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Best Practices for a Smooth Office 365 Migration

By WatServ
February 11, 2020

So, you want to migrate to Office 365?

There are so many reasons why an organization would choose to migrate to the cloud. The most common reasons are based on some sort of organizational deficiency, such as communication, collaboration, business application performance, personal productivity, store/find/share data and mobility.

So, your decision is made and now you need to put all this new technology in front of your workforce and expect them to like it… because you care about them and it’s going to make their work life better! Well, getting from point A to point Z will most certainly disrupt their daily routine and cause angst among the masses. Here are some ideas on how to avoid the pitfalls of implementing Microsoft Office 365 and how to prepare your deployment team and end-users for the proverbial road ahead.

Choosing the Right Licensing Option!

This one is tricky. Only because as of July 2018, there are roughly 640 different licensing options to chose from! In all fairness, the total includes the different pricing for the Business, Government, Nonprofit, and Education SKU’s (Stock Keeping Unit), which multiplies each SKU by four. Each one has its own pricing model and discounts. The total also includes Dynamics 365, Office 365, Microsoft 365 and all the add-ons that are currently available with the online environment. There are about 280 available for Office 365 specifically. As you can imagine, it can be quite daunting to determine which SKU best fits your end-users.

I would suggest getting an overall snapshot of the different work-groups in your organization – Sales, IT, HR, Finance, Marketing, Operations, Production, etc. Once you’ve identified the different work-groups, you’ll need to break down the various work functions within each of those groups. Most users will need a license that includes Office 365 ProPlus to perform their work duties, but there may be some that don’t. For instance, does a temporary employee need Skype for Business or SharePoint if they’re just going to be doing spreadsheet work on a 6-month accounting project? Does a line worker in the plant need Outlook or can they get by with Outlook Online? Then there’s the add-in SKU’s to think about. You’ll need to determine who will need Project Pro, Visio Pro, Power BI Pro, and so on. There’s a lot that needs to go into figuring out the license pool.

Prepare Your Environment!

I think this is one of the most difficult tasks to complete prior to the migration, but quite possibly the most important task you can do to help the migration go swimmingly. This is true for small migrations too. You can never do enough pre-planning!

The types of issues that can pop-up due to lack of planning are plentiful. For instance, you need to make sure your on-premise Exchange server is running the correct version of Exchange depending on the type of migration you’re planning – Cut-Over, Staged or Hybrid. Here, you’ll need to spend some time cleaning up your local Active Directory to ensure you’re only bringing over the data/users you need and not all the lingering stuff you’ve been meaning to cleanup but haven’t dedicated the time to get rid of it. Now is the time to get that done! Likewise, if you’re planning on migrating a file share out to SharePoint, you’ll need to spend some time cleaning up the data and architecting the new folder structure, security access to the various Team Sites and overall access to the data by the end-users.

Another SharePoint gotcha is the proper migration of the meta-data associated with each file and folder. Simply copying the file is going to change the creation date, the change date, the author, the created by, etc., etc., etc.

One item that is overlooked, more often than not, are all the systems that rely on the Exchange server functionality. You think you’ve identified them all, but there’s always that old relic legacy system in finance that pops up and you get a call that says, “We have a problem!”. Some to look for are auto-invoicing customers from an ERP system, emails from alert systems, conference rooms and equipment, KPI reporting, HR connection to the AD, etc. Make sure to document and thoroughly test all systems that are integrated with your Exchange server prior to beginning the migration!

Microsoft provides a really good tool to help you determine if your environment is ready to go. Check out this Microsoft TechNet – Prepare for setup with health, readiness and connectivity checks.

Selecting the Right Team!

Without a doubt, the number one factor to ensure a successful Office 365 deployment is the team that’s going to support the decision to implement Office 365, deploy it, use it and support it! Without a committed project sponsor, a talented project manager, a smart migration team and a responsive training and support team, you’re doomed to fail. Choose wisely!

  • The Executive Sponsor(s) – the more the merrier! – The more top-level supporters within your organization that you can rely on when issues present themselves the better off you’ll be in the long run. More than one will not only make your life easier but, it will increase the user adoption rate and help with the business unit commitments across the organization.
  • Project Manager and Migration Team – These two groups will be working together throughout the migration project. The PM’s will be there to keep the project on task and minimize the chaos that will most definitely ensue. The migration team will be heads down making sure the migration batches are performing error free, all the scripts are running as expected, the Azure Active Directory (AAD) is fine and many, many other tasks simultaneously. These two groups will have their thumbs on the pulse of the project. They’ll know everything about everything – or close!
  • Champions – This is very important as these will be your frontline supporters. These are the individuals that are respected among their peers within their business units. These are the folks you’ll rely on to disseminate key project information and act as a buffer between your migration team and the end users. You’ll get to appreciate (and feel sorry for them) as you go through the deployment. Communication is key to a successful rollout and the Champions can help spread the word. Make sure the communications are short and concise. The last thing you want to do is spam out paragraphs and paragraphs of information that your users will not read. Think Twitter – you’ll probably need more than 280 characters to get your point across, but you know what I’m getting at.
  • Training and Support – I can never emphasize enough how important IT training is to everyone in your organization. It’s the core of how works gets done these days. So, it’s imperative that your user base understand, as much as possible, how the environment works. Not all users will accept innovation the exact same way or at the same pace. Your training group should understand that and create fun and interesting training modules that your organization can learn and have some fun at the same time. The approximate breakdown of users in a typical organization are Innovators (2.5%), Early Adopters (13.5%), Early Majority (34%), Late Majority (16%) and Laggards (16%). You should initially focus on the top 3 and the rest will follow eventually. The more training options you provide, the better your support team will be able to support your organization.

Another good source of information regarding success scenarios are on Microsoft’s FastTrack Center site –

Reference the “Microsoft Office 365 Adoption Guide” for more information regarding team selection and understand the various team members needed to be successful.

Select your Migration Strategy!

There’s a lot that will determine the appropriate migration option for your organization. The two biggest considerations are the Exchange server version and the number of users you’ll be deploying. If you have an Exchange 2013 server and less than 150-200 users, a cutover migration would probably work fine. A Staged migration can be used if you only want to migrate a batch of users, groups, offices or locations over at a time. Staged migration has Exchange versioning limitations too and should be used for a 200+ users or more. If you wanted to keep your on-prem Exchange server, but sync it with Office 365 in the cloud, then a Hybrid migration would be used. There are plenty more gotcha’s when trying to determine which option makes sense.

Cutover Migration

The most common migration used when moving your organization to Office 365 is the cutover migration. It’s the most straightforward and less complicated of the 3 options – Cutover, Staged and Hybrid. A Cutover migration is just like the name implies, you cutover every user to the new Office 365 tenant at the same time. One day they’re accessing their mailboxes on the old on-prem server, the next they’re accessing the new tenant. It requires everyone to be ready and to make the necessary changes all at once. It can get quite chaotic making everyone switch together.

Staged Migration

The Staged migration is ideal for bulk migrations selecting a group of individuals that will be migrated at specific time intervals. This type of migration is somewhat more complex as it requires your local Active Directory (AD) to be synced with the Office 365 Azure Active Directory (AAD) using Azure AD Connect. The two AD’s will coexist throughout the completion of the Staged migration. Once the last batch of users have been migrated, the on-prem Exchange server can be decommissioned and the Azure AD Connect can be uninstalled. The new Office 365 tenant can be managed using the AAD through the Admin portal online.

Hybrid Migration

The Hybrid migration is similar to the Staged migration because it too requires that the on-prem AD and the Office 365 AAD be synced via the Azure AD Connect tool. The Hybrid migration is meant to allow for both on-prem Exchange activity for a subset of your user base as well as options to place another set of users out on the Office 365 tenant. It’s a coexistence configuration where you can manage both on-prem Exchange servers and Exchange Online simultaneously.

How to Measure Success!

User Adoption is key. You can determine a successful implementation by measuring the adoption rate (Mailbox, Teams and SharePoint usage, Skype for Business IMs and conferences and minutes of Skype for Business). All of these reports are easily generated using the Office 365 Reporting site.

  • Training effectiveness – You should determine a baseline of your user’s knowledge on using the Microsoft Suite of products. Then after your deployment, you can generate reports using the O365 Reporting tool to compare pre and post migration rates. It’s also a good idea to continue providing the adoption metrics to the project sponsor and champions to determine the effectiveness of training and to determine where your training focus needs to be directed for various user groups. You should also build an FAQ database on Yammer to put basic questions like, “Where to start a conversation – Yammer, Skype for Business, Teams or Outlook?” “Where should I store a file – Teams, SharePoint or OneDrive?” And constantly promote the FAQ so new employees know where to go to find help.
  • Reduced operating costs – This information is key to the Executive Sponsor because everyone wants to know they’ve made the best possible decision to save the company some money – especially when it’s costing the company initially. You can combine the user adoption reports with the financial/accounting reports, Help Desk reports and travel expenses to get an idea of how Office 365 has affected your organization financially.
  • Increase productivity – This one is a hard metric to determine and even harder to present in a meaningful fashion. The increased adoption correlates to faster communication internally and externally, faster decision making and shorter time to complete certain tasks like customer order processing, automated invoicing, proposal generation. The goal is to provide metrics that show an increase in productivity and a decrease in time to complete tasks month over month.

Once you’ve let the dust settle from the deployment, it’s always a good idea to consistently check in on your workforce. I mean after all, you have just disrupted a major part of their work environment (for the better of course, they just don’t know it yet!). You can conduct end user surveys using Yammer groups and discussions to get immediate feedback to determine employee satisfaction. And, you get users using all the new technology that’s available to them with an Office 365 subscription.

Reference the “Microsoft Office 365 Adoption Guide” for more information regarding success measurement.

So that’s it in a nutshell! This isn’t meant to be a complete, in-depth guide to performing a migration in your organization. There’s plenty of geeky migration materials provided by Microsoft to accomplish what you’re looking to do. There are no shortcuts to managing a complex migration, but there is help if you need it. Let us know if we can be of assistance to your organization.

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WatServ is an IT solutions provider that helps clients digitally transform their business through cloud technologies and services. Founded in 2006, WatServ specializes in providing hybrid and multi-cloud solutions and hosting complex, high-availability environments for enterprise-level applications. WatServ’s unique approach to planning, migrating and managing multi-cloud environments, plus premium 24x7x365 support, enables its global customers to focus on their core business. Relying on Microsoft and Google’s public clouds, in addition to its own private cloud, the company offers an ideal managed cloud environment engineered for security, reliability and performance. With offices in Canada and the United States, and with 1000’s of users connecting from around the world, WatServ is always on. For more information, please visit

WatServ is an affiliate of Brookfield Business Partners (BBU), a public company with majority ownership by Brookfield Asset Management Inc. and listed on the New York and Toronto Stock Exchange. More information about BBU is available at

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