TL;DR: Do the work to make the plan before soliciting input.

There is a big difference between the boss and the second-in-command. There's a big difference between the Captain of the ship and his First Mate. One of the big differences is a subtle mental change. Sometimes the difference in your mind can be caused by simply changing a few common phrases.

Instead of "Where would you like to go eat dinner tonight?" use "I was thinking that new place, Geppetto's Italian on Longnose would be great for dinner tonight, say 7 O'clock?" The first question requires her to think of all the places that you might go for dinner, and then assess her own feelings. The second lets her simply evaluate her feelings about a particular place. This takes more work on your part. You have to figure out what you're hungry for and where you want to eat before making dinner plans.

Let's say you want to plan a date. Instead of "When would you like to have date night" use "Have you made plans for dinner tonight? I was thinking that new italian place at around 7. Wear something nice." The first one requires her to think about all the things that they have going on in their life. Maybe she has lots of stuff going on, and your question just makes them feel overwhelmed. The second requires that they only think of one thing: tonight. The thought of going out somewhere nice means they're not thinking of all the rest of the crap in their life and trying to organize their busy schedule around you. It's just tonight.

Instead of "Would you please give me a blowjob?" the phrase that came up in a recent post was "I want you to suck my cock." The first one is a question about some upcoming tasks that she may or may not get around to. The second one isn't a question at all, but instead a statement of desire. It gives her an opening as to what would make you feel good, and lets her be feminine in satisfying your needs.

Your mileage may vary, but making the change from asking to telling is a very big one. You have to do the work beforehand to figure out what you want, but it allows her to follow, and naturally puts you in the position to lead.