I was going to do a post on this in the other thread (the one I started), but I think that has run its course. I'll put my thoughts here. Be forewarned, this is going to be sprawling because it addresses several things and I don't have the time to concisely break out all of these disparate thoughts.
GYGAXIAN SKILLED PLAY VS SKILLED PLAY
Dungeon World absolutely features Skilled Play. But its not Gygaxian Skilled Play. I don't agree with the position that the generic "Skilled Play" shouldn't be a normative nomenclature in our conversations and needs some sort of new term for the same reason that I don't believe (and no one else does so far as I can tell) that GM Force needs to be broken out into separate camps whether the Force undermines a tactical decision, a strategic decision, a thematic decision or some admixture thereof. Skilled Play isn't quite the inverse of this, but its in the neighborhood of doing the inverse work.
I do, however, (a) think it is very useful to identify "the Skilled Play meta" of various TTRPGs (b) and that there are games that, in fact, do not have Skilled Play as a priority at all (these are games where you're either entirely beholden to Force or there is no move-space or action resolution propulsion to control the trajectory of the fiction).
DUNGEON WORLD SKILLED PLAY META AND WIN CONS
@darkbard mentioned several things above. I'm going to mention some more and I'm going to talk about how you trace the through lines of these decisions to Win Cons. I'm going to say up front that Win Cons are not exclusively the capturing of the gamestate "the game is now over and you have won." I mean you can see this in MtG where either (a) you're in a tournament and you have to win multiple games (this is similar to campaign level Win Cons) or (b) "the conceptual Win Con" is proposed before a singular instance of play and yet once it is achieved either (i) the gamestate "the game is over and you have won" is not fully achieved or (b) the "Conceptual Win Con" is not a singularity that ensures play will invariably find its way there (there is still some doubt and on the rare occasion, some opposition Draws/Draws + Gambits find their way out of the "gravity" of that Conceptual Win Con).
To finish that line of thought, "Win Cons" can be:
* The
actual gamestate attainment of having won.
* A
feeling of the surety (even if misplaced) of control over the gamestate's inevitable trajectory toward having won.
* A micro Win Con that establishes the
actual trajectory of having won a tournament (yet the tournament still being in the balance).
So...
Win Cons and Skilled Play in Dungeon World:
1) End of Session. Did play resolve a Bond, did play fulfill Alignment statement, did we discover something new and interesting about the world, did we overcome a notable enemy, did we loot a memorable treasure?
Each of these are micro Win Cons for a session. The aggregate of them (did we affirm most/all of them) is a separate micro Win Con.
2) There are inevitably going to be multiple conflicts in any given session. However, there is going to be a seminal conflict to the session that resonates with a particular player more than others and it is very likely that this will be a universal thing for all participants.
- Did I propel this conflict toward a satisfying conclusion via aggressively and thematically advocating for what I've loaded my PC with (and the game's default thematic loading in the playbooks)?
- Did I play skillfully in that aggressive thematic advocation via (i) managing the fictional positioning so as to open up the move-space for my character and/or one of my allies, (ii) once I opened up the move-space for myself or my allies was I able to marshal the resources and the moves necessary to wrest the trajectory of the conflict from our opposition (which is a combination of "the GM's say" + "the system's say"), and (iii) did I skillfully manage the decision-points (costs and complications, Dangers and Discoveries) inherent to the 7-9 results so that the game of "Spinning Plates" (inherent to DW and PBtA) doesn't "get away from me"?
TLDR - Did my thematic aggression/boldness + management of the fiction to create Team PC "move-space" + resource martialling + 7-9 cost/complication/danger/discovery game of "Spinning Plates" get away from me or do I stay on top of it = the apex volitional force over the outcome of a conflict that was thematically satisfying (whether won or lost or even if terrible losses were incurred such a a treasured Cohort going down...yet going down memorably)?
3) Invariably in many Story Now games (particularly those like DW), a series of paramount goals will emerge from play for each character. Sub everything at the conflict level into this "cross session" goal and you have the same net situation.
4) Loading out the Map with interesting sites that a PC or Team PC wants to explore to experience dangers and discoveries relevant to their playbook and/or the thematic elements they've loaded out their PC with. Further, the continual, aggressive renewal of this process in the course of play (often by making moves that will add them but sometimes by answering GM questions) so that players ensure they control the trajectory of the developing shared fiction.
So these 4 sites of Skilled Play are my thoughts on the subject. I can go over play excerpts myself and extract the through line of Skilled Play to Win Cons, but I'd rather
@darkbard do so (if you have the time). If you don't have the time, I can do it (and my weirdo memory is good enough to cull things with precision so if you need an assist/don't have the time, let me know!).
Conflicts that are on my mind are:
* The Guide Labor Union Fore(wo)man and the oath to your friend.
* Essemer's Simalacram and the savant toymaker.
* The Covington Affair (or Dogs in the Vineyard again...really?).
* Camp 2, the Frost Giant, and the Ancient Blue.
* The Yettis, the Remorhaz, poor Petunia, Saving Porter Baati.
* The Devourer and Dirk the Bold's final embolditudization.
I think if you pulled out a couple of those and talk about how you feel they interacted with all the facets of Win Cons above, that would do some heavy lifting. If you don't have the time/aren't up for it, let me know and I can transcribe the meaty systemitized carrot + aggressive theme advocation + deft move-space handling and resource martialing.
EDITED - I forgot a big part of Skilled Play in Dungeon World. So added.