What can I do to prepare me to get to X (whatever that is for you)? Do you see any areas for improvement? How am I performing against my performance goals? One

What can I do to prepare me to get to X (whatever that is for you)? Do you see any areas for improvement? How am I performing against my performance goals? One on one's are not time to shoot the sh^t. You can do that anytime. A one on one is used to get explicit feedback from your boss, so make it count. You want your boss to know what your goal is and how you are progressing toward the goal; which sets up the conversation for what's going to happen when you make the progress. This is a very transparent way of keeping everyone aligned. If you want a promotion, to hit your bonus target or whatever, there should be no surprises. Use your one on one to you know, a week or two at a time where you are at. It'll help you either get what you want or set the stage for taking your next job elsewhere; no surprises either way.