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"You are one of those people who say NO all the time. No, we can’t write our own operating system! No, we can’t have a backup of everything! People hate that! You impede progress!"

Now I find myself wondering, why would he want them to write their own operating system

...no. no you don't want to know.

I bet it was one of those insane "I was reading in a management journal about writing operating systems and..." kinds of stories.

whereisbob is the new DailyWTF... I feel like I just hate a lot of empty calories.
And it didn't even have a technical twist. Just whining about vagueness from a boss. So what?
"Bob’s initiatives, literally reeking with an overwhelming stench of incompetence, were consistent only in their absolute absurdity."

I, for one, would love to know how an initiative can "literally reek" of anything.

Ironically, one of the definitions of 'literally' is 'figuratively.'

Go figure.

Sounds pretty straightforward - he wants backups of all server content and he wants to have them maintained not overwritten.

If this was a problem explain why. I can only imagine resources being the problem. If the servers were particularly large you may need to explain that some sectors would take longer to backup.