I have to say, I mess this up all the freaking time when I GM. If something doesn’t matter, why are we spending our time at the table rolling for it? I think I could speed up play by improving here, but I want Lost Worlds to try and be pretty clear about when you should roll, and when you shouldn’t.
If success is guaranteed, don’t roll. Are you shooting an arrow at the broad side of a barn from 50 paces? You hit, and we’ll move on.
If failure doesn’t matter, don’t roll. Note that this is different than asking whether success matters. For example, if your party scout is in the woods and wants to climb a tree for a better vantage point, you could ask for a climb check, but if it’s failed, the character is just going to try again. Sure, success grants a better vantage point, so success matters – but failure doesn’t matter a bit.
If there is no time constraint and quality doesn’t matter, don’t roll. I could see rolling in some cases where there isn’t any time constraint. For example, if quality matters, like a character is trying accomplish a rare feat or pen a masterpiece novel or something, go ahead and roll to see if it’s truly exceptional quality. Otherwise, if the players have all year, why roll? All you’re doing is making them keep rolling again and again until they get it, and I’m not sure why that’s what we want to be doing at the table. Even if quality isn’t important, if the character has to accomplish the task now, then by all means roll for it!
Rolling the die should be about drama. The result should matter. What other times does rolling the die feel like a chore instead of adding drama to the game?