So I’m thinking back to when I was in the same situation as
@innerdude described in the OP. I had a couple of players who I knew would struggle with the shift from our more traditional minded play consisting mostly of D&D into games that handled things differently.
In my case, I just threw them in the deep end so to speak, by diving right into a new game. I described a couple of the features of play that were most different, and that they’d need to understand in order to play, and then we jumped right in. This was in a game of Blades in the Dark.
We began with character and crew creation. This process in and of itself set some expectations. We came up with a shared history for the characters… what brought them together, friends and enemies they made along the way, and resources they had at their disposal. This helped give them some clear goals and also background elements to flesh out their character ideas.
I know this is something that many games position as required, but that’s often not the case with more trad games. In D&D, and often in other similar games/settings (and I’d include Star Wars among them), players have their own individual ideas of what they want for a character, and often create them in isolation and then bring them to play.
So for my Blades game, that was half the battle right there. The characters were all focused on similar goals and needs, and had a shared sense of purpose. This mostly left the mechanics and play processes as potential obstacles to playing this nee type of game.
For the most part, I just explained that in as straightforward a manner as possible. I never mentioned “narrativist vs. trad play” or anything like that. I just explained things like “you don’t need to declare what items you bring at the start of the Score, just the Load you have, which determines how many items you may have”.
The game also pushes the participants to cut to the action once a Score is determined. I mentioned this and reminded them of it, but I didn’t do so as sternly as I would now. I introduced the idea, let them plan a bit, then pushed for the Engagement Roll (this determines how the Score starts, in a Controlled, Risky, or Desperate position). They hesitated, thinking more planning was needed, so I let them go another couple minutes, then pushed for the roll again.
I made the roll, which came up Risky, and then I described the situation accordingly, using some of the details they had mentioned in their planning. Then I reminded them that they didn’t have to stick to what they’d said (and if I recall correctly, there were some things that were basically ruled out by the situation) and that for the cost of some Stress, they could establish new information via Flashback.
Because the scenario was pretty straightforward, no Flashbacks were used, but otherwise everyone seemed to grasp the game. The ones who struggled a bit were the players steeped in trad play the longest. They also happened to be the players who play the most video games, particularly CRPGs; so I expect their struggle (such as it was) was due to some mixture of these two things. But none struggled too much.
The next Score was slightly more involved, and was one I presented to them. I offered them their choice of two Scores. One player wound up using our first Flashback. For the third Score, I presented them with three options, all shaped by the first two Scores. I slowly expanded the numbers of Scores to kind of get them used to choosing how to proceed. For the fourth Score, I had some options in mind to share, but by then the players were batting around their own ideas for Scores, so we came up with one from their ideas.
And after that, with each session they became more and more comfortable with the game and the expectations of the players and the GM. They became very self directed and started really driving play. Even the most trad-minded of the bunch was comfortable with the differences in play.
So I think, for me, starting off with group character creation was a big part of it. It involves everyone together, so everyone is aware of what you’re doing with your character, how they all connect, and what their collective goals are. I don’t know if this was something done for the game in the OP, but it’s possible that it may have helped… perhaps if the player in question had discussed goals with the group, his focus may not have been on the kind of default “loot to get more stuff so that I’m tougher so I can loot more stuff” cycle that’s kind of ingrained in traditional play.
The next step, of easing folks into new ideas, may not have mattered as much. Based on the description in the OP, I’d say that the player needs to come to conclusions in his own time. So what I’d try to do is introduce opportunities for goals other than loot/gear acquisition. If he doesn’t bite at first, that’s fine, but keep trying. See if he can be steered in the desired direction. Reinforce this with frequent check ins about the meta of play. End every session with “so what worked today” or “what went wrong today” type discussions. Obviously, that’s something that’s already started, but maybe more frequent discussions about broad topics instead of a deep discussion focused on a specific one may help.