DM Advice: Roll at your own risk
Updated: Jun 2, 2020
Tabletop players love to roll dice and see what outcome the RNG gods divine. Sometimes, we love rolling dice so much that we try to roll when it doesn't make sense to. As DM, it's our responsibility to ensure the dice hit the table only when the roll has purpose.
A roll should be made when there is a chance of failure and success.
Roll at your own risk.
The fighter has a Strength score of 16. She stands before a 12 foot wide chasm and needs to reach the other side. "I roll to jump across the gap," she says, hurling a d20 before the DM can respond. Rules as Written (RAW), no roll is required given a ten foot running start. She would clear the gap based on her Strength score alone.
Jumping Your Strength determines how far you can jump.
Long Jump. When you make a long jump, you cover a number of feet up to your Strength score if you move at least 10 feet on foot immediately before the jump. When you make a standing long jump, you can leap only half that distance. Either way, each foot you clear on the jump costs a foot of movement.
PHB. pg 182 | Adventuring
The d20 settles and a Nat 1 taunts the fighter. While rolling 1 has no magical negative effect on Skill checks, house rules often equate Nat 1 to "bad stuff happens." That aside, the fighter has a +2 proficiency bonus, a +4 STR mod, and they're proficient in the Athletics skill. Add that together and the fighter gets a whopping 7 on their attempt to jump across the chasm.
The DM now has a choice to make and must quickly adjudicate:
Treat the DC of leaping the gap as trivial for the fighter and allow her to successfully cross it, effectively ignoring the roll
Impose a failure due to the low results to honor the unnecessary roll and add weight to the RNG result
Find a middle ground: "You manage to clear the gap, but scramble on the opposite ledge, just barely catching yourself and having to pull yourself up."
A DM in complete command of the game may prevent the roll before the player gets attached to the idea of rolling the check. A DM that plays more loose and fast may embrace the roll and invite the Nat 1 chaos, sending the fighter plummeting 40ft, and turning a trivial task into a memorable, if not deadly, moment.
Ultimately, rolling in a scenario where the default is success invites the possibility of failure. Ergo, roll at your own risk.
Similarly, the party Wizard is looking for clues in town at the local tavern. He's met a friendly barkeep and they chat amicably. This barkeep is notorious for collecting rumors and is a huge chatter box. The Wizard says, "I want to roll to see what they know about the stolen crown."
But what is the Wizard actually rolling for? The DM glances at their notes:
Either the friendly barkeep knows or he doesn't. Rolling to see what he knows is moot, unless the situation calls for it. If the Wizard rolls to "see what the barkeep knows" it invites an unnecessary chance of failure and potentially closes off an otherwise viable source of information just because RNG.
A more appropriate scenario to encourage rolling (because we love to roll dice!) would be an unwilling informant that needs to be convinced to divulge their information. An Intimidation check or a Persuasion may do the trick if the barkeep knows something and is withholding it from the party.
If the bard fails their Persuasion check it's because the barkeep is actually unwilling to share the information and the attempt at persuading wasn't "persuasive" enough to convince them.
In summary, undue heartache and RNG fiascos can be avoided by knowing when to call for a roll and when the DM, or a player, are rolling at their own risk. A roll should be made when there is a chance of failure and success. If the default and concrete outcome is success or failure then a roll shouldn't be made. Rolling implies there is a chance that the resulting number can change the outcome. For example, a low-level party is trying to convince the Big Bad Evil Guy (BBEG) to reveal their ultimate plans, something this BBEG would never do. Asking for or allowing a roll signals to the players that there is a chance they'll succeed. If they roll a Nat 20 + 5 it suddenly puts the DM in a position where they now have to consider: can the BBEG be convinced here? Sometimes it's okay to forego the roll and tell the players "you try to convince Mr. Evil Guy but he is too keen and will not divulge his master plans."
Roll at your own risk, and have fun with the outcome.