Want Your Games To Be More Engaging? Then Make Failing Interesting

When we roll the dice, there is always that moment of tension. The knowledge that there is a 20 on that die, but there's also a 1. Even if you built your character to accomplish this specific task, and they're properly equipped, there is always that ever-looming specter of failure. That chance that this time, all your planning just won't cut it. But you roll the die anyway.

All right you little bastards... don't let me down...

When you succeed, the very act of success is the reward. You hit the monster, you pick the lock, you sniff out the lie, etc., etc. When you fail, though, it can sting. Not just because you failed to do the thing in the first place, but because of how you can feel dismissed when you fail. You feel like the actions you took were wasted, or didn't matter. The sort of stuff that, if this were a movie, would get chopped out of the final reel, and left on the cutting room floor because it's not dramatic enough.

That isn't a feature, though, it's a flaw. Unfortunately, it falls squarely into the DM's wheelhouse to fix it.

Make Failing Affect The World As Surely As Success

I mentioned back in How To Keep A Positive Attitude At The Table (Even When You're Rolling 1's), that one of the biggest reasons players disengage is a good run of bad luck. Even if you're chomping at the bit to play, all it takes is four or five rounds of unbroken failure for that enthusiasm to drain out of you. Another three or four rounds of doing nothing, and you unplug from the game until something changes. And the reason is fairly simple. When you succeed, you have a narration to make. You talk about how you Fonzie-open the locked door because of how high you rolled, or how your feint followed by a crushing blow to the werewolf's skull lays it low. When you fail, the only impact is that you failed.

Or is it?

Yes, I'm getting to the point.

The primary reason we are uninterested in spending description time on acts that fail is that they have not affected the game world in a meaningful way. Sometimes your grip slips due to a bad Climb check, and you fall, or you botch a Disable Device check, and your lock pick breaks, but other than that all a failure does is whiff.

But what if your failures led to interesting developments in the same way your successes did?

The key word there is development, not punishment. One of the most common things DMs do to make failing matter more is to add penalties. Warriors drop their weapons, spells that don't penetrate SR cause a backlash and do subdual damage to the caster, etc. That's just adding insult to injury, though. The player already failed in what they set out to do, and they shouldn't be punished for that failure with further negatives.

Instead, ask what happens as a result of their failure.

So, the archer took their shot, and missed. And, following the rule of, "don't punish people for trying," we aren't going to have that arrow randomly plant into one of the fighters in the fray. But what else could we have it do? Well, let's say it flew true, but the enemy ducked to avoid a sword swing, so the arrow flew past them. Where does it go? Does it plant itself solidly in a nearby tree? Does it slam into the castle keep's door, shuddering with the force of the shot? Does it hit one of the torches, slamming it out of its sconce, and knocking it onto the floor? Does the torch set the carpet ablaze, creating a fire hazard? Does it instead go out, dimming the light in the room by one step?

Little changes can make a big difference, and if those changes can be caused by failed rolls then players will learn to wait for the results of their actions. Instead of just grunting, and making a hand gesture that their turn was wasted, players will get into a rhythm of adding up the full amount for their action, and giving it to the DM to see what happened. Because sure, they might not have made the DC 30 Perception check to find the hidden door, but their 25 may have drawn their attention to a painting whose eyes appear to be holes leading to the hidden hallway. And while their Use Magic Device check of 15 is nowhere near the necessary DC, the sword they're holding might demand that the PC unhand it, and give it to a worthier bearer, revealing that it's intelligent even if the character knows nothing else about it.

It's important to establish a back and forth with all your players, instead of just those with good numbers. It keeps everyone involved, and interested in what's going to happen next.

Long-Term Planning, Short-Term Improvising

Sometimes making failing interesting is a small thing that happens in the moment. Knocking the light down by shooting a torch out by accident, for instance. But sometimes there are going to be checks that will be more of a long-game. Checks to make allies, for instance, or to catch someone in a lie. Things that will set events in motion. While you should want your players to succeed on those, too, it's important to make sure that if they don't, you still have something interesting planned for them.

For instance, say your party is trying to ferret out a spy at the duke's latest social gathering. They're watching for subtle body language cues, and trying to slip pointed questions into conversation in order to get a sense of who is lying to them, and who is trying to cover something up. Now, as the DM, you know that the real spy is the duke's cousin Reginald. He's handsome, charming, and he's secretly reading the duke's correspondence with the king before passing it along to his masters. However, none of the party members interact with him for very long, and those who do don't make the DC 25 Sense Motive check to get a sense that there's something wrong.

But is anyone else there trying to hide something?

I'm telling you, it's the Countess. There's just something about her...

For example, the players might notice that the head scullery boy is nervous, even though he's trying to appear friendly, and cool. If they grab him, and haul him behind the house for interrogation, they might find that, rather than being a spy, he's been sleeping with the duchess behind his lord's back, and is terrified that he sent you to kill him for it. Maybe the mayor starts sweating a little harder than he should, but it turns out that he's embezzling funds from his office, rather than spying for another kingdom. Perhaps the young viscount really is keeping a secret, but that secret is that he's obsessed with the party's sorcerer, and he doesn't want anyone finding out his true feelings.

Now, the party technically failed, in that they didn't locate the spy. But that failure wasn't just a Game Over screen for not finding the actual spy. They still did something, even if it wasn't what they were trying to do. And it's possible that any of the paths they ended up pursuing might lead them to the real spy... with another Diplomacy or Intimidate check to coerce the suspicions out of the mayor, or to hear from the scullery boy that he's seen Reginald skulking about late at night when the rest of the house was asleep. Or, perhaps, Reginald himself invites them to an after-party, whereby they're ambushed, and they then have to fight their way free to inform their bosses they've located the spy after all.

That's essentially the goal of the DM who wants to make failing interesting on a long-game scale. While there are checks that will get the party closer to their set goals, narrate all their attempts equally, and have events happen as a result of those failures. A bad Bluff check might mean the guard captain knows the party is lying to him, but he may not be sure why. So he lets them go, but with a tail of his own men to spy on them. This could mean the guards are near to hand if the party gets ambushed, or if they try to do something highly illegal before shaking off their tail. A failed Diplomacy check to gather information might get the party something that's rumor rather than fact, leading them to the wrong dock front warehouse. This one doesn't have the cult, or the idol, they seek... but there is a booming brothel on the second floor. And, perhaps, there are some folks there who know about the cult, and can help the party re-orient their course.

If most actions taken (success or failure) go somewhere, then your players are going to pay much closer attention. And while you shouldn't struggle to make something interesting happen every, single time the numbers just don't add up, get into the habit of planning and improvising what happens when they're close, not so close, or completely off-target. It will transform the flow of your game, I will testify to that.

That's all for this week's Moon Pope Monday installment. Sorry it ran a bit long, but it's a topic I've been thinking on for a while now. If you're looking for more content from yours truly, then check my archive over on Gamers. It's full of great stuff, and there are plenty of other talented writers there, too. If you want to stay up-to-date on all my latest releases, then follow me on Facebook, Tumblr, and Twitter. Lastly, if you want to help support Improved Initiative, head over to The Literary Mercenary's Patreon page to leave a little change in my jar. If you pledge at least $1 a month, I'll send you some sweet gaming swag as a thank you!