Regardless of the nature of a challenge–trap, hazard, skill check, etc.–try to structure them so that the hero or heroes have multiple chances to beat a hard difficulty. Don’t structure them so that they have multiple chances to fail an easy difficulty. Here’s why.

Multiple Tries

If the hero has a 25% chance of failing the roll (difficulty 6 on a 1d20) but has to roll four times, there’s a very good chance (about 70%) that one of those rolls will be a failure. You thought you were making it pretty easy, but you actually made it very hard.

On the other hand, if the hero has only a 25% chance of success (difficulty 16 on a 1d20) but gets four tries at it, there’s a very good chance the character will succeed (again, about 70%). Not only did you accomplish what you actually wanted, but you get multiple degrees of success. Depending on how many rolls it took to succeed, the character did:

1. Very well
2. Pretty well
3. Okay with some difficulty
4. Really struggled (or took a long time, etc.).

Eventually beating a high difficulty also feels better than not missing multiple easy rolls. If the heroes each have just a 10% chance of success (19 or 20 on a 1d20) but there are five of them, then together they have a roughly 50% chance that one will succeed. Or give them more chances but only a natural 20 will do.

• Cheers go up as the halfling’s second throw lands a rock squarely in the trap mechanism, halting its grinding descent and whirling blades. “We needed a natural 20, and I only had a couple of chances, but I got it!” the player will tell friends later, forgetting that the other players also rolled and that he actually had two more rocks left.

You might use this method for crossing a dangerous river.

• The heroes can make strength or dexterity checks to make progress–four successes each allow you to reach the opposite shore. A failure means you make no progress for the round. A natural 1 means you lose your footing and get swept downriver, where you’ll have another challenge to avoid drowning (significantly tougher in armor).

Roll Fast

This also works other ways, such as allowing the players to roll as many times as they want within a certain time limit. You could simulate a horse race by letting the players roll as fast as they can to collect two or three natural 20s or else boxcars on 2d6 (a 1-in-36 chance each).

Or maybe a footrace could have each player rolling to collect natural 1s, but the die they roll depends on their combined constitution and dexterity. So a very fit character might roll a d4 while a weenie might roll a d10. (Or use d20s, and the guy with +3 for CON and DEX only needs a 17+, while the weenie needs a natural 20.)

Steady Progress

Another way to do it that is less frantic is to give the players a certain number to beat (maybe 50) and let them add up the results of their attempts to reach it. This is basically like knocking down the hit points of a monster with attacks, but it will feel different if you’re just going around the table, quickly adding tally marks for each player’s roll and, when it gets back to you, rolling a dice timer for each round.

Get yourself a counter device. They’re fun to use and allow you to quickly count up “damage”.

To keep it fast, instead of giving them bonuses for a good ability score or having a skill, just boost the die they roll. So the weenie is rolling a d4 while the stud is rolling a d10. This might simulate the heroes moving rocks out of the way to clear an exit or shoring up a crumbling passageway, and they only have a few rounds to do it.

Make Failure Interesting

Similar to the it-takes-only-one-failure problem we started with, if every challenge is do or die, your heroes are eventually going to die. Instead, look for ways to make failure less lethal but more interesting. A failed challenge might result in…

• Escape of a villain, who will live to fight another day
• Entrapment, from which they can later escape
• Capture, from which they can later escape
• Loss of treasure that could have been won
• Destruction of a magic item in their possession
• Loss of an ally to captivity or death
• A scar, permanent or temporary
• A curse, which can later be lifted by spell or deed
• Humiliation in front of a crowd
• A setback in a hero’s personal quest