If you have a business to run, the last thing you need is a
server to manage. That’s the fundamental appeal of cloud services, which take
away the hassle of paying for expensive hardware, managing licenses, patching
software (and worrying about the consequences if you don’t), and fielding calls
from angry users when something goes wrong.

Office 365 could be the poster child for this new wave of cloud services. Instead
of managing your own Exchange and SharePoint servers, you let Microsoft do the
hard work in its data centers.

For large enterprises, this is a matter of shifting
on-premises servers to the cloud, and Microsoft’s online services were
originally designed for this class of customer. But the latest release of
Office 365 makes these same capabilities available to small businesses, even
sole proprietors, in a subscription-based service that doesn’t require any
local servers or complicated license management schemes.

In this article, I’ll walk you through the process of
setting up Office 365 Small Business and Small Business Premium. Small businesses typically
don’t have a dedicated IT staff, so all the steps I outline here can be
performed by an IT consultant who has the requisite networking skills and then
managed by a tech-savvy business owner, using the dashboard shown in Figure A.
The entire process can be accomplished in as little as a few hours.

Figure A

Before you begin

The best way to ensure that a move to the cloud goes
smoothly is to do some homework first. To determine your business needs, start
by asking five questions.

1: How many user
accounts will you need?

The maximum number of users you can support with either of
the Office Small Business products is 25. If you anticipate that your head
count will expand beyond this size in the next few years, choose the Midsize
Business plan (maximum 300 users) or one of the Enterprise plans instead.

2: How many users
need email and cloud storage only?

Each one of these users will need a subscription to Office
365 Small Business. On a month-to-month basis, the cost is $6 per user per
month. You can discount this price to an effective rate of $5 by paying in
advance — $60 per user per year. The licenses are fully transferable, so if one
employee leaves and is replaced during the subscription term, you can transfer
the license with a few clicks and no extra cost.

3: How many users
need access to the latest version of Microsoft Office?

The Office 365 Small Business Premium subscription includes
the same email and cloud storage services as the Small Business offering but
also gives each user with an active subscription the right to install the
latest version of Office from the cloud on up to five PCs or Macs. The cost is
$15 per user per month; an annual subscription costs $150, for an effective
cost of $12.50 per month.

4: Do you need to
migrate data from other servers or services?

The simplest scenario is a clean startup for a new business,
without worrying about email archives or history. If you’re willing to give
your business a completely clean start, the setup process is extremely simple.

Most businesses, however, have email archives they want to
maintain. For those scenarios, you have a variety of migration options, which I’ll
cover in a minute.

5: Do you anticipate
that you will need any enterprise-specific features?

Most small businesses don’t need to worry about this, but it’s
worth perusing the detailed feature checklists of all Office 365 editions to be certain you haven’t
overlooked something. In particular, you’ll need to consider an Enterprise plan
if you want to keep a mix of on-premises and cloud-based Exchange or if you
want to use the Yammer social networking service. In addition, any business
that is subject to statutory restrictions that require formal compliance and
discovery regimens should consider the Enterprise offerings.

With those planning steps out of the way, it’s time to get

Step 1: Create an Office 365 organizational account

This is a simple process that involves two steps.

First, you need to create your Office 365 organizational account.
This is where you’ll supply basic information about your business, including
the crucial payment details. Start by filling in the required information here.
(If you prefer to create a 30-day trial account for evaluation purposes, start here.)

Most of the details are straightforward: your name, company
name, address, and so on. But two gotchas are worth noting:

  • In the Email field (see item 1 in Figure B), be
    sure to enter an address that is not associated with the domain you plan to
    migrate. Otherwise, you risk losing important messages during the migration
    period. A free webmail account (Outlook.com or Gmail, for example) works well.
  • Choose the subdomain name (item 2) carefully. The
    default entry is based on the Organization name you enter, but you can change
    it to whatever you prefer. After your account is created, you no longer have
    the option to change this value.

Figure B

Be sure to set a strong password, one you don’t use anywhere

You can log in to the Office 365 dashboard immediately by
visiting Office.com and entering the username and ID you just created. For your
first visit, you should go straight to the administrative dashboard. And be
prepared to wait a while before commencing the next step. In my experience, it
can take an hour or so before your services are available.

Step 2: Purchase licenses

Although you can skip this step until later, I recommend getting
it out of the way now. Clicking the Licenses link on the dashboard takes you to
a page that allows you to add licenses. (You’ll assign those licenses to user
accounts later.)

As you can see in Figure C, you have two options for adding
licenses to your account:

  • Enter a product key.
  • Buy a new subscription directly from the
    dashboard using a credit card.

Figure C

Step 3: Set up user accounts and assign licenses

The workflow for setting up a single user is fairly simple. Click
the link under the Users & Groups heading on the dashboard and begin
filling in the forms (Figure D). The steps involve entering full names and
usernames for each user, assigning their location, and assigning a license, if
you’ve purchased them already.

Figure D

A few tips worth noting:

  • You can add extra details about each new user,
    including their job title and phone numbers, by clicking the Additional Details
    link. Or you can set this task aside for later if you prefer.
  • The second step of the wizard allows you to
    designate a user as an administrator. Note that your account — the one you
    created with your organizational account — is already an administrator. For
    Office 365 Small Business accounts, being an administrator is an all-or-nothing
    proposition, with the right to create and edit user accounts, reset users’
    passwords, and manage all service settings. This role should be reserved for
    only the most trusted employees.
  • The Create User wizard allows you to assign an
    Office 365 subscription to a user, with Exchange Online, SharePoint Online, and
    Lync Online included. If you want to omit one or more of those services for an
    individual user, you’ll have to go back after you’ve created the account to get
    the full group of settings.

Step 4: Migrate existing mail/calendar/messages

This is potentially the most confusing step, so it’s worth
studying these instructions carefully.

As I noted at the start, you can skip this process
completely if you’re willing to start your new email accounts from scratch. However,
if you have existing email, calendars, and contacts to migrate, you’ll need to move
them from their current location to your newly set up Office 365 server.

There’s a complicated process for automating this migration
using the secret Exchange Control Panel, IMAP settings, and a CSV file. (I’ll
explain how to do that in a follow-up article.) But if you’re migrating only a
handful of users it’s easy to accomplish this task manually.

Before you start migrating an individual account, I
recommend that you forward all incoming messages from its current mail server
to the new Office 365 address (username@organization.onmicrosoft.com). This step
ensures that the user associated with that account doesn’t miss any messages
during the migration process. (Don’t worry, those forwarded messages will be
there later when you change the default email address for the account to one in
your custom domain.)

Next, you need to save the contents of your existing mailbox
to an Outlook PST file.

  • If you’re currently using Microsoft Outlook
    (version 2007 or later) with a POP account, your email is already in a PST
    file. You just need to locate that file and use it for the import step I
    describe later.
  • If you’re currently using an IMAP account
    (including Gmail), you’ll need to configure Outlook to connect to your mail server
    and download all messages from the server. Caution: Make sure you check the
    account settings carefully. If you want to migrate all your old messages, you’ll
    need to ensure that Outlook’s Mail To Keep Offline setting is set to All.

With all your existing mail saved in Outlook, follow these
steps to save those messages for import:

  1. From Outlook’s File menu, click File, Open &
    Export, Import/Export. That opens the dialog box shown in Figure E.
  2. Choose Export To A File and click Next.
  3. In the Export To A File dialog box, choose
    Outlook Data File (.pst) and click Next.
  4. Choose the set of folders you want to export
    from. If you want to save every bit of data, choose the top-level folder and
    make sure the Include Subfolders box is selected, as shown in Figure F.
  5. Choose a location and a filename for your PST
    file. Don’t use the default file location or filename — those default settings
    are buried deep inside the logged-on user profile and are hard to find.
  6. Give the PST file a password if you want to add
    rudimentary protection to it and then click Finish. The save operation begins
    immediately. Be sure to leave your computer running and Outlook open until the
    operation is complete.

Figure E

Figure F

Do this for every user you plan to migrate. When you’ve
successfully backed up all your email accounts, you can move on to the final

Step 5: Make the move

The final step is to attach your business’s custom domain to
your Office 365 account and assign email addresses in that domain to your user

Getting over this last hump requires that you have access to
the nameserver and DNS settings for your business domain and the expertise to
edit them. (If you don’t have those skills, it’s time to call in an expert.) It
also requires a bit of patience, as you’ll need to wait for your changes to
propagate through the worldwide network of DNS servers.

Because GoDaddy and Office 365 have a partnership, the
process for transferring a domain registered with GoDaddy can be done
automatically, as shown in Figure G.

Figure G

For domains that are registered elsewhere, you first have to
establish your ownership of the domain name by creating a single DNS record
that Office 365 can use as verification. After this step is complete, you have
a final choice to make:

  • You can move all DNS settings to Office 365 and
    create any custom DNS records in the Office 365 interface. (This option is not
    available for Office 365 Enterprise plans.) If you don’t have any external
    resources that depend on the domain name, such as an existing website, this is
    by far the easiest option. All you have to do is change the nameserver records
    at your domain registrar to point to the Office 365 servers using the values
    supplied in the Domains dashboard.
  • If you prefer to manage your DNS externally, you’ll
    need to create DNS records at your domain registrar. Microsoft includes detailed instructions for more than 20 commonly used domain registrars.

After you’ve made the necessary changes, wait for Office 365
to tell you the changes have been propagated successfully. You can check at any
time by selecting an entry from the Domains list and then using the Domain
Troubleshooter. If there are problems, you’ll see specific information on what
needs to be fixed. If everything’s clear, you’ll see a message like the one
shown in Figure H.

Figure H

With the custom domain attached to your account, you can now
open each user account and replace those generic Office 365 addresses with usernames
in your custom domain. The domain setup wizard lets you do this automatically
for all the users in your organization. You can also change addresses manually
from the Users section of the dashboard.

Once all that is complete, you’re ready to go. Any user can
access his or her Office 365 services from a web browser by signing in at
Office.com. You can also set up Outlook using the newly created email addresses
and import the mail you saved in Step 4. (The Import wizard is on the File
menu, in the same location as the export options. Just choose the option to
import from a file, point to the saved PST file, and wait for the import to

Your imported messages will be synchronized from Outlook to
the Office 365 server, allowing you to access them from anywhere.