Matt, you needn’t quote me the .65. Believe me, I know there is no good way to ask questions, and there are few prescribed phraseology examples for when you do. Half of what I do at work is ask “Would you like to go up or down 1000 feet for direct of flight/next sector request?” I try and be concise as possible while still offering the pilot their preferences. I could easily just decide for them.

While the original post contains more specific examples to asking questions the point I am trying to communicate is that the frequency shouldn’t be dominated by over the top customer service drawn out at length. It should try and be more to the point. Yes, be polite and courteous, and endeavor to help people learn, by it need not become a standard to have a 5 second question turn into a 45 second monologue. DAL123 would you like 12L or 12R? Short and sweet.

P.S. your .65 is out of date 😂

A lot of the times, like Will was getting at with his list of things to consider, it is a common sense thing. Keep it reasonable, and for the most part a pilot will take a shortcut. I have cleared someone direct MLP from south of ATL at work, and some of them take it, some of them prefer to stay on route (even though a shortcut like that is not super common, I just like doing it because it is a shortcut from South Georgia to Idaho). I usually ask the pilot if they would like a shortcut down line and how far if they do want it. That’s mainly for upper level wind consideration, though.

Don't forget that under VMC or as long as the tower can provide visual between an arrival and a departure, you can provide a "released subject your discretion" release along with any relevant control instructions as well.

Visual separation approved between (departure) and (arrival), (departure) released your discretion.