1. The worst brand management this side of 1984. "Skype for Business" has nothing to do with Skype and the .exe is still called "lync.exe"
2. SDK: Trying to use the C# SDK for even simple tasks leaves your app deadlocking or spinning 100% CPU in threads you didn't create or throwing native exceptions that doesn't make any sense as they are referencing raw hex 0x12345678 pointers or COM objects you never even touched. And if you try to watchdog all that have fun with 5 orphaned lync.exe's claiming your USB audio/video device.
SharePoint's virtual path for its SOAP services is "_vti_bin". VTI = Vermeer Technologies Incorporated, the makers of FrontPage and the FrontPage Server Extensions.
Then there was Groove (brought in Ray Ozzie's luggage) that was renamed SharePoint Workspace (groove.exe).
SharePoint Designer (which didn't actually have a visual designer in the 2013, and final, release) crashes when performing some operations in source files ... With an exception in the FPEDITAX.DLL (FrontPage Editor ActiveX).
Those can all almost be forgiven - they are like vestigial organs after each product evolved into something else.
Until you get to OneDrive. smh
If it wasn't such a huge PITA to find a compatible SIP library, or write one from scratch, I'd have dumped it long ago. Sadly, I've had to do enough with it that I'm probably an "expert" at it now...
I think this explains a lot of poorly designed but complex enterprise software (e.g. MS). People eventually learn to deal -> poor design becomes less of a pain point -> less incentive to fix issues.
Slack? I use it, but I don't see the attraction. It's just another chat client with a couple of cute features. I'm really not clear on why the world seems so enamored with something that's really not much of an improvement on something we had in 1995.
Saying that Slack is "just another chat client" is sort of like all the old arguments about how much more powerful PCs were than Macs because they have more features—it's ignoring the value of design and conceptual elegance, and the real impact that has on UX and productivity.