Believe it or not but our IT department consisted of two sys admins, six helpdesk chaps and four managers of various flavours as a result of business mergers. We could have done without the managers, mine in particular, though I do now have a lifetime's worth of work anecdotes.
Curiously enough the company did go bust shortly after most of us escaped, something we found hilarious. The VLAN argument was in regard to QOS on VOIP services because "we'll be fine without VLANs" didn't seem a sustainable policy to me.
There was the day he wanted to move servers at one site to another site (and subnet), just because, and asked if we'd need to change the IP addresses on them or if they'd just work.
Or the day we had a flood of spam that was traced back to one of the directors complaining that an email had been blocked and our glorious leader turning off most of the filters instead of just releasing it.
I could go on :(
The truly distressing thing was the fact that the directors seemed to think the sun shone from The Ass despite his obvious lack of, well, everything. Boggles the mind really.