Office 365By now you've almost certainly heard about the license donation program for Office 365. Most nonprofit organizations can get free access to hosted email (Exchange), files (SharePoint & OneDrive), and instant messaging (Lync) in the cloud from Microsoft. These are the same tools that many nonprofit organizations have been using for years, but are now hosted for free in the cloud.

Getting the donation is easy, after first requesting a free trial from Microsoft then getting validated for the full donation through TechSoup, but moving your organization's data and getting everyone comfortable is a little more work. In many cases organizations without an IT staff can make the change, but depending on your comfort level, your size, and your complexity, you might need a little help.

A couple of weeks back, I presented on a webinar with TechSoup discussing the process and challenges of moving your organization to Office 365 without leaning too heavily on an outside consultant. You can view that full webinar below.

Today I'd like to help you decide if your organization is ready to make the change.

Full disclosure: My organization, Tech Impact, is a 501(c)(3) that offers technology support exclusively to nonprofits. That includes full-service migrations and low-cost DIY workshops. My goal here isn't to sell either of these options, it is to help your organization decide if you are ready to move yourself to Office 365 and what kind of support you might need if you are not. Everything here should apply if you do the work yourself or pick any third party organization to help.

Also of note, Office 365 is an umbrella marketing term that covers several different tools. Below you'll find important questions to ask when determining if you need help moving your organization to that portion of Office 365. Keep in mind that moving to Office 365 will require a great deal of research and planning -- even if you end up doing all the work yourself.

General Office 365

Do you want to integrate Office 365 with your on-premise servers?
If you want to create users on your local server and have those users get synced up to the cloud or if you want to synchronize passwords between your local server and the cloud, you'll need to implement Directory Synchronization.

Directory Synchronization requires an extra server, keeping your exchange server around indefinitely, and possibly changing how you end up migrating your email, calendars, and contacts to Office 365. If you are set on putting in place this integration and don't have an IT staff with significant active directory experience, you will probably need help. 

Note: I strongly recommend against integrating on-premise servers with Office 365 if you have fewer than 200 users.

Email, Calendars, and Contacts (Exchange Online)

Do you have fewer than 20 mailboxes?
If you have fewer than 20 mailboxes and already use Outlook then you are a good candidate for a simple PST import/export migration. With this type of migration you just create accounts for each of your users in Office 365 then export their email from Outlook to a PST, configure Outlook for Office 365, and re-import the mailbox. It could not be simpler. If you have fewer than 20 mailboxes, have heard of MX records, and already have your email in Outlook or can get it there, you don't need any help. Otherwise, you might need an hour or two of someone's assistance to get you started.

Are you willing to move everyone's mail over at the same time?
If you have more than 20 mailboxes you will need to use automated tools to make the migration practical. If you are willing to move everyone over at the same time then you can perform a "Cutover" migration. Cutover migrations can be used to migrate data from Exchange servers and IMAP email providers and are relatively straightforward.

However, you'll need to get all of your users switched over at the same time -- you can't do a few at a time. If you have some limited Exchange server management experience, understand DNS, and are willing to move everyone over at the same time, you should be able to complete the work yourself. Otherwise you might need some help configuring your server for the migration. 

Do you need to move a few user's over at a time?
If you need to move your users over slowly, because of political concerns or a large number of mailboxes, you will need to perform a Staged migration or configure Email Co-Existence. Both of these require Exchange and Active Directory Expertise and will require you configure Directory Synchronization. Do not attempt this kind of migration on your own if you do not have a senior network administrator on-hand to manage the technical aspect of the project.

Shared Files (SharePoint Online) 

Do you have a lot of time to explore SharePoint?
Unlike Exchange Online most people do not have extensive experience with SharePoint. SharePoint is a complicated tool with a ton of features and a somewhat confusing interface. Understanding what it can and cannot do - particularly when it comes to integrating with locally installed versions of Office - can take a tremendous amount of time and trial and error. Once you know what you are doing it is easy to configure, but the understanding does not come easily. If you are not already familiar with SharePoint and do not have the time to figure it out, you should consider getting help from a third party that does.

Do you have the political capital to push through a major change?
SharePoint does not work like a network share. Your users will need to access their files at least partially through a web interface and generally change their behaviors. It is not always easy to convince an organization that the change is worth the benefits. If you have a change-adverse organization or have trouble getting fellow staff members to see the benefits of new technology, you should consider getting help from a third party to help with the migration, training, and adoption.

Personal Files / My Documents (OneDrive)

OneDrive has a very basic feature set that is straightforward to use. Its ability to be synchronized to a file on your local computer makes it easy for users to understand. Every organization should be able to implement OneDrive without the support of a third party organization.

Instant Messaging (Lync)

Do you understand DNS?
There is very little configuration required with Lync. Every user simply downloads a client and then is able to log in and access all the features of the service. However, a number of DNS records (including SRV and TXT records) must be added to allow Lync to work properly. If you are not familiar with DNS then you should consider getting help from a third party. No more than 1 or 2 hours should be required.

For more information, feel free to watch the full 90-minute webinar posted below, where I walk through these points in more detail and with some key decision points outlined.

Are you moving to Office 365 at your organization? Share your lessons learned in the comments below.