When You Should Be Rolling Dice
Time and time again, your players will ask to make rolls for their ability checks. The rogue will ask about a Stealth check, or the Bard will ask about a Persuasion check and sometimes a player will just roll their dice a few times and then inform you they got a natural 20. Like that means anything when there is no context for a roll.
When players are given the chance to roll dice, there should be a chance of meaningful failure, and when a player takes it upon themselves to decide when to roll dice, they have no idea if there is a chance for failure, let alone a chance for meaningful failure. Some people just like the sound their dice make when they roll them.
Rolling with Style
There are plenty of times when going through a dungeon a sneaky character will want to be stealthing, and so you have them roll a Stealth check, but the problem is, there was no danger. If a player rolls their dice and they get a low roll, they are going to be constantly trying to figure out when they can reroll that check; and that is the direct opposite if they get a high roll asking if they can just carry over that roll. When they roll a check beforehand, they are focusing more on the mechanics of the game than the world their character is in.
What should be happening at your table is a sneaky character informs you that they are trying to be stealthy as they move through the spooky caverns, you make a mental note about it, and when the time is right - you ask for that Stealth check.
Now, in this hypothetical, when is the right time to ask for that Stealth check? When there is a chance for meaningful failure. This might mean when a rogue stumbles into a room of sleeping goblins, when a patrol is walking down the corridors, when a trap relies on loud noise or lots of movement or any scenario you can think of when its important for the rogue to be sneaky.
This prevents players from trying to reroll their checks to get a better number, creates suspense, and makes it easier for the GM when comparing competing ability checks.
Wait for iiiiiiiiiiiiit
When playing a game, part of the fun the GM creates is suspense. If players at your table aren’t rolling their ability checks with bated breath, there is no suspense. That suspense creates tensions and pulls on the nerves, when the dice comes up well for the player they are hit with a rush of endorphins and that pulls them into the game and increases their enjoyment.
When they come up with a fail on the dice, their thoughts aren’t racing to how or when they can reroll this for a better result. Their thoughts are dreading what the consequences are for their character, not about mechanics. This helps your players focus on the world everyone is building at the table.
What it means to fail meaningfully
When there is a chance for meaningful failure this means that if a roll were to fail, there are consequences that will affect the character in a big way. If they are trying to use a Persuasion check on someone who is already their friend to do something that the friend will already do, there is no point in rolling that check. On the flip side, if they are trying to make a Persuasion check on someone who is their mortal enemy and will never listen to them, that’s also a wasted roll.
In both cases, no matter what they roll, their roll will have no effect on the circumstances. Same goes for any other ability check. If they are asking to roll dice for something that they will succeed at no matter what, then they are just playing with weird plastic polyhedrals and not the game. By keeping those rolls to specific, meaningful moments it will keep them focused on the game, not their die.
When players are forced to only roll when meaningful failure is coming up, it helps them know when their actions have consequences. No longer is a roll separated by 10 or 20 minute gap from the consequence, now their rolls are impacting the game immediately. That is an intense feedback that will help players be more engaged at the table as each die roll means a consequence now, not later or maybe never.