Dear Jackass

Dear Confused in the Corporate World:

Let me start my answer with questions. Is this boss a man? I would bet my (jack)ass on it!

What types of questions are you asking him? Are you asking him in person or virtually?
If you are asking for a raise, and he responds with a question–he doesn’t think you deserve one. And even if he thinks you do, he’s worried that will take away from the bottom line and his raise. So that’s a polite “no.”
If you are asking follow-up questions from a meeting–he wasn’t listening, either! He was probably drinking wine from his coffee cup and even blowing on it to look legit. And He was probably wearing nothing below his shirt and tie but some tidy whiteys with skid marks. And maybe some flip flops. Because he has to take the dog out on his leash because a tree fell in the back yard and he’s been too lazy and cheap to get the fence fixed.
If you are asking for time off–he’s thinking of who he can pass your work to if he approves it because he’s certainly not going to do it! He has to walk the dog, you know!
If you are asking him about promotions or positions or anything involving staffing–he doesn’t really care as long as it doesn’t result in him doing more work. And actually, if he thinks he can do less…there goes the hamster wheel.

This situation you speak of reminds me of undergrad. I had this evening class, Grammatical Structures. The professor was a lovely man. He was short and small in stature. He wore a hat that looked like something a train conductor would wear. So, I called him the conductor. A few of my friends were in that class, but otherwise it was a snooze. The textbook was called Doing Grammar. My best friend, Jim and I would always say “do grammar before grammar do you” among other obnoxious things to entertain ourselves. (I wrote my first movie during that class. I was so productive. And bored.) Anyway, this class was a split 400/500 level class. Half the students were in grad school. They were all teachers in their mid to late 50’s. They all worked in the same district and knew each other. It was like a tiny cult. And they did the same irritating bullshit. Every time the professor would say something, one of those assholes would raise their hand then ask him the very thing he just said. Like–weren’t you old fucks listening? Turn up your hearing aids, dickheads! I called them the postmortems. I thought no one besides my friends knew of my nickname for them–only to come to class one day, and none of them were there. The professor came to the back where Jim and I sat and asked me where the postmortems were. I laughed nervously, wondering if he knew he was the conductor.

Back to your dilemma, Confused. The real reason your boss answers questions with more questions is simple. He does this for a few reasons. He wants to confirm he understood you because he wasn’t listening. He wants you to figure it out yourself. And most importantly, he really doesn’t know the answers.!!

The solution to your problem is simple: do whatever the fuck you want and tell him later. It’s better to ask for forgiveness than permission. And if he continues to respond with questions, ask him some extremely personal and uncomfortable questions just to make him squirm a little. Or…respond by asking more questions. Play his game. All day. Because even a salaried employee is paid by the hour.