When do we roll the dice?
As I said last week, the best reasons to roll dice are to build tension, add unexpected turns, and decide with supposed impartiality whether a character succeeds or fails in their action.Let's focus on that first reason: tension. That argues that you should minimize the number of rolls. Much like cheap scares in a horror movie a little goes a long way. Too much ruins the effect. I think one should generally avoid rolling dice as much as possible and let the plot or the story our telling guide the way. Save the dice for dramatic moments when the can heighten excitement. Don't roll when there is nothing to gain.
That means that if the success or failure of an action won't cause a real and meaningful change to game, either to enhance the tension and mood or to add useful and interesting twists, then you just let the player characters (PCs) be successful and move on to the important part of the story.
For example if the heroes are breaking into a castle and they need to climb a wall, ask yourself whether a failure adds something to the story. If they fail to climb this wall will the story grind to a halt? Then let them get past it. Otherwise you are shooting yourself in the foot, ruining the game for some vague sense of "following the rules" or "enforcing realism".
Is the question whether they succeed before someone notices? Then you should break out the dice and do a quick roll with the stakes clearly laid out. If the die roll can lead to interesting complications then by all means roll but make sure success and failure are interesting. So in this example success takes the group to the next stage of the story while failure leads to their sneak mission becoming a battle, perhaps with a timetable as the defenders muster a defense of the castle.
Returning to the idea of realism, perhaps you are wondering if someone will fall in the process of scaling the wall. In that case I refer you back to the first two questions. If you want them to get past the wall, then falling runs counter to that. What if someone blows their rolls a couple of times and then gives up? The result is that have you irritated a player, wounded their character, and wrecked your own plot. If on the other hand if you see interesting probabilities where they might be discovered, falling might be a reasonable thing to check. Though again you've just hurt a character who now likely has arrows shooting down at them. Hopefully your concept includes some interesting effects from the fall, such hitting a crocodile filled moat.
Failing should improve the story, not derail it. The same goes for any roll. Everything should work to drive the plot and story forward.
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