In my first sesssion I went with a notebook ad the DW book in an iPad, told themt eh classes and they picked, then I went to questions, the most important part here is to ask about their characters first, who are they, what brought them to the point in life they are at the start of the game, where they learned whatever it is that they do, how old are they, and so on, with that you will have them develop the characters, you can then end asking them what they are doing there or hold the carrot to them, using the adventure's central idea adapted to what the characters would want.
I think you are loosing a crucial part, establishing who the characters are, their stories, attitudes toward life and desires. An example on how my character process started with the players:
Classes: Warlock, Fighter, Druid and Wizard.
First question asked after they chose how they look and their names:
Warlock, WHY did you make a pact with the demon?
To gain power.
Ok, what does your pact state you gave to the demon, and I am thinking your soul is there, and what does your demon require of you (check your sheet, it is right there in the Contract move.
I did not sell my soul, I made a pact to gain power in exchange for bringing the demon a lot of souls, my soul is forfeit to the demon if I don't get the number of souls I promised.
Another player asked: HOW MANY souls does your contract asks for? (I grin)
I don't know, a lot, how about 999? (I grin again and accept it.
This revolved around a single move of the Warlock class and its basic premise, "you have a deal with a demon". I asked a lot more questions, but with those alone I already knew he wasn't looking to solve the pact in-game, he also was willing to corrupt others (tied to his evil alignment), and demons and souls would be part of the game.
Hope it helps shed some light.