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Expert Roundtable: Trials and Tribulations of Office 365 Tenant Migrations

Oct 30, 2020 by Chris Cahill

Tony Redmond, Gary Bent, Paul Robichaux, and Mike Weaver debate the issues surrounding Office 365 tenant migrations

There’s no denying Office 365 tenant to tenant migrations are incredibly challenging.

With so much data to move across multiple workloads, and pressure to ensure business continuity with a seamless end-user experience, you need expert planning and execution.

As such, we gathered four tenant migration masters for a roundtable event. Joining Quadrotech’s Paul Robichaux and Mike Weaver were Tony Redmond (Lead Author of Office 365 for IT Pros), and Gary Bent (Global Infrastructure Architect at Omnicom Group).

Gary is currently leading the world’s largest tenant consolidation project, merging 137 individual tenants into a single service, so he has a wealth of real-world experience, as does the rest of the panel.

You can stream the roundtable recording here:

O365 Tenant Migration Advice

Tony Redmond

Tony opened the discussion with his three key pieces of advice. Firstly, you shouldn’t expect to automate everything; an Office 365 to Office 365 migration tool will be able to move your data, but that’s just one part of the picture.

There are numerous Legal and HR considerations to address in mergers, acquisitions, and divestitures, and you need to deal with the human aspect of change management in addition to technological concerns.

Tony Redmond on O365 tenant migrations

Secondly, once you’ve migrated lots of raw data to the target tenant, you have to figure out how you’re going to make it as usable as possible for your end-users. The interconnectedness of applications makes this a challenge.

Finally, it’s essential to plan and test everything before execution.

Gary Bent

Gary provided tons of practical advice, particularly for large tenant consolidation projects. Ultimately, he advocates the importance of discovery, planning, and a systematic program to pull everything together.

It’s crucial to fully understand what your environment looks like, and only then can you get executive buy-in at the corporate level. You need to outline the benefits of the program you’re undertaking and showcase your strategy, and the upfront discovery is key to success here.

It’s essential to clearly articulate your mission statement to get buy-in from the very top. If you’re merging 137 different tenants, incorporating thousands of brands, agencies, and staff, if you can’t get buy-in from the top, how can you expect to get buy-in from everyone else?

Gary Bent's tenant migration advice

Tenant consolidation at this scale isn’t really about migration – it’s organizational transformation.

You need thorough planning, taking a ‘T-shirt size model’ approach to figure out your small, medium, and large tenants in order of complexity; not simply size in terms of users and mailboxes, but how difficult each tenant is going to be in terms of interdependencies that need to be considered.

As Gary concluded, you can’t take care of everything line-by-line; tenant consolidation is really a mini-M&A activity every single migration weekend, and you have to track progress efficiently, both the things are going as expected as well as all the unknowns that come up.

It’s a case of continuous improvement rather than delayed perfection, and you have to be prepared to crawl, walk, and run before you sprint toward the end.

Paul Robichaux

Paul stated the importance of communication to end-users – before, during, and once complete. You almost can’t over-communicate; everyone needs to know what’s happening – and when – to avoid any nasty surprises.

It’s important to identify at least one, and preferably several, pilot groups you can work with during the migration to finetune your communication and make sure you understand all the impacts of identity, mail-routing, etc. because you don’t want to have planned your migration, and start it only to find something doesn’t work.

Agree on a set of small goals, test them, verify that you hit them, and then set bigger goals – progressively and repetitively.

Paul Robichaux on Office 365 tenant migrations

You need to prepare your service desk to maintain First Call Resolution. If 99% of your data migrates perfectly but you have 10,000 users, that means you’re going to have 100 panicked employees when they discover something’s broken on Monday.

You have to be ready for this surge, and ensure your service desk team has appropriate training to resolve issues.

Additionally, you have to know where the seams are, i.e don’t plan a migration for your busiest time of year as the risk of disruption becomes all too great.

You should also have a backup plan should things go wrong, whether that’s to cut back over to the original tenant or to have a SWAT team of migration engineers on hand.

For example, we had an issue with one of Gary’s tenants, and normally Microsoft has to eject the domain so you can re-home it, but that didn’t happen. Microsoft had a long delay, but we had a backup plan ready for interruptions to timelines.

Mike Weaver

Mike referenced his experience in overseeing numerous Office 365 tenant migration projects at Quadrotech.

His initial piece of advice is to focus your time, collecting data to understand what’s being used and what to focus on. You want to know: What’s enabled? What are the data volumes?  and What’s the activity?

Mike Weaver on Office 365 tenant migration advice

The final point is the most important one; if there are areas of low data volume but high activity, you need to focus on the user experience to ensure you can handle the first few days in the new tenancy.

For example, if Yammer is enabled for everybody on a tenancy, some organizations would focus on how to handle this migration as there are limitations with the API. However, if you were to track the usage via Office 365 reporting software, you might find only 50 users out of 3,000 are actually using it, so the problem is better solved by informing those individuals they’ll have to recreate on the other side.

By taking this approach, you can simplify your project and focus on the items that really need your attention, such as identity management, domain issues, and SharePoint applications.

You need to make data-driven decisions and collect as much information as possible about the source tenant and its configuration so that you can have a successful project.

Final Thoughts

Our expert panel answered several questions, both during and after the event, which you can find in our Tenant Migration Q&A Roundup.

The overarching sentiment from the event was that these projects are extremely complicated, but if you follow the mantra of ‘Plan, Move, Manage’ you’ll set yourself up for success.

If you have an upcoming Office 365 tenant migration and would like to discuss your project with our specialist team, please contact us. Having moved petabytes of data between tenants for international organizations like Omnicom, our migration experts are ready to help.