“I would like to sneak down the hallway.” the rogue states.
“Alright, make a stealth check.” says the GM.
The rogue stares forelornly down at her newly rolled 11. There ends up being nothing down the hallway anyway. “I uh… head back to the group to tell them?” she asks, meta-hoping to rid herself of that roll before heading out again.
We GMs have always been an situations where we call for rolls that give the player some meta-knowledge. An openly rolle dstealth check, perception check, or insight check Whether you intend to or not, the meta-knowledge of the number that the PC rolled is going to influence their actions. Sometimes overtly, sometimes subtly. At the very least, if the PC rolls very high or very low, it removes much of the tension of mystery as to if they are likely to be discovered by anything looking. While one possible answer to this is to roll those dice for the player in secret and not tell them the result, I find this removes some agency for the players.
We have also all been in the situation where you call for a stealth check when a PC starts sneaking or hiding. Often in large dungeons, there will be many a stealth check rolled as the rogue sneaks around, but very few are will be contested. Why? I mean, yes, rolling dice is fun but you don’t pre-roll attack rolls at the start of your turn just in case you attack. Do you?
This also applies to other situational ability checks as well. How often have you asked for a strength check when a character tries to open a door, only to have it fail and everyone else asks to roll strength checks as well… and then ask to roll some multi-character aided strength checks… and then ask if they can try again because they have time. Did any of those checks really matter? Were there any consequences to failing? I find this happens quite a lot when dealing with mission-critical rolls. If the characters HAVE to get into the crypt to get the axe of power, or you really want them to get a piece of information out of an interrogation subject, you end up giving them a second try, then a third, aaaaaand a fourth.
The time to pick up and roll a die is when it really matters – when there are consequences to failure.
When the rogue asks to sneak down the hallway or hide in the plant pot, say ‘ok’. They are sneaking or hiding, cool. They have no meta-knowledge about how well they’re sneaking/hiding, and they’re not making unnecessary rolls. The time to ask for the associated roll is when the rogue is three corridors into the dungeon and sneaking past the open door with a beholder insider, or at the point when the guard walks by the plant pot. When there is something to oppose that check and the consequences for failure are real.
For other skill checks, there are situations that involve consequences and require rolls. If there is a timeframe to complete a task, then the number of tries is limited and rolls are called for. This is especially true for skill challenges mid-combat. You can also create consequences. An exploding trap on a lock is a sure consequence of failure to disarm or pick the lock. A heavy door may jam shut or fall on the character if wrenched wrong.
You may even want to entertain a slightly different view on what skill checks are. What if skill checks do not determine a character’s performance, but actually set the reality of the situation? While a successful investigation check may let the players find some useful information, a failed check doesn’t mean the character failed to find the information, it means that it was never there. A failed strength check to open a door means it is barred from the other side and requires a different approach. A failed charisma check means the king had already made his mind up to disapprove of the PCs’ plan and is now just telling them. The state of the world can be formed by the dice and, in that case, re-roll has no meaning.
So next time a player asks you if their character can do something, ask yourself if there are any consequences to failure. If not, don’t ask for a roll, or at least wait until that roll becomes necessary. Simply narrate the outcome in exquisite detail and move on.