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Out Of Office: Setting Expectations for Office 365

Level 9

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?


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.


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. Do you have any tips to share? Maybe you've run into some unexpected issues along the way and can share your experiences. Feel free to leave comments below!


MS made it appealing for us to move to the cloud.  They cut our Office licensing by $6M annually to dump our local servers and move our documents and e-mail to the cloud.

After doing that, e-mail performance drags, accessing documents is unpredictable, and I get a lot less work done.  No additional budget was added from those "savings" for us to purchase cloud-based monitoring tools, so we can't even nail down the cause of the slowness.

I regard it as a mistake, but I can't push back against $6M.  Hmmm, 17,000 employees times X amount of productivity, multiplied by hours per week of lost employee time . . .  And this is the medical field.  Some of those employees aren't making minimum wage.

Include the lost productivity for our IT staff trying to fix the unknown, and for our Help Desk fielding all the extra complaints, and include ISP's and WAN providers who don't route all traffic through the same interfaces (which results in some traffic being slowed by GBIC problems, while other destinations are always fast--what a nightmare troubleshooting!).

I'd go back in a heartbeat.  Sure, we had hardware to maintain, licenses to maintain, data center floor space to pay for. 

But Office was always fast, your documents were always quick to open, e-mail was always fast.  The cloud promised much, has yet to deliver anything close to what it's taken away.


Ahh, the joys of the cloud.... 

The service is up and available...just not as responsive as you would like. Not their problem as the up and available part are met.

Is it worth the savings ?  Maybe, for now.


Nice write up

Level 14

I went to O365 in October, migrating from a non-MS mail system with an Outlook connector.

On the plus side:

Common Outlook configuration



Common versions of office (we used to maintain 2)

Easier administration

Easier remote access including via phone.


Elimination of the other "supporting" applications and appliances for email.

On the minus side

The speed issue and lack of tools

We are only @100 users so I don't have the complexity of  rschroeder​ 's  environment, but it seems the issues are universal.

It was a good move for us.

Level 13

good Article

I'm glad to know the experience is a positive one for some companies.

When we started migrating 17,000 employee's Outlook mail boxes to the cloud, the load overwhelmed our firewalls' ability to process packets through DMZ interfaces. We had to reduce throughput, and then turn off inspection on that outbound traffic, since it was also impacting all DMZ traffic, and also much of our corporate Internet.

Truly, a learning experience in many areas--not all of which were properly anticipated.

Level 20

I'm kinda dreading when O365 becomes usable by the defense industrial base.  I think it is coming though anyhow.  I guess one good thing is we could perhaps put some Orion agents in these new specialized clouds to report on some stats... at least I hope that's possible.

That hasn't been our experience. Sorry it has been a negative for your org. Of course, we migrated from Lotus Notes, so our standards of satisfaction were already low.

As far as if it's a 'mistake' - yep, your org definitely made mistakes in lack of planning. There was no impact investigation done for your firewalls' abilities to handle the increased traffic and no demand planning for increased internet and WAN usage, apparently. Unfortunate. Of course, if those investigations had been done, perhaps the cost savings wouldn't have looked so rosy. Who knows?

Level 14

We have a hybrid solution with 50,000 students accessing Office365 via AD authentication on prem and ADFS through a portal.  5,000 staff on prem in Exchange 2010 who are about to go to Office365.  We will keep some high throughput mailboxes on Exchange 2016 on prem as Microsoft won't allow us to put them in Office365.  The students don't really care about the slow responses and downtime but the staff will go mental.  I keep banging on about monitoring but no one here is listening.  I know I can use WPM to monitor for up / down and Solarwinds are working on a better solution but I really can't see it going well.  I can't wait for the vice chancellor to kick off and then tell him there's nothing I can do.  It's been interesting getting our Identity Management solution to provision Office365 accounts and both Microsoft and a Gold partner have been very involved. 

It's all free at present (academic licences are currently free) but there has been a leaked memo from Microsoft where they discuss charging.  That will be very interesting. 

Level 13

Painful migration of Office365.....  Need better monitoring tools.

Just starting the O365 move. So far, the road has bumps.

Level 14

Bumps ?     Mine has bloody great pot holes and some of the bridges we have to cross haven't even been built yet.

We've started investigating Azure Express Routing to see if it can reduce the very poor performance for our Cloud-based MS apps.

Pricing - ExpressRoute | Microsoft Azure

Have any of you gone with Azure Express Routing, or chosen not to use it?

We have not yet, but we are also reviewing it

We moved to O365 about 18 months ago. There were some bumps and bruises along the way and we still have a bunch more to learn but it has been totally worth it. Next step for us is to move to E5 licenses and take advantage of UCAAS opportunities. The freedom of the burden of the on-prem infrastructure was worth it alone.


Level 14

keep us updated...

Level 20

We haven't done it yet in any sizable amount but for use express route is the ONLY way we'd be allowed to connect because our data can't traverse the public internet.  Hopefully that improves performance as well because some stuff I've read sounds like horror stories after switching to O365.


Expectations and testing.

Our experience has been good as far as performance is concerned - but then we only have 2500 accounts and a Gig to the Internet. The "hybrid" configuration that was chosen has made management much more difficult and convoluted and I don't really have a clear idea of what we are getting by having "hybrid."

Level 13

Level 21

rharland2012​ we have also have a very positive experience with O365 and Azure.  Our O365 is currently in a hybrid mode but we are also using cloud based SharePoint and it all works very well.  We also manage a lot of resources in Azure and that all works very well.