The 10 Steps to Planning a Successful Microsoft 365 Deployment

Taylor Karl
/ Categories: Resources, Microsoft Office
The 10 Steps to Planning a Successful Microsoft 365 Deployment 2295 0

A failure to plan your Microsoft 365 deployment is a sure plan for a failed deployment, to paraphrase Ben Franklin. 

Best practices are just as applicable in the cloud as they ever were on-prem, so here’s how to approach leveraging them when deploying Microsoft 365. 

More Than You Realize

When most people think about Microsoft 365 Office, they think of Word, Excel, PowerPoint, OneNote, Outlook, and SharePoint. With the deployment of Microsoft 365 Business or Microsoft 365 Enterprise, there are so many more opportunities to help your business work smarter- from data analysis to collaboration and productivity.  The list of available Microsoft 365 apps & products is now far, far longer, including Bookings, OneDrive, Planner, Sway, Teams, Yammer, Power Apps like Automate, Forms, and Power BI, and more. More functionality means more planning. 


As with most things, Stephen Covey’s second habit, “Begin with the End in Mind” absolutely applies. Best practices tell us to examine both the current state of the existing environment, and then carefully define the desired end state. If you don’t know where you’re going, how can you ever map the path to get there? 

Define your goals in the context of your organization, and in terms of each department and user group that will be using your resources. Failure of users to adopt a new system is the reason for three quarters of deployment project failures. If users don’t find value in the new system, they won’t adopt. 

Also, define goals in terms of value to the users, the groups, and the organization, not just features and functions. 

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Begin by defining the current state in greater detail. Carefully document every user. Then identify and define the groups that users are currently assigned to. List every application and workload each of these groups access, along with complete requirements for each. Perform an analysis to determine if there are any applications currently resident on your servers that literally nobody is using. Don’t be surprised if you find some. Apps are often orphaned along the way. 

Inventory all the client endpoint devices all users are using, including complete documentation of configuration, capacities, security measures that are in place, and encryption capability. You may identify some devices that will not be adequately equipped to exist in your Microsoft 365 environment due to security weaknesses. 

10-Step Strategic Plan

This is the phase of your project that you’ll want to focus on and spend the most time and energy on. Get this right, and the rest of the process runs smoothly. 

Start by identifying the deployment planning tools of your preference. The best will always provide detailed, step-by-step advice that goes far beyond the scope of this blog post. Consult your instructors and other resource people at United Training for advice. 

The most important elements of your strategic plan must be: 

1. Planning for Security in the Microsoft 365 environment 

Do not assume that Microsoft 365 itself provides all the security you’ll need. Security must be planned from end-to-end, from each user endpoint device to the network and back. 

2. Avoiding Operational Disruption during the deployment 

Your goal is to have users go home at the end of one day and come back to completely ready new systems the next with no lapse in regular operations. 

3. Contingency Roll-Back Plan if you run into unforeseen obstacles 

Even the best planning may not take every possible circumstance into account. Be sure you can roll back to the current state at any point in the process should you encounter any surprises. 

4. Pilot Deployment (if viable)

It’s always preferable to test your deployment with a small group of users who would be minimally impacted should a failure occur. Great opportunity to learn what potential pitfalls may await. 

5. User Provisioning

Every user will have to have their Microsoft 365 account subscription fully provisioned, fully configured, and ready for use. 

6. Data Migration 

Two little words that could dwarf the entire rest of the process. If you have determined which workloads must be migrated and to where, and identified those that can be archived or discarded, this turns into a great opportunity to clean house. 

7. Post-Deployment Testing

Before a user ever touches their endpoint, you want to be sure their first experience will be fantastic. 

8. User Orientation 

Ideally, users should be shown their new environment before, but as close to the actual transition as possible. This way, they have less time to forget what they were anxious to try out! 

9. Day Zero User Support 

Assuring the optimum user experience is enhanced by having trained, experienced support personnel on hand to assist on that first day back in the new environment. 

10. Ongoing Support 

Your ongoing support plan should be more than just maintenance and problem resolution. It should be a plan to help every user get the most out of Microsoft 365. 

The Proof is in the Pudding 

Any strategic plan is only as good as its execution, or as General Patton said, “Planning without Execution is Hallucination,” but the more detailed and precise your plan, the higher your likelihood of success.