SakanaSensei
Adventurer
I definitely understand WHY Matt handles this the way he does, but I think I generally lean toward "if the player tells me what they want to do and it makes sense in the fiction, I'm going to let them succeed and move on." I think that generally makes things more fun, and I think my players agree generally, though I have had once or twice where a player is doing well in a social situation and they'll ask me "so can I roll Persuasion or something?" and I'm just like, "my guy, you're already succeeding? Why bring dice into it?"No matter how good a plan is, it can still fall victim to bad luck.
I think sometimes people just wanna roll dice because click clack makes brain go brr, which is totally valid.