iserith
Magic Wordsmith
This is one of the things where your behavior as DM determines how your players play like.
If you reward good roleplaying and clever ideas, your players will try their best to come up with something.
Advantage is that it creates more interesting gameplay. Disadvantage is that players that aren't good at this might feel punished.
If you make everything into a dice roll as long as your players describe what they want to accomplish, then players will eventually stop thinking of ideas themselves and just say "I come up with a great idea".
Advantage is that even players who can't do what their PC is supposed to be good at are not disadvantaged. Disadvantage is that the roleplaying gets pretty boring, unless you as the DM, then come up with good ideas for your players (and that turns into you basically dictating what the PCs do which is another disadvantage on top).
My solution to not being good at something is to keep practicing that thing until I am good at it. So I don't accept "I'm not good at X" as an excuse from anybody, barring some kind of unavoidable disability.
The way one gets good at coming up with a cogent goal and approach (which is all that is necessary to play the game) or being entertaining while portraying a character via active roleplaying (which is nice, but not necessary) is doing it, repeatedly, while sometimes making mistakes and learning from them.