Failure is a guaranteed part of playing roleplaying games. A lot of systems therefore take steps towards making that failure fun, or count for something. Some try to alleviate harsh, do-or-die consequences, and others even go so far as to award the players for their failed tests. However they do it, it’s what is called ‘failing forward’ or ‘failing up’. The idea is that because the game is a narrative and a shared story, something interesting can come out of failure, rather than an absence of success and dire consequences. It’s all about narrative positioning – does this failure actually spell disaster, or can be it reversed? Would the player prefer to make a deal to succeed now and deal with the fallout later?

Here’s my 3 tips that you can start using immediately to turn your player’s failings into something a lot more interesting.

Don’t make player characters look incompetent

Players will fail their dice rolls, its bound to happen. Sometimes they’ll get a critical fail AKA a natural 1, and there’s this hilarious idea that this means a catastrophic failure takes place. Whilst this is indeed good fun for the other players to observe, the player who failed the roll may not enjoy their cleric, who has considerable skill with a mace (+5 probably), throw it out of this hand and thwack his fellow party member on the head. A natural 1 does not mean that the character is ridiculously incompetent 1/20 of the time.

Instead of forcing your player’s character to be dreadfully incompetent, why not turn it around so the enemy or object of the test is unusually good? It’s like when you lose in a multiplayer game; people are quick to declare you or the team terrible, but it’s much more likely that the enemy was just better or having a better day. Your natural 1 is the enemy having a good day. It’s a drunk falling between you and throwing up when you try to charm that lord. It’s a monster covering it’s tracks because it knows you’re following it.

“Devils Bargain” instead of saying no

So your players are being cheeky and want to push their characters beyond their normal means, or maybe there is a role that they desperately want to make but it sounds impossible. Rules as written is that you could either say simply ‘no’, or, you could set a difficulty rating of 25 or something so that only a near natural 20 could succeed. It’ll mostly end in a disappointing failure though. Here’s the thing: as a DM, you can make it happen, but at the price of some juicy drama. Setbacks, flaws, traps and constraints can make the game more fun, just because getting out of sticky situations is entertaining and satisfying.

So you say: “Alright, you convinced the guard not to raise the alarm, but she says you have to not harm any of the guards, and she’s coming with you to make sure.” The player does the persuasion test without having to roll something insane to make something so unreasonable happen, but there’s a price that comes in the form of a complication. This is what we call a “Devil’s Bargain”.

Don’t roll same thing twice, roll to reduce bad effects

In the previous example, let’s say the player refused the devils bargain, thinking it would make the mission way too complicated and hard. The persuasion check fails, the guard is running and going to start shouting. You ask the player “what do you do?” If the player wants to roll persuasion again, tell them the moment has passed for that to work, the guard is no longer interested in listening to your propositions. What does the player do? Perhaps try intimidate by rolling to grapple them, perhaps simply shooting them with an arrow quickly. The success rate of this test will let them know how much the failure is mitigated. The guard still ran and shouted, but the player can limit how much of the castle hears it.

Either way, consequences are in play now for the failure, but the player can limit it. This is good practice because as I said before, sticky situations are fun, and it’ll stop the players thinking they need to roll 18+ for everything for their characters to meet their lofty expectations. A failure followed by success can be exciting, whereas another failure wouldn’t change the game much. It also rewards quick thinking and heroic actions.

In conclusion, give your players the chance to be the adventurers they have in their minds. Daring players deserve success (with complications), and all players deserve a bad day, but also a chance to rectify. Remember there is no ‘game over’ screen in TTRPGs.