I used to always try for the best outcome but with this have it seems like half of the time a failure also leads to an amazing consequence and story.
Like this from act one in the Underdark:
spoiler
I had to find a hidden gnome that could supply me with gunpowder, but she was so much on edge that she lit up the barrel of gunpowder and blew up the whole room, leaving half of my party dead. A suicide gnome bomber. I couldn’t convince her that I was not an enemy. Reloaded just to see if I could successfully do it, but much preferred the first outcome of the dice roll, so had to reload and try 6 times until I failed again. What a game!
For dialog & ability checks, I feel like failing is part of character design, and if I’ve chosen to sacrifice charisma for constitution, then I should play the low CHA path. There’s always revivify, but I have scummed over real death. Sometimes, I’d look up the game consequences of success/failure, and it’s never game-breaking. For all the ‘choices have consequences’ talk, you still have to be able to finish the game. That said, years of RPG experience has taught me to always have a max CHA talker and a max DEX lockpicker.