Movement to the cloud is inevitable. With increased security, additional tools, and cost savings it’s becoming more and more of a no-brainer. Rarely are we faced with customers, after completing an honest assessment , who can’t go to the cloud.

However, it is important to become knowledgeable about what is available to you before you make that jump to the cloud.  This awareness and knowledge will be extremely helpful in avoiding pitfalls of a failed deployment, grumpy users, and challenges on getting traction on future initiatives.

Here are 5 things organizations do that challenge Office 365 deployment:

1. Lifting & Shifting When You Should Be Planning and Rearchitecting

Many organizations just want to take what they have on-premises and shift it over to the cloud.   That is the easy approach and while you may be thinking you are saving yourself on time in the long run you will be missing out on the benefits of moving to the cloud.  A lot of those team sites could probably be moved to Teams, a lot of those sub sites should now be site collections. Those InfoPath forms and SharePoint Designer workflows are something from the past.  The modern SharePoint pages are far superior to their classic counterpoints at this point. 

By simply migrating what you have today into SharePoint Online you are starting off with an outdated system and potentially painting yourself into a corner when support for all that classic functionality, InfoPath, and SPD workflows ends.

By taking the time to do a proper deployment planning, you re-architect your site to work with the new flat structure. Look at Hub sites, Teams, PowerApps, Flow… 

2. Refusing to Change the Way Your Employees Work when you should be giving them better ways to do their jobs

I get it. You spent a LOT of time perfecting a system & solution. It works well, users are used to using it, and you don’t want to affect your users’ productivity by making them change the way they work.

However, that solution almost certainly will not work on a modern page in SharePoint Online, and there’s a good chance at least part of it will have to be tweaked to work in SharePoint Online. You can either spend hours and hours trying to make sure your users don’t have to change the way they worked or you can look at the new tools and experiences available to you and create an even better experience for your users.

Yes, they may have to change the way they work. Yes, they will likely grumble at change, but don’t let that stop you from innovating! If you present a user with a better way to work,  they will embrace it! 

Save time… save money… and be better prepared for the future. Don’t try to force SharePoint Online to be something it’s not by insisting it work exactly the same way it did before.

3. Making Decisions for Your Users When You Should Be Determining What They Need

Once you’ve made the wise decision that it’s okay to change the way your employees work, please don’t go off in a dark corner and create a solution without getting input from your employees. Office 365 provides an excellent platform for collaborating with your users to design and create solutions that will meet their needs.  Too often, we see business leaders making decisions for the users and then solutions are created that may take the big picture into account but it misses a lot of minutia for how people actually work, and in the end, you have disgruntled users or you have to go back for a lot more hours to make changes.

Keep the actual users involved and get their feedback. Help them feel like it’s “their” solution and not “yours” and watch the user adoption sky-rocket.  Nothing ensures a successful Office 365 deployment like creating a solution that solves a real-world pain point.

4. Putting up Walls When You Should Be Putting up Fences

The first thing many organizations do when they feel like things can go way out of control is shut down users’ ability to create.  Microsoft Teams is the latest example where this occurs inside Office 365.   Creating a Team creates a SharePoint Site Collection, Office 365 Group, Planner, and more… and out of the box anyone can create a Team.

Before you shut this down, take the time to put some governance in place and retention policies around your Teams. Educate your users and allow them to use the tools you are paying for! As PAIT Group's President, Stephanie Donahue,  likes to say, create fenced in backyards that allow your users to play but keeps them under control. Don’t destroy the collaboration you are trying to build. If you restrict your users from using the tools that you are paying for and have control over, they are going to go and start using Slack, Dropbox, Zoom, and a bunch of other tools that you DON’T have control over.

5. Repeating Your Mistakes of the Past

Finally, don’t look at the move to Office 365 as something you “have” to do… look at it as something you “get” to do. Take this as an opportunity to fix past mistakes you made when you were younger and more foolish and didn’t understand SharePoint. Finally get rid of that old content that no one uses. Create a rich mobile experience without having to hack a masterpage. Don’t write code to solve all your problems because you COULD in SharePoint On-Prem.

Use the right tool for the job. Learn the new skills. Create the digital workplace you’ve always wanted. Let SharePoint be SharePoint, don’t force it to be something it’s not. You’ll find your job will be much easier, your users will be happier, and in the end, you will probably save a lot of time and money because you were wise enough to listen to my advice.

Don’t know how or where to begin? Contact a partner invested in your success.

There’s lots of great companies out there willing to help you get started. We would be  remiss if we didn’t mention our own company PAIT Group. This is what we do every day for customers all over the world. But no matter who you get help from, get help, get guidance, and don’t doom your Office 365 deployment before it event starts.