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Out Of Office: Setting Expectations for Office 365

For a lot of organizations, moving to Office 365 might be one of the first, or possibly biggest, migrations to a public cloud. There can be a lot of stress and work that goes into the process, with the hope that the organization will reap the benefits. But how can you be sure that you are, in fact, getting the most out of Office 365?

Know Your Problems

We typically don't carry out IT projects just for the heck of it. Enterprise IT departments almost always have a backlog to deal with, so deploying new technology just for the sake of it isn't very high on the list. Rather, most priorities are ordered by the problems that they solve or the value that they bring. Moving to Office 365 is no different. If you find yourself looking at making the move, hopefully, you have a list of perceived value it will bring. Sitting down with business leaders is a great starting point. Ask them what--if any--pain points they have. Maybe it is the lack of availability. Do they always need to be using a corporate-issued laptop to access email or work documents? Would SharePoint online solve that? Another common complaint that I have seen is older software. Sure, 90% of the features from Word 2003 are the same in Word 2016, but that doesn't mean everyone wants to use 13-year-old technology. In some cases, it can even be for perception. If a salesperson shows up to close a big deal and they are running Office 2003, how would that look? They certainly would not come off as a cutting-edge company. Subscription-based licenses from Office 365 can solve this and ease the burden of managing spreadsheets full of license info for IT departments.

What Challenges do you Foresee?

You've decided that the move makes sense. Great! What challenges do you foresee? This step is critical as there is almost always some cost associated with it. It might be soft costs, such as time from your salaried IT department. Or it might be hard costs; maybe you are looking at performing a hybrid installation and you'll need to increase your bandwidth costs. How about regulations? Do you need to make sure some data stays on-premises (i.e., financial data) or is it all safe to move to SharePoint? If the former, how do you plan to track and enforce compliance? There are tools built into Office 365 for compliance and security, but will it be a challenge to get IT staff trained on them? Another common challenge is user training. Lots of options exist for this, ranging from Microsoft-provided materials to possibly doing lunch and learn sessions with groups of employees over time. As most folks who have help desk experience in IT know, sometimes a small number of users can account for the majority of support time.


Now that you know what value you will be gaining, and the potential challenges, you need to do some math. Ideally, you can account for everything (monthly costs, infrastructure upgrades, lost productivity, etc.). Even better if you can assign dollar figures to it. Once you have that, the decision should become easier. Are you saving money? If so, how long will it take to reach your ROI? Are you going to end up spending more on a monthly basis now? Is the value worth it? Maybe your sales staff will be more agile and close more deals, increasing revenue and profit. This is by no means a comprehensive list for such a big project, but it should be a good starting point.
Matt Crape
Matt is an IT Manager by day in addition to a VMware vExpert, Veeam Vanguard, and Cisco Champion. With over 15 years of experience in…
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