The top 5 considerations for migrating to Microsoft Office 365

We get the basics, but what do we really need figure out before we make the jump to Office 365? Theresa Miller digs in.

We know that Office 365 is growing quickly—Microsoft has indicated that they now have over 70,000 customers. But of course, as popular as it’s getting, most of us haven’t made the jump yet and are still watching and evaluating. Really, the main thing we know is that moving to Office 365 means relying on the cloud and getting newer versions of the desktop apps. And here on BrianMadden.com, Gabe and Brian have written about how hosted Exchange can affect desktop virtualization. (Update: They’ve also written about some potential solutions, too.) But that’s just scratching the surface—what else do we really need to know? That’s what I’ll look at today.

1. Security and compliance

When migrating any corporate information to the cloud, security and compliance are often the top concerns. However, when researching cloud initiatives with your security colleagues, you will find that they are often very supportive of moving to the larger cloud providers like Microsoft. The truth of the matter is that an Office 365 tenant is typically more secure than your on-premises environment.

Why and how? Well, Microsoft has put a lot of effort into ensuring the technology that holds corporate data is secured. Their infrastructure is top notch, highly available, redundant, and patched. Are all of these true of our own infrastructure? If not, then Office 365 is already more secure than your onsite deployment.

2. Cost

Some organizations immediately shutdown on the idea of Office 365 because of cost. Now, the reality of this is that there is an expense tied to moving to cloud. It’s not free, but it’s not off the charts, either. When you move to the cloud you are accepting the fact that you are paying someone else to keep your infrastructure up to date. This means that you are no longer in the business of buying servers and storage, patching, maintenance windows, cooling a datacenter, and having staff to run it all. In other words, it’s shift from your capital budget to your operating budget.

One other thing to remember in your financial strategy is that you should expect to have a period where your data is both in the cloud and you will still be maintaining your onsite infrastructure, creating some cost overlap.

3. Functionality

It’s important to consider whether or not there will be any residual effects to functionality when moving to Office 365. I will be honest here—things will be different and there will be some learning curve for users—but in general you will find that most things work very similar if you already have Microsoft products in your organization. Just plan for some user training.

That being said, there are definitely some functionality differences to considered in advance of a deployment. Here we go:

  • Do you need a seamless experience, so that your business users can still access all their information as if it was on-premises? In most cases the answer to this question is a resounding yes, so make sure you research and implement identity options such as Active Directory Federation Services or similar. Having a plan to provide the single sign on experience your users expect is fundamental to the success of your project.
  • Test and then pilot the areas of Office 365 you expect to deploy to your organization. Their feedback will drive the success or failure of this project. IT departments today deploy what the business needs, and not whatever they want. In my experience, proper testing is necessary or your project will fail.
  • Know that with Office 365 there are layers of redundancy of data, recycle bins, version control, and retention policy, but there are not any actual backups. Before you can decide if you will be comfortable without backups, take some time to understand the inner workings of Microsoft’s options and then compare these against the recovery and uptime expectations of your organization.

4. Should we consider hosted email, too?

What about putting your email in Office 365 Exchange Online? I have been administering and deploying Microsoft Exchange since the late 90s, and while I have a deep technical connection with the on-premises product, I now also have a strong connection with Exchange Online. I feel that if your organization has a cloud strategy, then Exchange online should be part of that conversation, too.

5. Does this affect your job?

I find this topic extremely interesting since it impacts how we function as an IT department as well as the work we do from day to day. Does cloud really have the potential to take away our jobs in IT? First, the reality is that we are a long way off from any organization moving to all cloud, and there is still much to learn and do should we actually get there. Keep in mind that as we shift to a cloud strategy it means that technical staff has the time and opportunity to expand their wings and learn other types of technology.

Even in the event that someday we see all organizations achieving an all cloud strategy, there is still work to be done—consider cloud to cloud migrations, for example. Also remember that IT supports the business, and that businesses runs on technology. We will always be there to help them. 

Final note: It’s not scary!

Don’t be intimidated by Office 365 just because it’s in the cloud. Just like any other technology implementation, a move to cloud requires business acceptance, training, design and implementation.

If there is one thing I have learned over the years, it’s that technology is always advancing and in this field we are always learning. So bring on the change, and look forward to how you can advance your organization’s IT strategy, and to what you get to learn about next!

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I am impressed! 70,000 customers! Whow!! Who are you trying to kid or convince! The product is too complicated, to full of errors, to many big mistakes and basically a missed oportunity for MS to break into this market a few years after every one else. Admit the issues you have and come up with a product that really amaze! For MS, thar was a long time ago
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The only reason Microsoft has 70,000 customers licensed for Office 365 is because of enterprise agreement renewals forcing customers to go cloud. I agree with the other poster office 365 is as buggy as Windows 95.
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Baretull and BOSCOIRL - Could you give specific examples? Any more details you can give would be quite helpful.
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My biggest issue with O365 is pertaining to Hosted Apps and VDI and the suggestion of caching OST and OneDrive files back to our DC's. I presented at our local CUGC I think O365 is like the "Iceberg" to our "Titanic" Hosted Apps and VDI solutions". Seems like a minor disruption on the surface but the underlying technology and deployment methods have the potential to sink our investment in centralized Hosted App and VDI solutions.

Putting all of your home drive data and mail in the cloud and then having to cache it back to your data center to a VDIHosted App to redirected storage either via UNC, VHD or other solution to mask performance issues is not a great idea and up until 4-5 years ago it was not a recommended or supported solution. 

I actually just posted a suggestion to MS to get an officially supported Hybrid approach where people can use a mix of OWA and OneDrive web with thick office clients to create a great UX while still getting the benefit of O365 on a hosted solution and eliminate the cache insanity.
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Hi Paul - Have you checked out FSLogix? Gabe has written about this before:  http://www.brianmadden.com/opinion/A-preview-of-FSLogix-Office-Containers-and-how-you-can-finally-redirect-OST-files

(When we contracted with Theresa for the post, I asked her to concentrate on other aspects since we already had Gabe’s article. I added a link to the post to make it more clear.)
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Fslogix were my CUGC sponsor and co-presenter. I get the technology and I really like it but they are just making a bad design idea work a lot better. The underlying problem of sending everything to the cloud and then bring it all back again in the form of a cache and keeping it on NAS, SAN or other storage in the DC just doesn't make sense on scale just so you can make your O365 decision seem like a good one. If you are caching to local cheap spinning disk on a pc or laptop not a big deal.

I think the better compromise could be a Hybrid approach of Webmail and OneDrive web mixed with the Office thick clients for Word, Excel and Powerpoint. This is how most people work at home already today webmailcloud storage and thick clients for editing. Which is my proposal for the MS O365 team to create a supported hybrid method for hosted solutions.

https://office365.uservoice.com/forums/264636-general/suggestions/18018202-hybrid-o365-2016-pro-plus-deployment-for-rds-and-v

Small and medium businesses with the majority of users leveraging office productivity apps on local devices O365 makes a ton of sense I get it 100%. Large scale businesses with large investments in centralization using Hosted Apps and VDI this has serious potential to disrupt your existing deployment and drive up your costs and complexity significantly.
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