I think I've been jumping the gun too quickly when it comes to "helping people figure things out". To reiterate: it's much better to have people figure things out for themselves, rather than telling them. I think I've been rather aggressively telling people things, rather than letting them make mistakes. Mostly in the context of board games, where I try to figure out what's optimal for them, and then helpfully tell them.
It's probably not actually very helpful. Also, takes away from the fun. Something about how it's good to let other people make mistakes they can afford to make.
But also, more board-game-specifically: when I'm showing other players a new game, how well should I play? It doesn't seem very conducive to the other person's experience if I try Very Hard To Win. And it seems good to let the other person get a feel for the game first.
This seems harder in games where I can't just "play a weaker deck", or whatever the analogue is.