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After years of anxious wandering in the wilderness of cloud services, many workplaces have finally arrived at the promised land: stable, secure, scalable, cost-efficient IT infrastructure in the cloud. But some who made the journey are still struggling to settle into this new technology. Most expected the environment to be somewhat unfamiliar at first, but they may find the newfound freedom of the open cloud so intimidating that they’re afraid to venture far from the home screen.

Indeed, a recent Gartner Research survey found that while enterprise customers are generally adopting more of Microsoft’s Office 365 cloud service suite, they still only consider two of those components (Outlook email and online Office ProPlus applications like Word and Excel) to be consistently valuable to business. In other words, users are trying out these new solutions, but they aren’t necessarily figuring out the best ways to make them fit into their business processes. Considering that Microsoft has estimated 80% of Fortune 500 companies use Office 365, this could pose a serious problem for enterprise productivity.

For those who’ve worked so hard to guide these pilgrims to their destination, it’s tempting to feel frustrated by their persistent hesitation to take advantage of the resources which would dramatically enrich their working lives. But it’s important to remember that old habits die hard, and although we may have made it safely to the cloud, the discoveries— and challenges— are far from over.

“There’s a baseline of value to switching to the cloud,” said Craig Roth, the author Gartner’s report on the survey. “But the real value comes when you start changing your work processes to take advantage [of Office 365] to its full extent.”

It’s true that the services provided by Office 365 touch so much of users’ day-to-day work that it’s impossible for them to miss it. But by the same token, there are so many features available, with more being added and adjusted every week, that it’s unlikely any user is making the most of everything on offer. Meanwhile, some users have been so thoroughly conditioned by bad experiences with legacy systems, that even when you try to share the good news about the convenience of these new services, they might not believe you.

“Lack of value from the broader panoply of Office 365 options is due to a confluence of factors,” Roth’s report explains. “The difficulty of changing the habits of information workers, an overabundance of ways to collaborate or share content, lack of funding to support change management efforts, and inability to understand how much time is lost or value could be gained for functions that are not well understood.”

MIL understands it’s not enough to merely reach your destination in the cloud. It’s just as important to adapt your business processes to help users thrive there when you arrive, and to continue exploring the new and ever-changing environment to fully develop its potential. Delivering organizational change of this magnitude requires a commitment to training and process support that extends well beyond the frontier of cloud migration.

So, what can be done to improve the value of cloud services in which your business has already invested heavily? MIL has identified a few best practices from our own experiences that may prove helpful:

Loop everyone in.

“Disruption” is often used as a positive term today, but for many of the overwhelmed and understaffed offices, it’s still a dirty word. Forcing users to suddenly learn a brand new solution that isn’t a one-to-one replacement for their existing tools can be hugely disruptive, and may make many shy away from using more than the bare minimum functionality. Instead, try catching your users’ interest by presenting common situations where your solutions become invaluable, and build on their understanding from there.

Users will likely learn for themselves (sometimes by accident) that they can attach OneDrive for Business documents directly from Outlook, even if they’re on their home PC or mobile device. But they may not realize that with just a few extra clicks, they can seamlessly launch those same documents in a full-blown Office ProPlus document editor in their browser or mobile app, and edit them with nearly all the same features they’re accustomed to on their office workstation. This kind of “business loop” enhances the value of these Office 365 components when they’re used in tandem.

Your “lasso” for tying together these new solutions should connect to real-world use cases. In training and guidance materials, invite your users to imagine a situation they’re likely familiar with. For example: Picture a lunch meeting interrupted by an urgent, unexpected data call. Before Office 365, you might have had to cut things short, scramble to pay your bill and rush back to the office to locate and prepare the requested documents. But thanks to OneDrive for Business and Office ProPlus, you now have the option to simply excuse yourself for a moment, pull up the documents on your mobile device, make any necessary edits, and send them off with plenty of time to rejoin your colleagues at the table.

Keep the fire burning.

After the hard work of cloud migration is complete, the user manuals have all been distributed, and all systems are operational, it’s all too easy to dust off your hands and call it a day. However, if you want users to embrace the solutions you just worked so hard to implement, this is no time to put out the flame of progress. Your best opportunity to impress upon users the usefulness of new technology is while it’s still fresh in their minds from the migration. As the saying goes, strike while the iron’s hot— but more importantly, you can keep it hot by hammering away at it until you’ve forged a strong, sharp understanding of how best to use your solution.

Sure, you likely scheduled training sessions and demonstrations in the weeks immediately before and after your migration. But what about the users who never bothered to attend? What about the users who only have questions weeks or months later, after they’ve had a chance to try things out at their own pace? What about new employees who never had a chance to attend your sessions at all? The best way to capture all these demographics is to be persistent and consistent in your messaging. For example:

  • Does your organization send out announcements about flexible leave policies in advance of a holiday, weather event, or other disruptive occasion? Take the opportunity to include a reminder about all the great the telework-friendly features that Office 365 has to offer. Users who finally try out your solutions to their fullest during these events often go on to continue using them under less extraordinary circumstances.
  • Have you scheduled a regular call with business unit representatives to check in on their IT questions and concerns? If not, get one on the calendar… and if so, consider increasing their frequency following a major migration to quickly intercept any issues and ensure their training needs are satisfied. This is also a great opportunity to propose valuable uses of your solutions tailored to individual departments’ unique requirements. These liaisons may then become technological evangelists for the rest of their business units, spreading your solutions to far more people than one small IT team could hope to reach.
    • Have you surveyed your users about the new solution? Not only is this a good way to gauge adoption rates and usage trends, but it can also be a clever method of teaching users about your solution without them even realizing it. For example, you might ask “Were you aware that you can selectively share access to your files and folders with other OneDrive for Business users so you can collaborate on documents?” They might not have known that before they read your survey— but they do now!

Clean out the cobwebs.

While setting up an exciting new cloud solution has obvious appeal, one important task too often falls to the wayside: cleaning up after the old, obsolete legacy system it’s replacing. This isn’t just a matter of decommissioning dusty old servers and locking up the datacenter; it also requires changing years’ worth of built up bad habits and outdated techniques that went with them. You might have written shiny new documentation to introduce your new cloud offerings – but did you remember to help your help desk update their customer support scripts? What about your HR onboarding processes and forms- do they give new users a fresh start on your new platform, or contain outdated, confusing references to systems that should have been laid to rest? If your customer support center is still telling users they should use a remote desktop solution just to access their email and files when teleworking, all your hard work could be for naught.

The lingering traces of legacy systems won’t always be obvious or emerge immediately after your migration, so it’s important to stay vigilant and try to intervene as soon as you notice them. For example, your users may know that they can easily insert a Skype for Business meeting link into their Outlook calendar invites- but do they realize that Skype for Business meetings can handle all of their video and audio teleconferencing needs in one place? All too often, meeting organizers will still include clumsy, external conference bridge dial-in information in their invites out of habit, with Skype for Business meeting links being included as an afterthought that may not even be used. When you see something like this, seize the opportunity to gently but firmly remind those users that better things are possible. If they push back on your advice, you might learn about a shortcoming of your solution that you hadn’t considered before, and can work with them to fix it. You may find that even Microsoft still has some cobwebs to clean out of their own solutions.

Perhaps the most essential part of changing old habits is to practice what you preach. If your own IT team can’t be bothered to take full advantage of the solutions they implemented, why should anyone else? Likewise, if you’re neglecting to regularly use some aspect of your solution, you may be in for a rude surprise when a patch changes or breaks key functionality and your users know about it before you do. The more personally familiar your team becomes with the inner workings of your cloud solution, the better equipped they’ll be to handle feature requests down the line (or remind users that what they’re requesting is already possible). A technical team is more likely to become stuck in their ways about their least favorite parts of the job- so if you notice engineers awkwardly documenting standard operating procedures by sending copies of Word documents back and forth via email, you may want to encourage them to get with the program and collaborate in SharePoint or OneDrive for Business instead.


It can be tough to offer useful directions for successfully integrating cloud solutions because every deployment is different. There’s no one-size-fits-all cloud solution, just as no two projects or companies are exactly the same. It’s important to treat every migration like a brand new journey, carefully planned and cannily guided from start to finish and beyond. That being said, the paths that we take are becoming increasingly well-trodden, and we’re likely to encounter many of the same landmarks  and potential pitfalls  along the way. We hope that these suggestions will help you and your users settle in to your new home in the cloud, instead of getting frustrated and walking away from an amazing opportunity.

Happy trails!


About the Author

Tom King, MIL Business Analyst

Tom King serves as a project management and technical writing specialist for MIL. He has managed the implementation of numerous cloud services and solutions for federal customers, including Amazon Web Services and Microsoft Azure, Intune, Office 365, and SharePoint. He is a certified APMP-Foundation professional.