Pretty straightforward.

I don't like it when someone says, "Know what I'm sayin'" when they haven't said anything at all.

For instance, a while ago I was watching an interview with some rapper who said, "I was going out, you know what I'm sayin'?"

Yes. Yes I do. It was not a complicated sentence. Allow me to break it down for you.

You were going out.

Pretty straightforward I think.

I mean, if he was a thoracic surgeon discussing the latest innovations in thoracic surgery, I might have a problem. For example:

"I have recently uncovered an extreme case of pectus excavatum that lead to a mitral valve prolapse. You know what I'm sayin'?"

No. Absolutely not. Please explain in layman's terms.

Seriously, is it necessary to ask over and over again if your audience knows what you are saying? If you're concerned about your communication skills perhaps you should take a class or have a little more self-esteem. Perhaps if you were more confident in yourself you wouldn't need to ask over and over again.

That was probably the problem. That guy was one of those shy rappers. Those modest rappers you don't hear about! That poor man. I can only imagine how hard it must be for him when he's surrounded by all those other over-confident rappers, struggling to try and communicate, asking over and over again if they know what he's saying.