company realizes the full potential of the switch. 

If you’re looking to tap into the benefits of cloud-powered content management, check out our O365 breakdown and implementation checklist below:

What is Office 365 migration? 

Office 365 migration is where a company's data and content is securely moved from on-premise services to Microsoft’s online services.

Traditionally, O365 migration plans sat with the IT department; however, today any user registered with a business account can follow Microsoft’s intuitive and automated process to contribute to the transition. 

For companies currently managing content via Google Suite, Microsoft recently rolled out its G Suite migration tool, enabling direct migration of emails, calendars and contacts from Google Suite to Office 365. You can find an in-depth G Suite migration to Office 365 checklist on Microsoft’s blog.

While the transition has incredible potential to increase enterprise productivity, communication and collaboration (while significantly cutting IT spend), a stress-free implementation is no small feat. It takes smart planning, deliberate decisions and time. 

Fortunately, there are several things you can do to hedge your bets and fine-tune the workflow for the deployment. Below you’ll find our Office 365 implementation checklist designed to make deployment planning and implementation go as smooth as possible.


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Areas to consider before getting started with your Office 365 implementation checklist.

Who is in your migration team?

One of the biggest pitfalls of implementation roadmaps is leaving all planning and execution to your IT team. Any O365 migration project plan needs to involve members of each of your departments at all stages

This doesn’t mean that IT can’t take ownership of the Microsoft Office 365 migration project plan. But to assure all critical documents, information and files are covered in your plan, your migration team needs to be made up of people who know their workflows inside-out.  

Assigning roles to representatives from each department also ensures employees across your whole organization are kept up-to-date at important stages of the O365 implementation plan and know who they can talk to about what is being moved and how to access it.


Have you set enough time aside for your Office 365 implementation plan

Businesses often underestimate how much content their employees create on a daily, let alone monthly or annual basis. Unless you’re a two-person company, you should expect your migration plan/template to be lengthy and your migration project to require sufficient resources. 

As you would with any other project, start planning your Microsoft 365 implementation by creating a set of priorities and objectives to get the ball rolling.   

Don’t tackle all your entire implementation project/plan at once. Instead, break up the migration project plan/template into different workstreams with dedicated timeframes. Liaising with your department representatives, start with the most urgent files (usually the most recently produced) and work backward to content that can be archived. 

Consider your implementation timeline carefully. Factor in enough time to properly plan, prepare, and push the move through. However, don’t necessarily think of the individual migration phases of your migration template as self-contained stages. Tasks may occur simultaneously or sometimes overlap.


Do you have a contingency plan in place?

Particularly if you’re following an Office 365 implementation checklist meticulously, your migration could be almost seamless. However, it’s always best to troubleshoot any scenarios where employees may temporarily lose access to the content they need.

If you’ve underestimated the scale of your migration proposal or your IT systems aren’t able to cope with the size of data imports, you risk experiencing network crashes or poor internet connectivity. 

For Office 365 implementation best practice, send employees a heads up email that work is in progress and they may experience short-term issues while you adjust your batch size or upgrade your bandwidth. Give everyone enough time to organize their workload so there is minimal disruption to their day-to-day.


Have you considered the varying preferences and requirements within your organization?

Before you begin the O365 implementation process, it’s important your project scopes out which O365 applications suit the different target groups in your organization

There are three groups to consider with the application strategy:

1. Individual employees 

Individuals must be offered the applications which are intuitive and help them work efficiently daily.

2. Teams or departments

Applications for collaboration and communication must be considered depending on various factors, including preferences across teams.

3. The organization as a whole

Knowledge sharing organization-wide requires applications that can support the organization’s digital workplace. Tools must support an enterprise's needs and integrate seamlessly into existing IT setups. 

Once you’re confident you've carefully considered these pre-Office implementation factors, it’s time to start ticking off tasks on your implementation checklist.

Phase 1: Plan on how to implement Office 365

Begin your O365 implementation project plan by collecting information about your current IT environment. Effective deployment plans can’t be created without fully understanding why you’re migrating and what needs to happen during the switch.


Get everyone on board

Schedule an “Implement Office 365” kickoff meeting to familiarize your deployment team members with the overall goals and scope of the project. Use this meeting to clarify and communicate responsibilities.


Discover your IT infrastructure   

A major step in your pre-migration checklist is to collect facts and figures about your existing IT environment to understand the technology solutions implemented by your company. Check if your on-premises environment meets the requirements for the setup by considering these areas:

    1. Servers and components  
    2. Network architecture and DNS  
    3. Authentication solutions  
    4. Directory design  
    5. Bandwidth  
    6. Mail routing  
    7. Certificates  
    8. Hardware and software  
    9. Mail and other client applications  
    10. Mail archiving and compliance  

Microsoft provides automated Office 365 readiness checks to determine if your on-premises environment meets its requirements and informs you of any issues that might impede your Office 365 deployment checklist.

Another source of support for implementation is the Microsoft Assessment and Planning (MAP) toolkit. Offered as an automated, multi-product planning and assessment tool, it delivers detailed readiness assessment reports, along with comprehensive hardware and software information, and actionable advice to help you speed up your IT infrastructure planning process and collect more information on assets residing within your current on-premises environment.

  • Strategize your email migration project
    Plan ahead and evaluate if you need to purchase any third-party email migration toolsets and check on hardware requirements.  
  • Assess mailbox size and item counts
    Identify the size of mailboxes and the number of items in mailboxes that you will migrate to Office 365 (consider mailbox size and item count and available network bandwidth).
  • Identify existing business-related content that needs to be migrated
    Decide which files, folders, and other content need to be moved. If you plan to migrate Office templates, be aware that upgrading your Office client could lead to file format changes and issues when trying to launch built-in macros in a template. 
  • Learn about different options for user identity and account provisioning 
    Office 365 provides several mechanisms to add employees to the service and manage user accounts.  
  • Define your email coexistence strategy 
    For companies with Exchange Server environments, Exchange online migration project plans are made easy by email coexistence, a key feature offered by Office 365. Email coexistence allows a connection to be established between the on-premises environment and Exchange Online. 
  • Test network bandwidth 
    Test the bandwidth of your company network to calculate migration velocity.  
  • Choose your mobile platforms 
    Plan for any changes required to the mobile platforms used by your company. Exchange migration to Office 365 checklists need to ensure Microsoft Exchange ActiveSync is allowing employees to synchronize their mobile devices with their Exchange Online mailboxes.
  • Work a communications plan into your Office 365 strategy
    Documents or emails that simply alert employees to your switch aren’t going to go far enough to secure user adoption. You need to schedule regular digital and in-person alerts to inform them when they need to start working with Office 365 and provide clear instructions showing how to make the most of their switch to the cloud.

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Phase 2: Prepare your move to Office 365 

In the second phase of the O365 project plan, the implementation checklist items focus on cleaning up your on-premises environment to prepare for migration. 

Again, remember this phase of your Office 365 transition checklist shouldn’t be siloed to the IT departments in your company. Office implementations work much better if representatives from different departments are involved.

  • Add and verify your domain name
    First up for phase two of your checklist, add your domain through the Microsoft Online Services Portal and create the DNS records to route domain traffic to Office 365.
  • Clean up your on-premises Active Directory for synchronization
    Prepare your on-premises Active Directory (and update, if necessary) for synchronization with Office 365.
  • Enable single sign-on
    Install and configure identity federation servers on-premises and activate the single sign-on service.
  • Install the Directory Synchronization Tool and synchronize
    Install and configure Directory synchronization servers on-premises and activate Directory synchronization to provision user accounts if your Exchange to Office 365 migration project plan is hybrid in its nature

Editors note: Read everything you need to know about Azure AD and Passthrough authentication here.

  • Configure your email coexistence 
    Install and configure Exchange hybrid servers on-premises to enable communication between your existing Exchange servers and Exchange Online. 
  • Activate your Sharepoint online rollout plan 
    Ensure your deployment project plans ahead for the deployment of any custom SharePoint solutions. Your O365 Sharepoint implementation plan should also cover the migration of existing SharePoint content.
  • Configure Online IM services
    Configure domain federation and public IM connectivity settings to boost your network for conferencing.
  • Install client applications and desktop setup
    Last up on phase two of your O365 checklist is to determine if client applications are properly updated and configured for Office 365. 

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Phase 3: Take the final steps in your O365 migration checklist

The final phase in your deployment planning checklist involves moving mailboxes and business-related content from your on-premises environment to Office 365. It's a common pitfall for an O365 implementation guide to lack a content strategy. This is often caused by rushed or incomplete pre-migration audits. 

Remind your department representatives that this is a great opportunity for your teams to clean up their data, meaning only relevant content is migrated. Within your scope of work, get employees to tidy up their mailboxes, archive libraries and delete irrelevant files. If you need an incentive, just remember that the more information your business has, the longer and more complex your O365 migration project plan will be. 

Be sure to plan which content needs to be moved, and include these vital steps on your implementation checklist:

    • Assign licenses
      If you have not already done so, assign licenses to employees through the Microsoft Online Services Portal to grant access to Office 365. Enable Exchange Online, SharePoint Online, and Online IM services.
    • Inform staff about the final phase of your project
      Plan office education sessions that update employees on when the migration is going to happen, how long the process will take, and what they need to do to switch to the new platform.
    • Migrate mailboxes
      Use your selected Exchange migration tools or third-party solutions to migrate to Exchange Online. To boost migration velocity of mailbox content, you may need to reduce the size of mailboxes.
    • Move existing files and folders
      Use third-party migration tools to move existing Office documents and templates from your current on-premises environment to Office 365.
    • Change DNS records 
      Once you have completed all migrations, change your DNS records to your domain registrar. 
    • Configure mobile phones and devices for Office 365 
      Set up user mobile phones along with any other mobile devices to access emails and Office documents on the go. Alternatively, email migration, plans/templates should set out clear instructions to employees on how to connect from their mobile devices. Remember: to launch corporate templates through Office 365 on mobile devices, you may need to rethink your template management approach, especially if your Office templates contain VBA code. 
    • Factor post-migration service testing into your O365 implementation roadmap
      After migrations are completed, perform full-scale testing of the service functionality. Your Office 365 test plan should make sure all your plug-ins have transferred over. If not, your need to ensure your testing checklist covers a reinstallation process.
    • Check your Office templates work in Office 365
      Test cases or scenarios where your most important Office templates will be used. See if the templates launch correctly and examine whether there have been any changes in style and formatting. If some of your Office templates link to other Office files or integrate with CRM or ERP systems, test those connections too.
  • Add email signatures
    Email signatures don’t always migrate easily. Check yours and add a new one if required. 
  • Stay secure
    Check all your content is protected by your new security system and you’ve set the correct permission settings for individuals departments and employees.

Read next: Emails in the cloud: Office 365 Exchange Online migration checklist

Beyond your Office 365 implementation guide: the post-migration plan

Finally, it's important to consider what to do post-migration, a vital area that some implementation checklists overlook or fail to consider. 


Set a deadline for using old systems

A successful Office 365 rollout plan can only be achieved if all employees are using your new platform. If people are still working with your old system and the new, it’s likely that out-dated brand assets and old templates will be used and documents will be overwritten or go missing. 

By setting a cut off date for the use of old or legacy systems, you’re ensuring no employee is left behind. Migration efforts are safeguarded and everyone enterprise-wide will benefit from your Office 365 project.


Plan ongoing and extensive training

A major reason employees could be tempted to switch back to old ways of working (and undo the investment you’ve placed in your rollout project plan) is a lack of training. Don’t, as McKinsey warns, just “lift and shift.” You can’t assume that employees will simply log in and become pros. Even the most clued up users may not be aware of the huge range of in-built tools and features that Microsoft offers. 

Start with the basics to test out employees’ Office 365 readiness. Checklist items under category would include how to navigate the new interface, where to access important and regularly used files and a thorough run-through of Exchange. Then, carry on consistent and ongoing training sessions to introduce new features and tools, emphasizing how each will benefit the employee: from saving time creating a document to improving consistency of their output. 

Although Microsoft automatically alerts users to new features and provides accompanying guides and prompts, those managing your Office 365 onboarding checklist should keep an eye out for new updates and monitor user adoption. You want your teams to be progressing with the platform rather than settling for what they know.

Realize the full potential of your investment 

With content fully migrated, you’re now in a great position to capitalize on additional Microsoft business products associated with O365. 

In their recent report on the evolving nature of one of these products, Microsoft Dynamics, Forrester identified the tool’s ability to entirely ‘reimagine business processes’ by giving enterprises deeper access to insights, data extraction and growth areas within their organization. 

With the likes of Avanade, HCL Technologies, and PwC already profiting from innovative services within the Microsoft Dynamics market, it’s clear there’s a lot up for grabs within Microsoft’s evolving product landscape, particularly in regards to consulting and IP solutions - an exciting prospect for both vendors and clients operating in Microsoft’s cloud-hosted environment.

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