Office 365 migration checklist

In this blog post I’ll cover the steps you should go through as you’re planning to move.  

Put someone in charge of the Office 365 migration 

The most important piece of a successful Office 365 migration is good leadership. While this blog post will focus mainly on SharePoint Online, Office 365 is a big suite of intertwined applications, and for your SharePoint Online migration to not end in frustration and misery, all the pieces of Office 365 have to be in sync. The best way to ensure that is to put one person in charge of the entire Office 365 migration project. This person will need to have a good understanding of the Office 365 suite and how they interact so they can coordinate each group’s activities.

They will also need authority over the groups that manage the Office 365 components. It doesn’t do any good if each group can just ignore the Office 365 project leader. Finally, this person must have the support of both IT and business leadership in the company. As with any time you have a large group of people working together there will be differing goals. The person orchestrating it all has to be sure that leadership has their back as they make the hard decisions.  

The importance of this role can’t be overstated. I’ve been part of more than one migration that was unnecessarily painful because there wasn’t a person with the entire vision leading all of the groups. If the SharePoint team gets ahead of the Exchange team people can lose alerts or other email based collaboration can malfunction. If the Exchange or SharePoint teams get ahead of the Identity team necessary user properties may not be synced to the cloud and user based features may not work as expected. A strong leader can keep everything in sync and increase the chances that users don’t riot in the streets.  

It’s a bit tangential, but this person also needs to ensure that the entire IT team gets the training they need. If the company is migrating from SharePoint Server the change to Office 365 is big, and the IT group will need to be educated on the differences between on-prem environments and cloud technologies and strategies. If the company is migrating from something like file shares the change is huge and the IT department will need a lot of education if they’re going to be able to manage the new environment in a way that is beneficial to the company and the users. They are necessary for a solid foundation going into Office 365 and they need education to be that foundation.  

Define the entire Identity Posture: Azure AD and Exchange

After someone is put in charge of the migration process, the next step of the SharePoint Online migration is oddly enough not SharePoint. Before the SharePoint boots can get on the ground the supporting cast has to be in place. For most environments this means at least Azure AD and Exchange, and in an increasing number of cases you can throw Teams in here too. The entire Identity posture has to be defined and mostly implanted before you can think about putting content in SharePoint and expect people to be able to access it consistently. This means deciding if you’re going to sync with Azure AD, what kind of security measures you’re going to employ, etc.

After Identity is worked out, the Exchange environment needs to be solid. If the organization is migrating from on-prem Exchange to Exchange Online, that will need to be complete, or near complete before people start using SharePoint in any meaningful way. SharePoint and Exchange aren’t quite chocolate and peanut butter, but they do work together tightly. SharePoint uses Exchange for many important functions and having that relationship be in flux makes the SharePoint migration and testing a lot harder.

If Teams is going to be part of your roll-out, and it probably will be, you’ll need to have all of that defined and configured. Identity, Exchange, Teams, and SharePoint all have their hands in Office 365 Groups, so they need to be in lockstep or things get unpredictable. If the SharePoint migration is steaming along it’s tempting to keep going even if the Identity, Teams, or Exchange teams are behind schedule. Resist those temptations. Take that time to check and double-check plans. Do some more training or testing. But let the other teams get their houses in order first. 

Make an inventory of what you’re migrating

While you’re waiting for the Identity, Exchange, and Teams folks to get things into focus, take an inventory of what you’re migrating to SharePoint Online. This is probably content from a variety of sources like on-prem SharePoint, file shares, personal drives, and a whole host of other locations. Figure out what all those locations are before you move a single Word document into your shiny new environment. Have a plan for what content is going into SharePoint and in what order it’s going in.

An Office 365 migration tool like SPDocKit is a great way to see what’s in SharePoint, who is responsible for it, and how much space it’s taking up. Another one of my most commonly uttered phrases during the Office 365 migration plan is, “Don’t upgrade crap.” Not all content on-prem is worthy of the effort of migration or the space it will take up. Take this opportunity to do some house cleaning. Prune out old content, duplicate content, or content that just doesn’t fit into SharePoint Online. The more content you can prune out of your migration, the faster it will go. Crap can also come in the form of on-prem SharePoint functionality.

If you’ve installed any solutions into your SharePoint Server farm, evaluate them and see if they’re needed. If not, don’t migrate them online. If you’re not going to use it on day 1, don’t install it or turn it on. Take advantage of the flexibility of the cloud and turn functionality on later when you’re ready to use it.  

Train your Office 365 users

Earlier I mentioned the importance of getting Office 365 training for your IT Department. It’s equally important to get quality training for your user base, especially if you’re migrating from an environment that isn’t SharePoint on-prem. There should be something akin to “Office 365 101” training for your end users that helps orient them to working in Office 365. It should explain what Office 365 is, the many ways they can access it, and what some of the most important destinations are. It should also cover how they’ll work with documents, so they know how to create new documents as well as how to find content that’s been migrated.

This training should be held often and you should wait until they can get into Office 365 so they can start putting all their new skills to good use. Also consider having specialized training for advanced users like site collection administrators. This will cover topics like securing their site and taking advantage of SharePoint functionality like workflows, content types, and labels. The more you empower your users and administrators, the more likely it will be that they embrace SharePoint Online and make the most of it.                        

Have a migration test plan and team in place

While you’re planning what content you’re going to migrate, start planning how you’re going to test that it got into SharePoint successfully. You’ll also need to test the new Office 365 functionality that you’re going to use like Groups, Teams, labels, Flow or anything else. Testing itself is an onerous task and the IT department doesn’t have the time, or honestly the skill, to do it all. If your IT department is like most I’ve dealt with, IT is great at IT, but terrible at using the product. That’s where your users, especially your power users, come in to save the day. Have the content owners from each of your business units help test their newly migrated content and functionality.

Getting them involved has many benefits. It not only eases the burden on IT, but it also gives a wider breadth of testing that exposes IT to more considerations when planning. Another significant benefit of involving your user base in testing is that it gives them a sense of ownership in the migration in the new environment. This improves IT and user relations and it also gives SharePoint some cheerleaders out in the field. Change isn’t bad, but it can be painful. Having someone sitting in the desk next to them can be a calming force when a new Office 365 user is having problems.  

Migrate the content to Office 365

Of course, no Office 365 migration checklist is complete without the actual migration. This is where all of the planning, all of the best practices, all of that testing, all of that arguing about who gets migrated first finally comes to fruition. Expect this part to take longer than you expected, but hopefully more smoothly. Depending on where you’re migrating from and what method you’re using, you may be able to speed things up by spreading the load across multiple machines.

While Office 365 does do some amount of throttling, in my experience the first bottleneck is the machine uploading content to the cloud. Having migrations running from multiple desktops is the easiest way to speed things up. Also keep that in mind if you need to license any Office 365 migration tools. It might be worth the extra cost to license more workstations if it cuts down on the migration time.  

Have a plan for success: Verification and cleanup

As you’re migrating content, and once the migration is over, have a plan for what success looks like. Be able to verify it all went well. This plan will look a lot like your test plan from earlier and will also involve the business units whose content you’re migrating. This plan will also include the additional step of closing down sources once all of the content has been migrated from there. 

This might take the form of making file shares or SharePoint sites read only for a period of time, then removing the share or site collection for a while, and then finally deleting the content. You’ll need to map this all out with the content owners before the migration starts. Nobody likes surprises when it comes to content going away, and losing content will leave the new SharePoint Online roll-up with a bad first impression. 

Migrating to Office 365 and SharePoint Online may seem like a daunting task when you look at it, but once you break it down into consumable chunks it’s not that bad. While I find the non-technical parts excruciating and boring, they do pay dividends when done correctly. They help keep you and your team focused during the migration, and they give you a good road-map to follow so the whole company can appreciate all the hard work you’re doing.