So I have a very good relationship with the executives at our company. I am not in management, nor am I in a salaried position. The CEO (owner) loves to make his employees happy, but is a bit disconnected from the daily goings on of the hourly employees.
Now I am in an analytical role, and was chatting with the CEO, as we occasionally do, or if he has any questions. I'm looking to go to a work from home model, and passed it on to my boss, with not really much of a reaction ("We'll see"). He's a pretty easygoing guy, and although my boss has thoroughly completely, these are things the CEO has direct control of.
Being the underhanded miscreant I am, the subject came to housing (looking to buy a house, and we struck up a conversation). We began talking areas and I accidentally let slip that if we had the old office or I had the ability to work from home, it would greatly increase my home search area. He laughed and said yeah, it would.
Is dropping not-so-subtle hints about things like that frowned upon if it comes up naturally in conversation or is this a tactic commonly used to get what you're looking for in a job?
I'm not trying to go over my boss' head or anything, but I'm genuinely curious if this sort of thing is frowned upon.