Office 365 Review: Confessions of a Modern IT Guy

One of my responsibilities at Argenia is the office IT guy. More by necessity than by choice, but I don’t mind stringing cables and installing software as a break from the everyday.

Early on I saw a gap in how we handled email and managed shared files. Email was a POP service hosted by Bell Canada Business (trash) and file sharing was done on a rickety Windows XP machine with a death rattle. DropBox was being used to share files as well, but this proved costly when a virus swooped in and encrypted their files which then automatically updated their DropBox versions.

So, I figured I’d give Office 365 a try. We used the SharePoint elements at Agility and it worked well. I figured Argenia would get even more value out of it by using Exchange, which is something we hosted internally at Agility.

Getting Started

We started out with four users on Office 365 Small Business. Setting up the accounts was a breeze. Follow the prompts and it’s all set up in minutes.

Setting up the email was a little trickier. However, this was more a function of our domain provider than the Office 365 service. The setup guides you through all of the necessary settings, including the (quite complex) DNS settings. I highly recommend moving to a reputable domain provider like GoDaddy before attempting to switch your email over if you want to avoid interruptions. In particular, you’ll need to be able to add TXT records and be comfortable changing MX records. Bell Hosting didn’t allow TXT, but I thought I was clever enough to work around it. Not so. Email went down for a few hours which is always catastrophic. So I switched the settings back and initiated the transfer to GoDaddy. Once there, the settings took effect immediately and I was off to the races.

All told, it took about 4 hours of effort to get set up. It was easy to get agreement for the fees at a measly $5.00 per user per month paid annually.


Moving to Hosted Exchange

Once the accounts were set up, the first step was to migrate email. This was a reasonably straightforward task for a guy with a little IT experience. Outlook allows you to add multiple accounts, so you can add your Office 365 account alongside the POP account with no interruptions to your email. Simply add a new Exchange account, type in the email address, and Outlook takes care of the rest, assuming you have your domain set up properly. Depending on your versions of Windows and Outlook, you might have to do this through the Mail Control Panel, rather than through Outlook.

You can then drag emails from the POP account and drop them in the new Office 365 account, including sent and deleted items, and they will sync to Exchange. Don’t forget to copy over the appointments and tasks as well! I recommend switching the calendar to the List view under the View tab and ‘Change Views’ to make this as quick and painless as possible.

Once everything is moved over, you can go into the Outlook Account Settings and remove the POP account. Note that the PST file containing mail items for the POP account will remain on the machine, so you don’t have to worry about losing anything.

Bam. Cloud email.

File Sharing

I’ve been using SharePoint for many years and I’ve always appreciated the benefits of cloud access and auto-versioning of files. The ‘Sites’ function of Office 365 is the best version of SharePoint yet. Like all iterations of SharePoint, it’s not the most intuitive at first. But as a modern IT guy/gal, clicking around and trying things will get you what you need without too much frustration.

It’s important to plan your file system structure before you get too deep into the setup. I like to split up Document Libraries according to the departments in the company. For example, Sales, Marketing, Finance, Operations, etc. That way, you can restrict access according to the areas of business that are applicable to each user. You can also use sub-sites to segment files into separate brands. For example, Argenia has two main brands – ClearBlue and Argenia Railway Technologies. So, I used ‘Argenia’ for the main site with document libraries for things like HR and Finance, and then created sub-sites for ClearBlue and Railway and set up Document Libraries for the Sales, Marketing and other departments that apply to these brands. It’s probably overkill for a company with 6 people, but it’s a good idea to build these things in a way that will scale as you grow.

OneDrive for Business

Microsoft recently added OneDrive for Business (formally SkyDrive Pro) to the Office 365 line-up. Whereas in the past you would have to use the SharePoint web interface to access files, OneDrive allows you to sync files directly to your computer.

I was a little skeptical of this at first. The last thing I wanted to deal with was users complaining about their files being out of sync – or worse – their changes being lost. But, with our users having adapted to DropBox, they wanted something similar, and OneDrive offered this. So I gave it a try.

To get started with OneDrive, you simply open a document library in your ‘Sites’ area and click the ‘Sync’ button at the top right. A dialog pops up to take care of the rest, including the download of the OneDrive client. Make sure you download the right one. Files are then synced to a new ‘SharePoint’ main folder that appears in your Windows Explorer Favorites. File structures are set up according to your site name which is nice and clean. e.g.

Argenia – HR

Argenia – Operations

ClearBlue – Marketing

ClearBlue – Sales



From my experience so far, OneDrive has been pretty solid. I’ve encountered two problems so far. The first one wasn’t a big deal. One of the document libraries was too large for the sync engine and I was told so by an error on the OneDrive client. So, we trimmed it down, split it into two and we’re good to go.

The second was much scarier.  Windows Update kept failing on a bunch of Office updates on my laptop. While I was trying to fix that, I think I messed up something with the sync because it went completely out of whack. It seemed like the sync history was lost so it was trying to sync everything again. The entire set of files were in ‘failed to upload’ status in the Office Upload Center. It was a horrible feeling.

I managed to fix it by:

  1. Deleting the document cache
  2. Deleting all of the sync’ed files (or rather moving them to another folder)
  3. Deleting the Internet Explorer browser history
  4. Going into each document library and clicking ‘sync’ which recreates the sync’d folders
  5. Hoping for the best

It worked. Because of that, I thought it was best to sort out my Office update issues. I realized that I was running a copy of office that was licensed to Agility. I figured it would be prudent to align my Office license with the new company and the 365 service.

Upgrading Plans

So, I shelled out another $7.50/mo for Small Business Premium which includes full versions of the Office desktop software (Word, Excel, PowerPoint, Outlook, etc.) for just two of the users. Upgrading plans was not a straightforward process.

It took me a while to find the ‘Buy more licenses’ link which is buried under the User Profile edit screen. A screen which is next to impossible to find. I had to consult a blog post that informed me to click on the little pencil icon on the user screen. Obviously. From there it was easier.

The easy ways to buy licenses all scream for you to upgrade the license for all users. It’s an obvious tactic and I respect it – at least they still make it possible to upgrade individual licenses.

So you have to buy the licenses, move the users over to them, and then call support to cancel the Small Business licenses that were moved over to Premium. Otherwise, you would be double paying for the accounts that were upgraded. Not the most efficient process, but it works. The support number was responsive, the staff sharp. They even give you a direct line to your rep which you can call back at any time.  I’m sure the automation of this process will improve as the service matures. We’re still in the early stages of “retail” cloud services.

Office Apps On Demand

Once you’ve upgraded, you can download the Office desktop apps from your main site under Office 365 Settings and Software or from the Office download button on the Admin home page. You might have to wait a few minutes after the upgrade for the Office download to appear. It’s quick and straightforward to install the software once it appears. Make sure you click the ‘Advanced’ link and choose the 64-bit version if you’re on a 64-bit machine.

The package contains Word, Excel, PowerPoint, OneNote, Access, Publisher, Outlook, Lync and InfoPath – the full Office suite. I haven’t tried this, but it indicates that you can install the software on up to 5 machines. I’m guessing that has to be machines that you own as an individual, as opposed to sharing the software with other Office 365 Small Business users.


It’s been a couple of weeks since the upgrade and no problems sync yet. *knocks on wood*


Lync is an app that I had never used before Office 365. I got pretty excited about it because it seemed like a cheap and easy way to do web conferencing. In my Agility days, I did a ton of online demos and the WebEx and GotoMeeting bills were pretty significant. Lync integrates with Outlook and makes it easy to add Lync-based appointments to your calendar. Users can call into your Lync meeting through their computers for no charge. If you want to add a teleconference number available by phone, you have to add a separate service. That was a little disappointing, but I can see how this cost could spiral if Microsoft built this right into Lync. You can pick from several ‘approved and integrated’ teleconference providers when you access the ‘IM, meetings and conferencing’ section under Service Settings on the Admin page. I chose InterCall which provides world-wide calling for 10 cents per user per minute.


Public Website

In my opinion, there is no use for the public website capability in Office 365. Although there are many sites out there that use SharePoint as a CMS, it’s really not designed for public websites. Check out Weebly for your website and read about my pleasant experience with them here.

Mobile Integration

Office 365 has an extensive suite of apps available for all platforms. Being a Windows Phone guy, I probably get the best of them. They are definitely impressive. I use the OneNote app a ton and I’ve used the Word and Excel apps a number of times. When you’re on the go, it’s handy that you can bring up any document in SharePoint in minutes, rather than hauling out your laptop all the time.



The bottom line is that Office 365 Small Business and Small Business Premium provide exceptional value for your small business productivity needs. It might seem a little scary at first to sign up for a recurring software fee, but you get what you pay for – a true cloud service that requires minimal effort to set up and manage. Perfect for a modern IT guy who is wearing many hats.