Microsoft 365 tenant-to-tenant migrations: AI trends, migration challenges, and IT strategies  

How can you make the best out of a Microsoft tenant-to-tenant migration? Microsoft MVP Richard Harbridge discusses how to use your migration project to reshape your approach to modernization. 

Tenant-to-tenant migrations are commonplace in today’s fast-paced IT landscape. For IT professionals, technology’s exponential growth brings more challenges to this already complex process, from managing data sprawl to ensuring security and compliance and addressing learning and adoption.  

During his ShareGate fireside chat, Microsoft MVP Richard Harbridge discussed Microsoft 365 tenant-to-tenant migrations, covering key considerations such as the growing role of AI and user adoption strategies. 

In this bonus recap article, we share the highlights we couldn’t fit in from our discussion. Richard talked about trends and challenges and what advice he can share to navigate the complex tenant-to-tenant migration process effectively.  

Watch the fireside chat recording and check out our bonus recap below for the cut scenes! 

Managing sprawl

The accelerated growth post-pandemic led to increased data creation. ‘Sprawl,’ as we know it, occupies unnecessary space in almost every organization’s cloud environment and translates into greater risk, including: 

• Security: Security risks grow as data becomes more and more unmanageable. If you’re not in control of data in your environment, it means your monitoring capabilities are limited, leaving you vulnerable to accidental sharing or data leakage. 

• Costs: By not removing sprawl from your workspace, you’re racking up unnecessary storage costs that might later come to haunt you.  

• Productivity decrease: With irrelevant data in your Microsoft 365 environment, users’ search functionality will be negatively impacted. Productivity will decrease as users will spend time either creating duplicate data or spending more time trying to find what they’re looking for.  

• Value destruction: If you can’t find valuable information within your Microsoft 365 environment because of sprawl, you’re missing out on leveraging that data.  

In this clip, Richard highlights big changes in managing tenants over the past year. He says it’s crucial to handle sprawl and security rules and prepare for AI’s huge growth.

AI integration 

We’re all witnessing the rise of AI. But what’s truly surprised everyone is the short timeframe we all have had to adopt this new way of work. Just consider how, within Microsoft 365, we now have these AI-powered tools like Copilot. Early adopters vs. those who ignore what’s at their doorstep is something every IT professional should consider.  
 

So, how should we think about AI integration into the modern workplace? Richard pointed out some key aspects: 

From digital assistance to organizational workflows

According to Richard, the exponential growth of AI into organizational workflows means starting with training AI with your organizational data. The more organizational data availability your AI has, the better the data quality.  

And this directly impacts productivity gains within your company. If the AI accesses the right data, your team can benefit from more than 100% productivity gains. This will be powered by functional agents. Where teams previously used AI for digital assistance, we’ll have AI-powered functional agents (like Copilot) that can do things on your behalf.  

With these functional agents, we’ll achieve more because we don’t necessarily have to supervise task execution at every small step. The functional agents will be capable of doing this very effectively on our behalf. This transition to functional agents generally means a better ROI. 

In this clip, Richard highlights the need for IT professionals adopting AI to prioritize data security, compliance, and technical debt while leveraging AI to enhance communication, simplify cloud management, and optimize operations.

Maximizing ROI

Of course, like everything else, AI integration should be an ROI opportunity for the company. But where do you start? Richard says the process should be gradual.

Companies shouldn’t be too quick to try and get an ROI out of things like AI-powered functional agents. The priority should be ensuring people can maximize the value of these tools.  
 
This means explaining to people how to use AI in their everyday work. Train them so the foundation is set right. Once they’re equipped to use functional agents like Copilot properly, you’ll see higher productivity gains and, generally, maximization of your ROI on AI.  

Migration challenges and strategies 

We get it. Migrations are tough. And such projects can quickly spiral out of control if not handled carefully.

While the number of on-prem to cloud migrations might be shrinking, we have new migration challenges like a growing SaaS (software-as-a-service) landscape, dealing with multi-tenant environments, and moving everything with mailbox migrations.

Here are some key points and insights from our discussion with Richard:

1. Growing SaaS landscape 

The number of SaaS apps organizations use today is only growing. Richard points out that the average number of SaaS applications in teams of less than 50 people is around 16 SaaS apps, while the number grows with larger organizations to more than 160 on average. And while companies are looking to consolidate, it’s still a complex process of moving everything to a new tenant when a migration project pops up.  

2. Multi-tenant environments 

Many organizations today are multi-tenant environments, and this trend continues to grow. The reasons might vary, but it’s an inevitable reality that IT teams face during migration projects.  

Of course, the challenge is moving all the unique data, settings, preferences, etc., that come with each unique tenant. While Microsoft is working towards making single tenants more multi-org supported, the challenge is dealing with all these information barriers at present.  

3. User preferences in the context of a mailbox migration 

People care a lot about their workspaces and what gets moved during a migration.  

For example, when ShareGate launched mailbox migration, it was initially in public preview. During this time, we were still refining the feature, with plans to add more features upon general availability. One of these features was mailbox rules. Now, you might wonder how important mailbox rules really are. Well, they turned out to be quite significant. Some of our clients expressed that while they were pleased ShareGate supported mailbox migration to some extent, they couldn’t fully use it until their users’ mailbox rules were transferred over. 

Strategies for modern Microsoft 365 migrations 

How do IT teams respond to this while keeping migrations hassle-free? Richard recommends the following: 

1. Improving employee experience through continuous learning and adoption is one way to bridge the gap. It’ll be easier for everyone to adjust once they know what to expect after migration. For example, when a tenant-to-tenant migration happens in the context of a merger and acquisition, one set of employees will probably be more tech-savvy than their counterparts. But, if you can find a way to train everyone so they know what to do post-migration, it’ll be easier for everyone to adjust. 
2. Separate migration and optimization projects. This is a common mistake organizations make. Restructuring or optimization projects normally never end. But with migrations, a project should have a clear end date. So, make a clear distinction between when you need to restructure internally or when you need to move things.  

Change management and user adoption 

Change management in our context means ensuring you have the right strategy to drive user adoption post-migration. There will be internal resistance. You might give people all of these new AI tools, but it will take time for employees to use them. The transition to the new way of work means showing people how useful these tools are.  

Richard recommends companies use AI to improve communication since that’s the easiest place to start, and Outlook is a great starting point. Tools like Teams and SharePoint come later. If you can get people to adopt AI for their meetings or email experiences, it’ll be easier for them to understand the value of this new way of work.  

Looking ahead 

Looking ahead, organizations need to embrace AI and its possibilities. With tools like Copilot in play, workplaces should set clear guidelines for using AI effectively and safely.

This means everyone needs to come together to overcome any challenges that arise. While AI can bring productivity boosts and long-term gains, we must watch out for security issues and misuse. That’s why it’s key to be proactive and have solid strategies in place.

Tenant-to-tenant migration Q&A with Richard Harbridge

Is an AD migration/integration a hard requirement before migrating tenant data (i.e. mailboxes, OneDrive, Teams, SharePoint)? 

Generally speaking, it must always be understood and planned for as there will be experience, technical, or other impacts that you may be comfortable accepting or making temporary. But, there is always a cost, and uncovering those costs and impacts sooner is always better than later.

However, the longer answer is… it depends. Technically, it isn’t a hard requirement. Some customer tenants can have cloud-only identities or other patterns at play or may have special reasons (often accelerated timelines) that encourage a model where the content and users are moved and then adjusted later (or left as ‘Azure AD/new/Cloud only identities).

The majority of cases to be clear will have the dependency as noted but there are always exceptions and alternatives. 

How can we facilitate or make the change process easier when migrating from file shares to SharePoint Online?  

File shares are tools many of us have used for decades and we are used to navigating them a certain way. You can create similar experiences with SharePoint and OneDrive features, for example:

1. You can use OneDrive Shortcuts. Instead of mapping network drives, encourage users to create shortcuts to SharePoint libraries in their OneDrive. These shortcuts are accessible across devices and offer improved performance compared to traditional mapping.
2. Alternatively, you can auto-configure SharePoint site synchronization for users. This leads to an experience that looks and feels like local drives but uses the sync engine in OneDrive/SharePoint instead.  

While there are other patterns, those are probably the top two approaches organizations use.