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How to Migrate to Office 365

Jul 3, 2019 by Mike Weaver

This post is an edited transcript of my video “How to Migrate to Office 365”

Here at Quadrotech, we help organizations migrate to the cloud. In this blog, we’re going to talk about the steps organizations need to take to both prepare and move into Office 365. When it comes to adopting new technology in your organization it comes down to 3 major steps. The first is planning, the second is execution and the third is ongoing maintenance. Today, we’re going to talk about those 3 steps and what you need to do for a successful Office 365 migration project.

Planning your Migration to Office 365

So, let’s talk about planning your migration into Office 365. This should take high priority because it outlines the infrastructure of your project and ensures everything runs smoothly. Here, you need to ensure that you’ve completed some initial tasks and follow the ‘Plan: Checklist’ below. Firstly, start by ensuring you meet all the prerequisites for your migration. Then, you may have to do some remediation, which we’ll delve deeper into later in this article. Lastly, you need to plan what workloads are going to move into the service. The most common service is email, almost every organization I’ve spoken to who migrated to Office 365 have also moved their Exchange.

That said, there are also other services to talk about here. For example, with SharePoint, you might have been on an on-premises SharePoint environment, or you may have some network sharers that you want to move to SharePoint, meaning it’s essential you include that in your plan as well. User file shares are another very important piece of the planning because you’ll need to allocate time and resources for moving that data into OneDrive for business.

Let’s talk about more aspects to the planning phase, during this process you’re going to need to review:

  • Your infrastructure
  • The versions of all the software that you’re running
  • Your Office 365 minimum requirements.

During setup, you’ll need to meet with specific requirements to use certain migration features. Another aspect of the migration that you need to plan for is identity management. How are you going to manage Active Directory IDs during your migration after the migration? For smaller organizations, you may choose to move to an entire cloud-based Active Directory system. This decision will then allow you to turn off your on-premises Active Directory servers. Larger organizations are typically going to do a hybrid setup, which also has certain requirements that you must meet.

One of the most important things that you can do today, even in early planning, is use a tool called ID fix which is provided by Microsoft. This tool will go through in a read-only fashion, look at your directory and see if there’s any work that you need to do to prepare. Some of this work may be difficult or take a long time, so it’s important to do this process as soon as possible so you can plan precisely.One prerequisite that you’re also going to have to address when you’re migrating Microsoft Exchange is ensuring that your on-premises Microsoft Exchange environment is at minimum levels. You may or may not be able to use all the migration options that are available to migrate into Office 365.

In some cases, you may need to use third-party products only because you won’t be able to directly move from your version of Exchange Online. There are two main aspects of planning when it comes to doing your Exchange Online migration. Are you going to do one large cutover migration or migration batches? Or, migration waves, if you’re an organization with less than a thousand users, but maybe more than 500 users, your kind of in-between both categories where you may be uncomfortable doing a large cutover migration, but you really could, if you needed to do that, over a long weekend.

If you’re an organization with more than a thousand users, a stage migration is the best option for you. You really don’t have the staff typically to deal with user issues mobile device reconfigurations and things like that for a very large cutover migration. So, most organizations who have a thousand users and up are going to do stage migrations.

We also have a great blog on how to group in wave users which can help to guide you to identify dependencies in your organization and ensure that you’re moving to Exchange Online with minimal interruption.

Another aspect of planning that some organizations stumble on is looking at your network topology and bandwidth need. Today, if you have on-premises Microsoft Exchange and file servers, your users are coming directly into your data center to look at these files and their email, however, going forward, they’re going to the cloud service. Some organizations focus during a migration on just the bandwidth needed to migrate data into the service, but what they lose track of is the topology completely changes when you’re in a cloud system. Now your endpoints need to be able to get out to the internet and the space quickly and effectively. Some organizations may need to make bandwidth changes or alter their agreements with their network providers to ensure that there’s enough bandwidth for the users to communicate with the cloud.


The final aspect of planning is pilots, a pilot is an essential part of any IT project and this is no different. You really want to do an end-to-end migration with a good chunk of users. Obviously, to begin with, you’ll want to start with just a few, but then you can gradually move to 50-100 user business pilots and practice every aspect of this. This includes end-user communications, ensuring that the endpoint points to the new system, running through the mobile device configuration and really collecting feedback and seeing where you can improve your process.

The great news is a lot of organizations have moved to Office 365 from their on-prem systems before you, so the trail has really been well set on how to do this. But every organization is different, so you really want to ensure that you do a great pilot with your users, so you have a successful outcome in your project.

What’s interesting is when you do a migration into Office 365, the migration itself is actually one of the easiest aspects of it. When we look at all the planning that goes into the project, when you hit the migration phase you just have to execute your plan, however, you also want to ensure that you’re keeping on task and don’t get fatigued in your project. For larger projects, mistakes can be made because we abandoned our plan, or we keep changing the plan that we spent so much time on. It’s really important that you either have a good project manager, or a really good discipline to stay on the plan that you have.

A great example is you may agree to use 500 users a week for your migration metric, and then you keep creeping in 50 more users and then suddenly, you realize something breaks in the process, for example, maybe there’s too much help desk volume on Monday morning for users needing assistance. Things like that can creep in, and it really can cause problems in your project and put a pause on it when you have an organization slip, so you really want to ensure that you stick to your plan and execute it as you designed it.

Tools available for migrating to Office 365

The other aspect of migration we’re going to talk about is what tool we’re going to use. During the planning phase, it’s likely you looked at the free tools provided by Microsoft, and some third-party pools like the solutions Quadrotech provides. Regardless of the option that you choose, you want to test these and ensure that they meet your needs, are getting the desired throughput and minimal disruption to your users.

The other important concept of migration is choosing a solution where you can pre-move as much data as possible. Depending on your organization, you may have a lot of data depending on what the quotas are and how much data users have. It may not be possible to move 500 users in one weekend, so you want to pre-stage and pre-move as much data as possible. The good news is most technology including some of the free tools provided by Microsoft and third-party tools allow you to pre-move the bulk of the data in advance, that allows you to switch a lot of users at once over the weekend, so you can hit your 500-750 user migration goal.

The other aspect of migration are things other than email, we’ve spent a lot of time in this talking about email.  But there are other aspects including PST files and that can be a really difficult project from identifying where they are, who they belong to, and migrating them effectively without user impact. That’s something we have a great blog series on as well, “How to Migrate PST Files to Office 365” and certainly something to look into.

Another aspect can be an archive system for email or files, which are also worth moving into Office 365 during your migration to get a full return on your investment of the cloud service. Looking at options to move those can be really tiresome, and sometimes be a project in itself. So it’s important that you utilize automation in your project because if you’re going to move users from Exchange into Office 365 and you have an archive system, you want to do those projects together, automation can help tie these projects together to save a lot of time and keep your project on track.

Migration completed. What’s next?

Now you’re in Office 365, you’ve got everybody moved and you need to manage the environment. Likely with your on-prem system, you had a lot of tools and processes that you built in to manage your environment. But suddenly with the migration, those tools will not work anymore and very quickly, you’ll find yourself in a hole in the ability to manage your environment. It’s important that you look for reporting solutions that look at not just usage information, but also making sense out of the audit log so you can protect your information. Microsoft have done a great job of hardening the walls of 365 and keeping your data secure, but there are still threats with social engineering and other issues that you want to be aware of.

Ongoing Maintenance

Quadrotech’s tools enable you to swiftly get these reporting capabilities back and more. The solution can not only provide you with usage and device information but also detects threats to your environment using our security and audit module. This allows you to keep track of what users are doing, find threats and react to them as needed. The other aspect can be automation, some major problems you may experience as you move to Office 365 is automation around managing the environment. For example, the tools your helpdesk used to help your users may have also changed during the migration and now need to be recovered.

Quadrotech also provides solutions to help organizations manage their Office 365 environment, enabling more users to do their jobs and make effective delegated administration decisions. For example, you may not want a first-line helpdesk operator to have global administrator rights, but there might be some aspects of permissions that require those rights for them to do their functions. You can delegate these tasks down a fully compliant and audited manner so that the helpdesk member can be enabled at the first level. Users love it when they get their problem solved there and then, meaning your organization can be more efficient and your helpdesk will reap in the benefits from having a high first contact resolution rates.