Player: “I want to pick the lock!”
DM: “Okay, go ahead and make a thieves’ tools check.”
Player: This’ll be easy … I have a +13 to thieves’ tools! I eat locks for BREAKFAST!
DM: Decent lock, so maybe DC 15. Player’s super good at lock picking though so shouldn’t be an issue. Easy for them, hard for others, etc.
Player: Rolls a 1.
One of the problems with a d20 system is that, every now and then, an absolute virtuoso at something will just fail HARD.
Picking an easy lock and roll a nat 1? Tough cookies, Houdini. Doesn’t matter if you could do it in your sleep. You just failed.
It’s really frustrating when that happens as a player. Your character might be frustrated because they failed, but you, the player, are frustrated because you know it had nothing to do with you and was just pure bad luck.
As a DM, there are two things we can do to alleviate that frustration. The first is to just not call for a check at all and assume the player passes, like a passive ability score. Effective, if boring. The only thing people like more than rolling dice is rolling dice, adding a sweet bonus to it, and happily announcing a number up in the 30s.
The other option is to make failure not necessarily mean failure. Nat 1 on a lock picking? Maybe the lock opens just fine but you made a lot of noise. Or maybe your picks break and you’ll be rolling thieves tools checks with disadvantage until you fix or replace them.
Basically, instead of thinking of a normally easy skill check as a binary pass/fail, think of it as a complications check.
Failure can mean just failure, but it doesn’t have to. It’s your game, after all.
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