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What is the worst IT setup you have seen at a company?
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I had a boss at an animation company (so not exactly a hub of IT experts, but still) who I witnessed do the following:
Boot up the computer on her desk, which was a Mac
Once it had booted, she then launched Windows inside a VM inside the Mac
Once booted into that, she then loaded Outlook inside the Windows VM and that was how she checked her email.
As far as I could ascertain, at some point she'd had a Windows PC with Outlook that was all set up how she liked it. The whole office then at some point switched over to Macs for whatever reason and some lunatic had come up with this as a solution so she wouldn't have to learn a new email thing.
When I tried to gently enquire as to why she didn't just install Outlook for Mac I was told I was being unhelpful so I just left it alone lol. But I still think about it sometimes.
I'm not certain that it's still the case but several years ago Outlook for Mac was incapable of handling certain aspects of calendars in public folders shared groups and there was some difficulty with delegation send as.
At the time the best answer I had was for the Mac users to use Outlook as much as possible and then log into webmail when they needed to send us. It's been a few years so I can't help but think it's been fixed by now. Or the very least equally broken on PC.