Deploying Office 365 Pro Plus

There’s a history in IT deployments that they don’t traditionally go well. We’re living in a different age I believe where IT professionals are also becoming good communicators and I believe this has always been the biggest weakness of ours. If you’ve ever watched the IT crowd from around 2010, you’ll notice one thing. These guys are not good with people, they like to stay in their basement and have to deal with people as little as possible. I believe this to be a commentary of IT in general at the time.

Times have changed and the IT professionals that survived now understand that they have to support the business. Every tool, every trick they use has to have a positive bottom line for the business whether that’s critical system backups or the LOB application that they company thrives on. With the cloud, things are better. Gone are the days of improperly configured or resource starved applications. With Microsoft and other providers providing the backend hardware and tenanted systems such as Exchange and CRM, the systems are setup with a standard that always has enough resources and they’ve left the customization and unique configurations of those systems to your business.

The one place we need to plan and communicate extremely well though is deployment day and you need to go into that period knowing that the end user doesn’t necessarily care about the technology the same way you do. They don’t get starry eyed about the feature they may never use but they will be extremely happy with you if you can make their life easier.

When deploying Office 365, you have to consider that the collaboration features available that can fundamentally change the way your employees and colleagues work together. You might have some pieces already working in your datacenter such as SharePoint and Exchange but Office 365 adds a whole host of features and one of them is the ability to always have the latest version of Office 365 Pro Plus which is essentially what we’ve known to be Office 2016 and its iterative versions through the years.

Microsoft has provided a website to help consultants and administrators be successful with Office 365 deployments. The Site is called the Office 365 Pro Plus Deployment Portal and it offers some entertaining videos that illustrate how people feel when good/bad deployments go, where I found the most value was in Preferred Practices for Office 365 Pro Plus deployment. Here they offer

  • Customer Scenarios
  • Preferred Practices
  • Methodologies for Deployment

They break the deployment out into 5 steps, and break each out even further.


For example when you’re dealing with the Assess section, you’re going to be look at things like Environment Assessment and Application Compatibility Assessment to ensure you aren’t just rushing into things and not considering the implications of just throwing new software into the field.

They have an outline you can follow through the different phases.


I especially like the Call to Action section that gives you access to a questionnaire that will help guide your assessment.

In a second part, the Planning Phase, they consider things like allow the N-1 coexistence scenario where you can go back one version and have both running side by side and the implications surrounding that as well as the introduction to the Office Scrub Tool which will help clean legacy version of Office to ensure there no past bugs that will affect your performance. They also have a section that talks about packaging and deploying Office for Mac since Mac’s are becoming a considerably favorable platform to employees.

One other extremely useful resource that I can’t say enough about is the deployment section. This is where the meat of your project will be, here is where you will know once this is done if your project will succeed. You can communicate as much as you want, but at the end of the day if you can’t deploy properly or have proper instructions for deploying all of your communications will fall by the wayside. In this section Microsoft offers advice on

  • the three common deployment options (Enterprise Managed, Locally Managed, Cloud Managed) which basically refer to how and where you are deploying Office 365 Pro Plus from.
  • Source File Distribtuion Locations (Local source path deployments vs. Off Premises using the Office CDN)
  • Office Deployment Tool

Here is an example of some of the deployment content you might find here


The last two sections focus on Managing and Reference Material. They are also useful and talk about how to manage updates, how updates work with Office 365 Pro Plus. The Reference Material page gives you access to a bunch of videos that will help you through your Office 365 deployment.


I would am spending a bunch of time in this portal absorbing as much information as I can because I too want to the be the IT superhero to my company.


  1. Very timely! 35 user deployment with 10 on RDS this weekend – thanks for doing a bunch of my research 🙂

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