I mentioned in a management meeting recently that I needed to ask one of the folk at Head Office whether he could help us advertise one of our initiatives. My boss' response was, 'While you're at it, can you ask him whether he's yet managed to talk to Bill about funding for the XYZ project?'
Seemed a bit convoluted (Tim: my boss has asked me to ask you whether you have yet spoken to Bill about XYZ...), but I did as I was asked. I then forwarded the response to my boss when it arrived and he immediately emailed me back saying, 'Can you ask Tim if I can phone him about this before 11am on Monday?'
What's the point of that?? By the time my boss had asked me to ask, he may as well have asked Tim directly if he could phone him, thereby saving everyone time. Plus, it looks pretty stupid me saying 'Tim: my boss has read your email and has asked me to ask you whether he can phone you before 11am on Monday.'
But I did as I was asked. Not much choice when it's your boss, really. Still, I do sometimes wonder at the oddities of senior management....