A reader writes:
I'm a sales rep and we need to make x number of presentations a day. My boss has a looser definition of what a presentation is than his boss does. My boss has given me different direction than his boss has given our department. My boss' direction leaves the integrity of his direction in question. What should I do? Follow the direction of my direct boss or his boss?
This is the kind of question that frustrates me, because I'm baffled about why you don't just ask them about it. It's not just you; lots of people are unsure about how to handle this kind of thing, and I wish people wouldn't agonize over it so much. So often, when you're stumped about how to handle a work situation, the situation is to just be straightforward.
Just say to your boss: "Jane was pretty clear that she wanted us to do ___ instead. I'm hearing different directions from each of you and I'm not sure how to proceed. Could one of us talk to her so that we can all get aligned?"
If he insists his way is correct and you can ignore his boss, say, "I'm a little uneasy ignoring direct instructions from Jane. If you're sure I should, I'd at least like to send her a quick email and explain that we talked about this, so that she doesn't think I'm just ignoring her."
Now, if you have a boss who doesn't handle this conversation well, then your problem isn't conflicting instructions; it's having an inept boss. But barring that, straightforward is the way to go.