Review: Office 365 fails at collaboration

Messaging: None of Microsoft's three chat tools work well

Microsoft offers three messaging tools, none of which works with the other, but all of which are available in Office 365: Yammer, Skype for Business/Lync, and Outlook Groups.

Yammer works poorly everywhere. We've had Yammer available to us for nearly three years. After all that time, it remains rarely used, and when it is used no one is listening. But we decided to give it a fresh test, in case old assessments were no longer valid. Unfortunately, our conclusions didn't change after that fresh use.

There are many reasons why Yammer is an unworkable choice for our instant messaging. Here are the main ones:

There's no desktop client for Windows or Mac, so you don't know you have a new message. Even if you leave a browser tab parked on Yammer, you have to periodically switch to it to see if anything has happened -- there's no integration with the operating system's notification service. As a result, people forget to check. You end up getting an email digest long after any conversation would have occurred, or needing to set up groups to mail you each time a new message comes in, which means you might as well use email.

There is a tool for Windows called Notifier that lets you know there's a new message in Yammer, but it won't open it for you. Notifier is a mean prank.

There are mobile clients for Yammer that notify you of new messages, but unless you want to issue everyone a mobile device to check for new messages, that's a poor substitute for native notifications. (If you require employees to use their personal devices to monitor corporate chats, be prepared for a legal fight.)

Yammer can barely do live chats, where you can see the conversation as it unfolds. Its live-chat function works only on desktop browsers, though few of our staff members figured out how to do it, because the controls are unintuitive: You click a person's name from an existing conversation to initiate a live chat.

When you close the live-chat window you can't go back to that conversation -- it's gone, unlike in competing tools. Well, you can see that conversation in the mobile app, oddly enough. You can also see that conversation in a folder in Outlook, but not in the desktop browser that Yammer expects you to use. What a mess.

Furthermore, Yammer doesn't have live chats for open rooms, where people can drop by uninvited. These open groups support only the threaded conversation view that works like email.

Yammer is much more about sending messages to preset groups, not so much for ad hoc messaging. Competitors like Atlassian's HipChat and Slack do a much better job of supporting one-on-one, private group, and public group chats -- the whole set of likely conversation modes -- and they do so both via good native clients on all major platforms and via a very good Web client. Yammer feels like it came from a different century.

Still, Yammer works for some other groups at our parent company. The key factors are that these groups are all on Windows and are all deskbound, so they can and do leave a browser tab open with Yammer all day that they can glance at as needed.

Outlook Groups treats chats as email threads. You could use Outlook Groups for such live chats, except the chat occurs in your email, the last place anyone wants to do instant messaging. Plus, an Outlook Groups chat is not at all part of the Yammer stream. Further, because Outlook Groups doesn't work on the Mac, it's not an option for us.

Chat in Skype for Business/Lync is really about supplementing the online meeting. Skype for Business/Lync can do limited messaging, in the way any online meeting tool can for current participants. But if a person is offline, you can't message them and know they'll get it later -- they won't.

So, Skype for Business/Lync isn't really a chat tool, even if it might appear to be one.

HipChat and Slack are much better messaging systems. Both HipChat and Slack understand instant messaging in all its forms. You can have public rooms, private groups, and direct conversations. You can get notifications on all supported platforms' native clients (OS X, iOS, Windows, Android, and even Windows Phone), as well as on a browser. Those clients work nicely and consistently on all the platforms -- unlike Yammer or Outlook Groups.

In both HipChat and Slack, you can create groups from any client, not only the browser. Moving among groups is easy as well. And both let you name-check people to include them in a message session they're not currently in (similar to Twitter's @mention feature). Plus, both let you share links and, through optional integration with various cloud services, documents. 

In our tests, we preferred Slack over HipChat, though we'd be happy with either. Slack's advantages include the following:

• It lets you set separate notifications preferences for individual conversations and groups.
• It lets you use the same email address in multiple Slack accounts to be able to switch among them as needed using a common identity (great when working across departments or companies, or if you are a contractor with multiple clients).
• It lets you more easily move among conversations and groups in the native clients than HipChat allows. (HipChat is clearly designed with the notion of the browser been the primary conduit, whereas Slack considers all clients equal citizens.)
• It presents chat sessions speedily (HipChat sometimes lagged when used on native clients).
• It simplifies onboarding by letting people with specified email domains self-enroll, and it can restrict specified users to specific chat groups.

Tools like HipChat and Slack also let you add outsiders to your messaging. That's handy if you work with contractors, whom you can invite if you choose. Office 365 assumes that all participants are internal, but Yammer users can create what's called an external network, then enroll outsiders into it manually.

Of course, inviting outsiders has risks, especially for a messaging platform with lots of open rooms. Slack offers a paid version ($80 per year per user) that lets you restrict specified users (internal or external) to certain discussion groups. With its paid version ($24 per user per year), HipChat lets you invite outsiders to specific groups, restricting their access to the browser, and showing only the current session -- that's too restrictive for handling regular outsiders like contractors, though.