Office 365: Tales from the Trenches

Office 365 has become a passion of mine. I started with only a notion that 365 was a cloud offering of Microsoft products; more than a year later clarity to the underlying products came once my org began transitioning in effort to 365, and getting user feedback.

Here’s my take on some of the good, and yet to be good parts of 365, listed by product.

  • Office 365 Groups
    • Pros:
      • It’s right there in Outlook! For many organizations, a user’s primary interaction with O365 is Exchange Online; so adding a new method to collaborate where users communicate most often makes sense.
      • You can Join or Subscribe to a group in your Inbox: A member of a group can decide whether they want to subscribe to group messages directly in their e-mail Inbox; or keep group e-mail separate and just view them from time to time in the group. You can also leave a group if it’s no longer relevant to you.
      • New members can get up to speed: Unlike a distribution list, a new member to a group can see all the historical conversations prior to their joining the group.
    • Cons:
      • Groups in Outlook isn’t really “Teams-aware”. It would be nice if the format inside the group in Outlook would switch if it’s a Team. I think Teams seems to be a better way to utilize a 365 Group than a group alone. More on Teams later.
      • No Folders: Some users may find the lack of being able to create folders within the O365 group mailbox frustrating.
  • Planner
    • Pros:
      • It’s good for basic task management: Planner shines with Team assignments. It’s worked to put all of a small teams tasks on one page. Members of the plan can add notes, mark progress, and re-arrange tasks.
    • Cons:
      • It still doesn’t do a lot of stuff people want (Recurring “templates”) for buckets that tend to be repeated in an org.
      • Creates a unique O365 Group every time people create a new planner. That makes groups messy.
        • Workaround here is to create multiple planners in Teams, and only the Teams O365 group sticks around, planner won’t create additional O365 groups (I’ve read)
      • No calendar integration across the board, they’re still working on it. iCalendar feature or something, No web calendar view. Needs to mimic Trello features at least.
  • Teams
      • If you create a new team, and Teams creates the group, no users are subscribed to the O365 group, so they won’t see group emails unless they click into groups. This is fixable after the fact with the Set-UnifiedGroupLink command.
    • because you can’t as an admin control the “third party apps” people see… (ie users see “I can use third party app Asana, or Trello in Teams and think that means it’s blessed by the company.. No it isn’t, we’re not paying for the third party product, and it has zero data governance so no don’t use it..)
    • Users are confused by the reply buttons, and that is 100% on microsoft. The bottom “reply” is to start a new conversation, and folks should hit the “reply” button to the conversation that is relevant to their reply. Users, even educated ones don’t get it.
  • Whiteboard
    • We don’t have touch enabled devices for the masses, you have to push some super hidden button to enable drawing by mouse. Not very helpful unless we plan to run it in conference rooms (we might)
  • OneNote
    • You can’t share just an individual “page” in OneNote despite it being a folder/file structure Non-Teams and Groups aware users create a separate “Shared” notebook they then share to users.. (.one Notebooks are pages, folders, sections, blah blah; OneDrive hides that from view but who cares just allow share of a single page in a Notebook, not the entire notebook.)
  • Skype for Business
    • We’re having issues after the Office MSI to Click2Run rip and replace where S4B is not auto starting at startup.. Even with the tickbox in settings checked.. It’s a registry stupidity where the reg key is still pointing to the old MSI Office location (Click2Run creates a subfolder called root now instead of putting Office stuff right in Office16, stupid MS)
  • OneDrive for Business
    • The desktop integration seems to be hit/miss on Windows 10, especially with MFA enabled. I’ve seen it break sync and then you come to expect sync, and find files on your laptop aren’t available to view on your phone.


Review: Office 365 for IT Pros – The Best Book Covering Office 365 Available Today