Insider Tips for Office 365

So Good, It’s Almost Criminal

Lane Shelton

Effective communicators know when to speak, and when to sit quietly and let others speak. Here is an instance where I was ready to listen. I asked an enterprise customer (who also happens to be an Office 365 (O365) pioneer) for advice. I was truly looking for some insights from someone with experience about deploying and managing Office 365. And we offer our thanks, for permission to pass along this incredibly valuable, practical advice. Here’s everything you need to know about O365 from someone who’s been there and done that, more than once.

This is truly an inside track on O365. So here it is word for word. I expect you will be glued to your screen.

  • Do your homework: fully evaluate and plan to be in O365 for the LONG TERM. I wouldn’t recommend these services as a stop gap or short term, but also have an exit strategy drafted, and keep up with competitors offerings to help negotiate with Microsoft.
  • Where possible, do a real-world Proof of Concept (POC) rather than an evaluation. This can be challenging if you are planning on using single sign-on, etc. – but it’s worth the investment upfront if you are serious about moving to the cloud services. Work through a well-planned POC to identify any shortcomings or workarounds that will be needed specific to your business. If you are not going to accept the out of the box usage model designed by Microsoft, this will help expose where customizations or configuration limits may impact you.
  • When you’re transitioning, expect the unexpected. Depending on how those services are designed and being consumed within your business today, you may find migration to be more complex and/or less transparent to your users than expected. In our experience migrating the more standard users first over a period of time, using that experience to optimize the process, and then taking a big bang approach to move the more complex users worked well.
  • Make sure you have your cloud vantage support in place and work with them to setup an oversight process to manage the issues/tickets – expect to modify your internal support processes to accommodate these external services.
  • For migration of Exchange, make sure Microsoft provides cost free temporary licenses to move shared mailboxes. Although Microsoft doesn’t change a subscription license for Shared mailboxes, these are needed for the migration.
  • Migrating users to Exchange 2010 on premise (if coming from Exchange 2003) before migration to O365 will help prevent any downtime to your users and enable high velocity migration by syncing the users’ mailboxes while they work. Then cutting them over to the new mailbox (over a weekend) only requires a small final sync, massively reducing the time needed.
  • Staff up your helpdesk to handle the extra calls. Shared mailbox and calendar configurations are likely to impact users; where possible build an effective communication plan so the end-user knows how to ‘fix’ those when/if the migration breaks it in Outlook.
  • Make sure you have someone with PowerShell skills. Currently the UI is still aimed at the IT pro and needs PS to be able to pull in reporting data, etc.

The bottom line?

Would I still recommend O365 after going through a large migration? Yes, but ultimately each company will need to understand the benefits as it applies to their needs and internal capabilities.

This is the raw, sometimes hard to hear stuff about software that we don’t always get these days. I hope you found this unedited advice, absent of any marketing hype as intriguing as I did.

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