I am always for the "attempt first, check result" method, in that we tell you our characters' actions, how we do them and combine them with a roll and you reply just how successful that result would be if at all or ignore it if not applicable. Given you're experienced with the rules, I am certain you can interpret intent as well. Thus, if you feel it appropriate, you can adjust the difficulty class in secret and or add advantage for us, applying the effects - and vice versa for making things more difficult. For example, trying to intimidate a thug might be easily done by the character in question based on what they say and do...

We just don't know that part. Only the Dungeon Master does and it feels more true to form for the game that Dungeons and Dragons is, at least much older versions from what I understand.