Some very interesting food for thought here. Thanks for the comments!
If you're "disinclined to take action" because it won't reward you with XP to roll for a stat that's not highlighted, or because the roll might fail, then you're not playing your character like a real person. Real people don't get to know beforehand what actions will reward them or provide learning experience (okay, "go to college" is usually a pretty safe bet) and they sometimes try to do things when the odds are stacked against them or when it's unquestionably against their immediate best interests.
I get this, and I agree with it, to a point. Here's my take, using AW as a base.
If I want to get something done in AW, I generally have multiple ways to do so. If I want somebody to tell me something, I can go aggro on him, if I'm willing to potentially hurt him. I can manipulate him, if I've got something he wants (like cash, or an offer of sex) or something with which to threaten him. I can read him, and ask, "How could I get your character to tell me what I want to know?" That's three options any character has, always, to get information out of somebody.
Even if I want someone dead, I can either be all sneaky and shoot them with a sniper rifle or stab them from behind (go aggro), or I can take them on, face to face, in a major shootout (seize by force). Normally, they both use the same stat, but they offer different possible results, and there are things that can switch go aggro onto other stats, so the choice is important.
So, I would play my character like a real person. He's a gruff, rough and tumble guy. He's prone to slitting throats. He wants info from Daff. Looks like a go aggro, right? He's willing to kill Daff, even if it means losing the info permanently, so yeah, let's go for it. He's got other options, but go aggro is the one that fits both with what he's best at, and with what he's like. The two go very strongly hand in hand in AW.
But! Someone highlighted my guy's Hot at the beginning of the session. It's a big fat -2, so normally, I'd steer clear of it as a player, and the character would steer clear of it because he knows he's not great at seducing or manipulating. Makes sense, right? He'll manipulate when absolutely necessary to get what he wants, but generally he finds he's much better with the whole "I will kill you if you don't do what I want" approach. But in this case, I choose to have my guy manipulate, purely because someone highlighted my Hot. This means both that I have an incentive to do it (a purely out of character incentive, by the way), and that another player at the table thought, "Hey, it'd be cool if Brendan's guy manipulated or seduced more often this session, instead of knifing people," giving me yet another (OOC) incentive to do it.
In other words, I just made a decision about how my character would react, entirely based on the highlighting. I don't think I just did anything wrong or against the agenda of the game, there. In fact, this is the only purpose I can see behind highlighting. To say, "Hey, do this more often, please!" If players aren't going to try to use highlighted stats more often over non-highlighted stats, then why use highlighting at all? Simply so that you periodically get an XP for what you would've done, anyway?
Okay, but in this case, because of the way DW works, I don't have options. I either talk to the guy using Parley, or I don't talk to the guy at all. I can't read him, I can't go aggro on him, I just have to Parley with him. So, I either use Charisma, or I don't do anything. My Charisma isn't highlighted, so the force of the highlight, which might've tipped me over as a player into using my poor Charisma, isn't there.
So then I default to the question, "Well, what would my character do here to get him to talk?" I know the answer is, "Break his kneecaps, then ankles, then elbows, until he starts talking." Which, I guess, is a Parley? So, I would Parley. But my character also knows that the cleric, bless him, is a great talker. Gets people to do what he wants all the time. And the whole leg breaking thing, well, that works pretty infrequently for Annika (my character), for the out-of-fiction reason that I've got a low Charisma. So, isn't it entirely reasonable for my somewhat amoral, pragmatic character to step to the side, let the cleric do the talking?
Which is great! That's something the cleric made himself good at! He should be rewarded for it. I didn't give myself a high Charisma, it's my own damn fault. Plus, he's got his Charisma highlighted! Even more incentive for him to do it, and for me to let him do it. It all seems good.
Where it starts to bug me is that any time the cleric is around and our agendas align, Annika would always step aside to let him do the talking, with the exception of when my stat is highlighted. Because then, I would specifically say, "Well, I want the XP, so, 'Get out of my way, Cleric-boy! I need to do some leg-breaking!'" (Also, in relation to this, are you saying that if my Charisma was highlighted, and I've established that Annika normally defaults to the cleric doing the talking, then I should still choose not to roll Charisma based on that precedent, instead of choosing to roll it because I want the XP? That doesn't seem terribly fun to me.)
Answers there are: (1) Disharmony: Our agendas should align less often. (2) Separation: The cleric and Annika shouldn't always be together. (3) Just do it: I should try to talk and Parley anyway, even if the cleric is around and my stat isn't highlighted.
(3) just doesn't jibe with me. Doesn't seem to make any sense, either as a player or as a character. (2) would be fine, and (1) would be awesome.
So maybe the answer is that we just need to play more. We need to get more (1) and more (2), so that (3) stops coming up and bugging me. From what I gather, the more you play, the more (1) there is, and in turn, the more (2) there is.
To Sage:
Didn't even think of the difficulties in the more defined D&D stats. I guess there's a part of me that wants to pull the silly move of saying, "Well, you can define them liberally! Strength can mean strength of character, too! Dexterity can mean verbal dexterity! Constitution can mean you're stoic and tough to affect, socially!" But that feels a bit silly, and definitely out of character for D&D. So I get what you're saying, and that makes a lot of sense. The move-switching business may not work as well for DW, except where fictionally appropriate.
That said, I do think I uncovered a bit more of what bothered me in my above response. In AW, I often have 3 or 4 ways of approaching any goal. I don't think I have those options clearly described through moves in DW. If I want someone to tell me something, I have one option in the moves: Parley.
(Side note: Unless the Spout Lore questions can be interpreted more openly? I didn't think this was appropriate, particularly when I was dealing with an assassin of an order I'd never met until that day. But, can I just say, "Aha, I recognize them!", establish that as truth, and then Spout Lore to ask of the assassin, "How can I make it tell me what I want to know?" Is that acceptable?)
So, while my Gunlugger can approach the issue of obtaining information a bunch of ways in the basic moves, my Fighter can't. Admittedly, there are other options outside of the basic moves that I'm not including, such as bribery, or obtaining a truth potion, or whatever. And those are good ideas that I should keep in mind. But when I'm interrogating and threatening a bound assassin, whom I wouldn't bribe, then I'm only going to Parley with him by the moves. I have no incentive to do that as a character because I know I'm not good at convincing people of stuff and the cleric is better at it (after all, I fail at doing it all the time, even when I'm threatening with my badass gigantic bloody hammer named Pain), and as a player because it's not highlighted.
Thought of another way: I'm not sure a stronger person is a more intimidating person. AW gets around this due to the nature of its stats (Hard isn't a physical thing). In DW it seems to me that a wizard threatening with his spell shouldn't be any different than a fighter threatening with his sword, hence using Cha to do it.
That's a very good point, about the fighter and the wizard. Makes a lot of sense. I'm not sure the notion of sloughing responsibility onto Charisma sits well with me, however.
I think, based on a lot of what you said, DW is way more heavily entrenched in D&D tradition than I had expected. And I think what I may be picking up on is that I'm not really that interested in D&D tradition.
To Tristanasaurus-Rex:
We definitely had much less experience in our first session than you describe, and that may be something we just have to talk about/work on. As I said, my Str and Con were highlighted, and we had a single, relatively short fight, so I got a total of 4 xp, I think.
I still don't entirely agree with what you say about XPs. XPs are OOC incentives. I guess the D&D model is more like, "Ah, you killed the monster! Good job! Here's some XP!", and less like, "Well, this game is about killing monsters, so you only earn XPs for that, so go kill monsters if you want XP, which you should!" In other words, more reward than incentive. But I see AW highlighting as being incentive based. So either highlighting works differently for DW, and it should be more reward based (do whatever you would do anyway, and if the right stats are highlighted you'll get a reward), or it's still like AW and is incentive based (you as a player should favor doing these particular things because your stat is highlighted). If it's the former, then that definitely is a shift from AW and my current point of view.
I see what you're saying with Gladiator and interpreting it broadly, but to be honest, it feels a wee bit odd to me to interpret as, "Well, a single person is an audience, right?" I guess it's accurate, but it feels against the spirit of the idea. I mean, it's about being a gladiator! In an arena! Lots of cheering! Noise! Some dude giving you a thumbs up or down! Pennants! Giant foam fingers!
If that loose interpretation is the intent, then Gladiator makes a bit more sense, but it still seems like situations in which one person is specifically watching, and not participating, wouldn't be terribly common. I guess my real problem here is quite simply that the fiction makes me want to take the move, but making my character mechanically awesome makes me want to avoid this move. If you're telling me that I should follow the fiction, then I should take this move...but the fiction also follows the mechanics, and I think that if I want my character to be awesome, then mechanically, I'd be better off with other moves. Even though I love the idea of emphasizing the fact that Annika is an expert pit fighter, she's just as much of an expert pit fighter, mechanically, if she's Merciless. Plus, that'll help her elsewhere, too. Maybe I need to be more willing to say, "I don't need to maximize the character's mechanical efficacy; I should follow the fiction." But this both seems out of character for a D&D style game, and for AW, too.
(Like I said before, if Gladiator were an option at the character's start, instead of, say, Underestimated, then I might feel differently about it. Or if every class got a couple "Background" move possibilities, like "Gladiator," "Mercenary," "Guard," and "Thug" for Fighter, and "Monk," "Preacher," "Wanderer," and "Adviser," for Cleric, just as potential examples, then I could see Gladiator fitting in really well.)
I will be taking into account everything I've been told going forward. Hopefully, we'll (and by we will I mean I will) figure this game out a bit more, get it a bit more in line with its intent, and it'll sing like it has for so many others. I still have a lot of hope. I adored a lot of things in this game (like bonds, for one, and my unique weapon, for another). I do still want to play a lot, and I just wanted to make that clear. Thank you for all the hard work, Sir Sage; it is very much appreciated, despite my whining.