Part 4: What the Business Should Think About When Migrating to SharePoint 2019

Migrating SharePoint 2019

Part 4: What the Business Should Think About When Migrating to SharePoint 2019

By Tracy van der Schyff | May 02, 2018

In the previous blogs of the series we looked at the start of SharePoint, how the tool evolved over the years, and what we can expect from SharePoint 2019. Check out the earlier blogs here:

Today in part four of the series, I’ll share my considerations for migrating to SharePoint 2019. Migration is never easy, but it helps to be informed. Let’s look at what needs to be considered, some tips on cleaning up your data and bringing OneDrive for Business and Microsoft Teams into the loop.

I mentioned Microsoft Teams, as more and more companies are considering Hybrid environments to leverage both SharePoint Server on premises and Office 365 SharePoint Online to achieve their business goals.

As the Migration methods support to SharePoint 2019 has not yet been announced this article will focus on the ‘generic’ considerations when migrating. As I believe that business should be more involved in the Migration process, I will focus more on the considerations from the end user / business perspective. Many resources provide the technical checklists and migration tools such as Content Matrix which will help you remove the complexity from your migration.

According to Adam Levithan, the 3 Steps for Successful SharePoint Migration comes down to:

  • Analysis
  • Planning
  • Optimizing

We know that successful projects require at least 80% planning and 20% doing, still we rush into these and the results are self-explanatory. By following the correct Project and Change Management Methodologies we already decrease challenges and increase the likelihood of success. Through this I’m trying to say: “Don’t rush into it, take your time and make the right decisions for your business. A migration is the perfect time to improve.”

SharePoint 2019

I’ve been using SharePoint Online for a couple of years now, and of course the integration with the other Office 365 Apps and Services makes it the ideal business environment. However, when I have clients who need to stay on-premises due to data compliance or cost, I suggest they upgrade and migrate to SharePoint 2019. SharePoint 2019 might still be on-premises, but this version will bring us even closer to the SharePoint Online version. Expectations are modern UX, Flow & PowerApps integration and of course Next-Gen Sync Client Support. I’m hoping for a lot more, but we’ll have to wait and see.

Transform your business

Companies upgrade to new versions for the added benefit of new functionality and the technology that sits behind it. Surely if we want to leverage the latest technology, we also need to ‘upgrade our way of thinking’. In my eyes this is one of the greatest risks in migration projects. “Lift and Shift” migrations simply replace what we have, on a more expensive platform.

Technology alone does not transform business and often a redesign of processes and architecture is required to truly take a company to the next level. If you are considering migrating to SharePoint 2019, now is the time to take a step back and look at the bigger picture.

In my analogy I’d like to compare a physical address book with a contacts app on my smart phone. Simply migrating the information from one platform to another will make no sense, as the newer technology deals with the contacts (database) in a different way.

On SharePoint, for example, you might have libraries with Excel spreadsheets or Word documents with the contact information of employees, now might be the time to consider doing things different. Especially with the future integration of Flow and PowerApps, the possibilities are endless.

physical address book

The environments you migrate from will affect the methods you use and decision you need to make. No business environment is the same and based on your industry, your business-critical apps will be different.

SharePoint (OneDrive) to SharePoint (OneDrive) Migration

If your company and users have already adopted SharePoint and OneDrive, then this would be the least disruptive migration. Apart from the usual complexities of which customizations is at the top of the list, you would benefit from migration tools to move your content from one environment to another.

It would still be necessary to make decisions about which content should be migrated or if all solutions are to be brought over.

File Share / Other Cloud Storage to SharePoint (OneDrive) Migration

File Share migrations always prove to be a challenge, and not because of the technical ability to migrate the content. The “information architecture” designed through years of creating nested folders should be completely redesigned to fully leverage the latest features and functionality offered by SharePoint.

Moving these environments as is (lift and shift), is not something I would suggest and as painful as it might be to redesign and make decisions about content, it will be worth it in the end.

Hybrid – SharePoint 2019 / SharePoint Online

The Hybrid environment has much more to offer, and based on this, also more considerations. For example:  migrating from an existing SharePoint on-premises mix OneDrive / File Share environment to hybrid opens many opportunities to move the content to platforms better suited, which also offers better collaboration capabilities.

The previous Human Resources department would benefit by being moved into a Microsoft Team (with a SharePoint Site Collection in the background). Business critical data might move to SharePoint 2019 on-premises (data compliance) and your Intranet could move to SharePoint Online to utilize the new Communication Sites, Hub Sites and News capabilities. File Shares on the other hand would move to a combination of SharePoint, Teams & OneDrive based on the target audience of the content.

SharePoint, Teams & OneDrive based target audience

Basic Considerations

  • Given the above examples, you’ll see why it’s important to use the opportunity to not only move your content from one environment to another, but also improve business process.
  • The new environment might have improvements or features not previously possible in your current versions. This will also affect your decisions around where content should go, to name a few:
  • Large file support (10Gb)
  • External Sharing
  • (Less) limitations on characters in file and folder names
  • URL Path Lengths (256 increased to 400)
  • Archiving content should be considered and based on your industry you might only need the last 5 years in your new environment. An alternative could be to only migrate the last financial year, and to migrate previous financial years to a different type of storage, which is still searchable through SharePoint.
  • You need to consider Site collections vs Subsites as the industry has moved towards ‘flatter site structures’.
  • For Hybrid you need to need to align your decisions around what goes into the Cloud and what stays On-premises to your compliance needs and regulations.
  • Garbage in, garbage out should drive your decisions on migration of disorganized data – it’s simply not worth it.
  • Complex permissions as found in File Shares should be handled with care. Ensure that the product you use for migrations takes care of permissions.
  • Run checks for duplicates, there will be thousands of duplicates which does not have to be migrated.
  • Identify owners of data and involve them in the pre-migration checks, audits and testing.
  • Classification of data in the new system will be of great value to the business, consider this as part of your clean-up project.
  • The Migration Duration will be reliant on the volume of data, network and system speed. Test this beforehand and adjust your plans accordingly.
  • As with any project, Change Management must be included. Without sufficient communication and training your project is sure to fail.


Migration might seem like an impossible task, but keep in mind that it’s part of a bigger project, and that is to improve your business. Migration is not a strategic objective, empowering your business users and transforming your business is, migration is merely one of the actions taken to ensure this. Have an open mind to possibilities and do not limit your business growth by simply replacing what you have. Take a step back and take (more) time to consider how migration could also empower your business.


A Beginner’s Guide to Planning a SharePoint Migration

Plan Your Content Migration

Microsoft is Giving Away OneDrive for Free: Should You Switch?

Top 5 Roadblocks When Migrating to the Cloud

SharePoint Migration Clean-up and Pre-Migration Checklist for Success

Office 365 & SharePoint Migration Solutions

Content Matrix

3 Steps for a Successful SharePoint Migration

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Tracy van der Schyff

Tracy is a Microsoft MVP and an energetic, hyperactive adrenaline junkie who sees challenges and issues as opportunities and thrives on improving processes, environments and the general quality of life. Her broad knowledge about IT and Business gives her the ability to communicate on both levels and convey meaningful requirements and narrow the (ever present) gap between the two.

Written By: Tracy van der Schyff