Review: Office 365 fails at collaboration

Despite years of promises and gap-filling acquisitions, Microsoft's collaboration toolkit remains a woefully inadequate mishmash

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Shared calendars: Outlook Groups could work, if only it ran on the Mac (and mobile)

For years, many of our staff members have used Google Calendar to share everything from employee absences to industry events. Google Calendar has long made calendar sharing supereasy on desktop browsers, and its integration with the standard iOS and Android mobile calendar apps has meant any user on any device at hand can fully participate.

To use Google Calendar, we must go through a personal account, which makes it hard to manage access (both coming and going). That's against company policy, for good reason.

Exchange calendar sharing via Outlook is often unworkable. Like Google Calendar, Outlook lets you create specific calendars you can then share separately -- if you know where to look. To share a calendar, you have to right-click it, or select it and click the Calendar Permissions button, then modify its sharing permissions globally or for specific users.

Unfortunately, sharing calendars is not easy. We rarely could get it to work with any combination of Macs and PCs; initially, everyone got permissions errors or the occasional app crash when trying to access a calendar shared to them. Microsoft says Mac Outlook users have to share their primary calendar’s folder for others to be able to see their shared calendars.

But taking that extra, unintuitive step only worked for people seeing the calendar in a browser via Outlook Online. You actually have to do more than enable the primary calendar's folder: You have to set the primary calendar's permission to Editor and change the Read setting to None; simply enabling Folder sharing doesn't stick once you save. Then you share the other calendar, the one you meant to share in the first place.

Though we could see shared calendars in Outlook Online or in Outlook for Windows once we did these machinations, we could not get Mac clients to access shared Mac calendars, nor could we get Mac clients to access shared Windows calendars. Once again, Microsoft has hobbled Mac users in Office 365.

Also, it turns out that the sharing settings differ slightly from platform to platform and Outlook version to Outlook version, making user training very difficult. (It's not so easy for IT to keep those differences straight, either.) If they're off in any degree, sharing fails.

Plus, Outlook is inconsistent in sending out invitations to shared calendars. Invitations often were not sent, and those that were sent had XML attachments that Outlook for Mac could not parse, so users could not actually accept the invitations to the shared calendars. The process within Outlook for joining a shared calendar is awkward, unintuitive, and cumbersome (and often didn’t work).

Our IT team's advice: Have IT set up and maintain all shared calendars, given how difficult it is for users to do so themselves. When enterprise vendors make products that are so difficult to use, is it any wonder users adopt unsanctioned tools like Google Calendar instead?

Furthermore, Microsoft’s Outlook client for Android and iOS cannot initiate calendar sharing, nor can it access a calendar that is shared. Neither can the native Calendar clients in iOS and Android. The OWA client in iOS and Android can share your primary calendar as a Web link or .ics file, but not access one shared to you. Apple's OS X Calendar client can access a shared primary calendar, but only in read-only mode, regardless of the sharing setting. OS X Calendar has a tool to share your primary calendar to others, but we could not get it to actually work.

Why would you use a non-Microsoft client on a mobile device? One example: Apple Calendar in OS X and iOS can check attendee availability and even suggest a time that works for everyone. Microsoft’s Outlook app can’t do either.

Outlook Groups is easier to use, but has very little platform support. Again, we looked into using Outlook Groups to share calendars, but Outlook 2016 for Mac doesn't support it. And the Outlook Groups apps for iOS and Android, available only for smartphones, support merely the messaging features. Calendars in Outlook Groups don’t work with Microsoft’s mobile Outlook and OWA apps, or with the native iOS and Android Calendar apps. What you can do in iOS or Android is use the Office Groups app to add a shared calendar to your regular calendar, so it’s visible in other apps. But that defeats the purpose of a shared calendar.

That said, our development and engineering group -- also a mainly-Mac group -- uses Outlook Groups and likes it. This group can get around the lack of native Mac support and poor mobile support because they generally work at their desks, where leaving a browser tab open all day is acceptable. That group’s positive experience gives us hope that one day Outlook Groups will work in our more location-diverse, device-diverse environment.

Unfortunately, in the meantime, the Calendar apps in iOS and Android aren't any better than Outlook Groups when it comes to Exchange calendar sharing. They can see shared calendars you've enabled in your desktop client, but they can't share their own calendars. For now, the only tool that comes close to Google Calendar's sharing capabilities is Apple's iCloud, but that doesn't work in Android or Windows, so it's not a real option either. 

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