By now, there’s little doubt left that Microsoft Office 365 can make a significant difference to your business, yet you’re still hesitant to pull the proverbial trigger when it comes to migrating your emails from POP/IMAP to Office 365 in the cloud.

Don’t worry, you’re not alone.

Despite the impressive range of benefits to be gained from making the move (such as smarter, more flexible working and greater cost efficiencies), scores of small business owners haven’t made the move because the process of doing so has a reputation for being pretty difficult.

Is that reputation warranted?

How easy is it to migrate to your email to Microsoft Office 365?

Those are questions we’ll clear up today, along with offering some expert advice on how to carry out a smooth, hassle-free migration to Microsoft’s game-changing cloud productivity suite.

The Truth About Migrating to Cloud-Based Email

So, how easy is it?

The truth is, that unless you’re a sole trader or rank among the smallest of small business, it can be a complex, and often time-consuming process.

Those with a limited number of users will, naturally, find that though the process is still a technically-demanding one, it can be straightforward to use a process called partial redelegation to keep ownership of your domains and hosting an Active Directory for redirect specific domain functions (in this case email) to Office 365 cloud servers.

From there, the process can be carried out using the wealth of documentation, deployment tools, and user interfaces already supplied by Microsoft, though beware that at least some level of technical know-how is required even at this stage.

For growing SMBs and large-scale enterprises, the process becomes even more of a challenge.

The good news, is that there are a few things you can do (besides outsourcing email migration to an external IT company) to make the move much less hassle.

Choose Between Cutover, IMAP, or Hybrid Migration

There are essentially three different approaches to migrating your email from an Exchange Server to Office 365.

For small businesses with less than 1,000 mailboxes, Cutover migrations are by far the easiest, though keep in mind that easy may not always mean best. Since cutover migrations need to be carried out all in one go (rather than in batches), you may find that migrating lots of large mailboxes in one move results in more downtime than your business can afford.

If you’re transitioning to the cloud from a different mail system other than an existing Microsoft Exchange server, then you may find that IMAP migration is the best alternative. On the plus side, this can be staged t reduce downtime. However, it’s worth noting that with this method, you’ll only be able to move actual messages and nothing else, so if calendars, tasks, and contacts are important to you, you may want to opt for the third alternative.

That alternative is hybrid migration, which works by creating a connection between your local Exchange server and Microsoft Office 365. Though this is the most complex method to carry out -and often requires the skills of a qualified cloud migration specialist- it does offer the most flexibility and robust option for larger SMBs.

Plan How Long You’ll Need and How You’ll Manage Downtime

Downtime -even for a brief period- is largely unavoidable no matter which migration route you take. So, where possible, you may find it useful to schedule your migration for outside of office hours.

Where that isn’t possible, it pays to estimate how long the transition will take, what impact that will have on your business, and what you can do to speed up the process.

Helpfully, Microsoft offers a performance chart to show you which should help you determine how long your migration is going to take.

You’ll notice that throttling (a purposeful restriction of the process which results in a smooth migration) can slow things down, whilst access to greater amounts of WAN bandwidth can increase performance.

Run Microsoft Readiness and Connectivity Checks

Once you’ve done everything you need to do to prepare for your migration, it’s worth checking that you’ve done everything correctly and you’re ready to go.

Fortunately, Microsoft provides a helpful tool which does just that. It’s called the Office 365 Health, Readiness and Connectivity Checks tool and it can be used to identify any potential problems with your migration before it’s carried out, and even run repairs so that you’re truly ready to go.

Carry Out a Test Run First to Identify and Iron Out Any Issues

You’ll find lots of detailed instructions online about how to carry out each different type of migration, but even if you’re sure you’ve followed everything to the letter, there is still the chance that unexpected problems can occur.

With that in mind, it’s important to carry out a migration test or ‘dummy run’ first.

Start by creating a small selection of fake accounts, each one with its own messages, contacts and calendars. Carry out a small email migration to Office 365 using those. Then, if everything goes well, choose a small selection of mailboxes that represent the broad cross-section of your user base (small accounts, large mailboxes, and everything in between).

You can then do a second test run using those accounts.

Once that’s done, give yourself some breathing room to analyse how the migration went, if any problems occur, and how you can solve them.

With that done, you can finally carry out the rest of your migration and start seeing for yourself what a significant difference Office 365 can make to your business.