Office 365 readiness assessment

A high level summary of considerations for an O365 solution design and transition plan

Okay, you have the green light and it's time to get cracking deploying Office 365. Before a mailbox can be migrated, before even an account can be AADSync'ed, before you even provision the O365 tenant, there is the matter of checking if the existing infrastructure is ready to handle the great features of Office 365.

What is always recommended before the design phase of a project even starts is to conduct an Office 365 readiness assessment. Working on a project recently and having it fresh in my mind, I thought I'd put finger to keyboard (pen to paper) and jot down the key items to check.

There's allot of IT companies out there who offer this discovery and assessment process which is great. As a handy reference point, here's the approach I take, with the a focus on Exchange Online messaging as that's what I'm pretty good at…

Before you start

Sidebar: Office 365 Identity


Directory Services

Identity Management

Exchange Organization


Security Considerations


A couple links to some interesting reads that might be of use:

Additional Services

These are most of the considerations related to the Office 365, more focused on the Exchange Online side. SharePoint Online and Lync Online have their own additional requirements and additional readiness assessment tasks on top of the above.

However, with the complexity that can be SharePoint Server, oftentimes using a third party tool like Share-Gate achieves the desired results with considerable less stress. The only hurdle is procurement of licensing for Share-Gate.

Finally, there is an overview of any Skype for Business infrastructure on-premises and extending that to the cloud, as well as understanding any social requirements to provision Yammer Enterprise.

Microsoft 365 Exchange Online SharePoint Online Skype for Business Yammer

Discussion 💬

Follow or start a discussion for this blog (Office 365 readiness assessment) on Twitter. If you're after something more in depth, or want to ask me an expanded question: raise an issue in my open GitHub AMA repo.