9 Questions to Consider Before Migrating to Office 365

Office 365 offers three great incentives for small and medium business IT departments. Low upfront costs, simpler licensing for multiple computers and products, and hosted Exchange are compelling reasons to take advantage of this cloud computing option. With that, here is what you should know before migrating to office 365 to keep operations running smoothly.

But it’s not always as easy as creating an account and following a step-by-step migration wizard; migrating can be tricky.

Below are nine questions to think about before your email migration begins. If would like to reach out to us about our Microsoft 365 migration services or if you have any questions, please feel free to reach out to us.

Pre-Requisite Questions

What is your current email solution?

The best place to start with your migration is to determine what your current email solution is. Most Office users already use Outlook, but this can have a huge impact on what your options are for migrating.

Do all users have Office 2010 or newer?

This is important, mainly because older versions of Microsoft Office might need to be upgraded before your migration can even begin, which can potentially become a huge expense and time sink.

If you have Office 2007, migration technically still works, but you will run into calendar issues, or other important data that is unable to transfer over, resulting in its loss. Any other version below 2007 will simply not connect to Office 365 for data migration.

Questions You May Not Have Considered

Do you have access to change your Domain Name System (DNS) records?

This is one of the simplest parts of a mail migration, but can also cause the biggest delays. If everything is well planned and goes as expected, this is probably less than an hour of work, but when you do not have access to your DNS records the process can come to a screeching halt.

When you make the switch to Office 365, you will need to access your DNS in order to prove you own your domain and to direct email to your new mailboxes. Otherwise, every other server in the world would still be sending to your old server, which would be decommissioned. It’s like when you move to a new physical home address, you have to notify the mail client (USPS) of your new address in order to receive your mail at that location.

Do you have devices or applications relaying email through your current email solution?

If you migrate your server without thinking about the devices (such as any wide format scanners or technical printers) and applications that link to it, post-migration woes are in your future, as network scanning tools start to return failure notifications and printers and scanners start e-mailing your scanned document to nowhere.

This is something that you need to be aware of before migrating to office 365, and have a plan of action for before starting down the migration path, or you could suffer from more headaches. Perform an inventory of the services and devices that are linked to your current e-mail server and be sure to point them to the new cloud server.

Is password compliance going to be an issue?

If you don’t have a password policy in place, you may be using something like PASSWORD123 to login. This is extremely insecure, and while you may have been able to get away with this on your on-premise email, when you switch to Office 365, where your email is accessible over the internet from anywhere, there will be a larger chance for someone to hack your password.

Luckily, complex passwords are required in Office 365. Your new password will have to be at least 8 characters, including each of the following categories: upper case, lower case, numbers, and symbols. Also, by default you will be asked to change your password every 90 days. Generally, a sync is performed between your on-premise and Office 365 when migrating, so you won’t have to worry about multiple passwords.

Will losing your autocomplete file, signatures, or reattaching PST (personal storage) files be a problem?

When you reconnect to your new mailbox, these functions that you have set up in the past could disappear. You need to determine whether this will be a problem for you, or if you can simply just recreate them.

If needed, these can be migrated over, but it will require extra work, especially for the autocomplete. It’s a good idea to account for these in your migration plan, whether you decide you need them migrated over or not.

Is calendar sharing heavily used?

If calendar sharing is a feature that is heavily used in your organization, you will need to plan for this as well. Permissions for sharing your calendar with others may not transfer to Office 365 automatically, so if you have several calendar sharing schemes setup, you will need to carefully map them before starting your migration and ensure that you have a backup, just in case.

Questions That Are A Little Outside of The Mail Migration

Is there currently an antivirus or anti-spam gateway with blacklists, whitelists, etc., and do you want to keep it?

If you already have an antivirus/anti-spam email gateway in place, consider whether you want to continue using it with Office 365. Office 365 has its own antivirus and anti-spam solutions to keep your email safe, but your users may be used to their old solution. Take into consideration the custom whitelists and blacklists that may have been built up over the years, will you be migrating those over, and if so, how? This will be a choice that is unique to your organization’s culture and resources.

Would you like to implement new features such as encryption, data loss prevention, or e-mail archiving?

Is there anything missing from your current email solution that you would like to use for your new one? A migration to Office 365 is a great opportunity to audit and overhaul your e-mail services with new features and security.

Some of the new email features that you may want to take advantage of include encrypted email, data loss prevention (DLP), and archiving to name a few. You can purchase these individually, but package plans would get you more bang for your buck. What’s great about these is you can very easily turn them on or off whenever you need to, allowing you to only pay for what you use, when you use it.

Migrating to Office 365 offers convenience and cloud advantages, in a pay for what you use model, but you must be prepared for any hiccups you might experience. You will most likely be asked these above questions, and having answers will help the process go more smoothly and get you in your new environment faster.

Posted By: Tony Robison, Director of Technology