This content is part of the Essential Guide: The essential Office 365 migration guide

Lessons learned from an Office 365 migration

Office 365 migrations take time and careful research, but even then, some mistakes are inevitable. Find out what one expert learned during his company’s move to Office 365.

Are you considering an Office 365 migration? If so, you’re probably asking the same questions my company did: Is...

it a good deal? Does it have the services we need? Is it everything it claims to be?

Well, we’re still figuring out how to wrap our business processes around Office 365’s new way of computing. But our data migration was remarkably seamless, and we are generally pleased with the service thus far.

Now that we’re one month into our Office 365 relationship, I  wanted to share what we learned with prospective users of Microsoft’s cloud-based collaboration and productivity suite:

Lesson 1: Do your homework before deciding on an Office 365 plan.
Our company is a prototypical small business, so we’re far from Office 365’s Plan P1 50-user maximum. For that reason, we were initially swayed by Plan P1’s $6 per user per month price. But after we dug into the specifics, we quickly learned that our needs extended well past P1’s capabilities. In the end, our small business found that it needed Plan E3. I’ll elaborate on this initial mistake in later.

Lesson learned: Research all parts of each Office 365 plan before selecting one.

Lesson 2: Properly prepare before starting your Office 365 trial plan.
Because Office 365 relies so heavily on Web browsers, we wanted an easy-to-type subdomain name since our users will be typing it for years to come. When we initially registered for our Plan P1 trial, we were excited to learn that our first subdomain choice was available. Unfortunately, choosing our domain name early in the process created a problem when we decided that we needed to move to Plan E3.

Once reserved for a P1 plan, a subdomain name is locked. Since we subsequently moved to Plan E3, Microsoft could not give us that subdomain without a 90-day waiting period, even though we owned it. This problem will hopefully be resolved soon.

Lesson learned: Don’t start your trial until you’ve chosen the correct plan.

Lesson 3: Time your plan purchase with your Exchange migration.
Any Office 365 plan is just a costly and empty shell until you fill it with user data. Beginning your Exchange migration immediately after starting your plan is important because it helps you avoid paying for a service you’re not using. Exchange migrations take time, so make sure your timeline is in accordance with your Office 365 move.

Lesson learned: Make sure you’re ready to migrate data to Exchange 2010 before purchasing your trial plan.

Lesson #4: Explore third-party migration tools.
Office 365 includes built-in migration tools. And those tools are helpful and well-designed -- if you’re migrating off Exchange. If you’re migrating off a different email platform, the built-in capabilities aren’t as helpful.

Because we were on Gmail, our only free option was Office 365’s IMAP migration. Unfortunately, the tool doesn’t let you transfer contacts or calendar items. Moving those items requires a third-party product. For $10 per user, we chose Quest Software’s OnDemand Migration for Email. This fully cloud-based product required only two clicks and two passwords to transfer everything and works seamlessly in the background.

Lesson learned: Never discount the usefulness of third-party products, even though they cost extra.

Lesson 5: Don’t ignore your need for proper technical support.
We also chose Plan E3 over P1 because our need for technical support was greater than what was available for free through P1 online.

Microsoft has mountains of documentation on Office 365, including walk-through videos and an unending stream of forum posts. However, we found the sheer mass of content overwhelming and the quality of Microsoft’s videos to be surprisingly poor. That’s all you get with P1.

Microsoft partners themselves are also still learning this system, so the quality of their assistance may be spotty as well. Microsoft’s technical support -- in accordance with their E-series plans -- is top-notch, quick to answer calls and specific with resolutions.

Lesson learned: Cheaper plans mean much less technical support.

Lesson 6: Create a URL cheat sheet.
My main gripe with the Microsoft Office 365 suite is the array of URLs needed to locate its various components. For example, SharePoint starts at and Outlook at Administering your Office 365 account starts at and usernames end with the suffix.

Additionally, SharePoint settings are administered via <yourSubDomain>, while Exchange servers use nonsensical names like Adding to this difficulty is the fact that each Office 365 component’s UI feels detached from the others. Simply put, I wish the entire experience was a bit more cohesive.

Lesson learned: Create a URL cheat sheet, because until Microsoft unifies URLs and UIs, you -- and your users -- will need it.

Lesson #7: You still have to administer SharePoint.
Because our company uses a different document collaboration suite, we were blindsided by SharePoint’s intrinsic complexity in both administration and use.

Inviting outside contractors to join our workspace required numerous settings in equally as many locations, including one requirement we never found in the online documentation. Also, building the workspace required no fewer than two complete tear-down-and-restarts. None of these are SharePoint’s fault; they are our own because of our lack of experience. If you’re not familiar with SharePoint, prepare yourself, and start learning before fully migrating to Office 365.

Lesson learned: Even though SharePoint is hosted, you must familiarize yourself with SharePoint administration.

Was the move to Office 365 worth it?
In a word, “yes.” While we can’t ignore a few of the inconveniences and minor gotchas, our experience with Office 365 has been pleasant thus far. My company already benefits from Office 365’s holistic approach toward document management and unified communications. We look forward to a lengthy and fruitful month-to-month relationship.

Greg Shields,
MVP, is a partner and principal technologist with Concentrated Technology. An IT industry analyst, author, speaker and trainer, you can find Greg at

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