When Should I Ask For A Roll?

Gamemaster Doug never doesn’t ask for a roll

My campaign didn’t meet this week, so here’s an idea to tide you over.

Situation #1: your game has a PC (Varion Nightshadow, master thief) who’s breaking into the governor’s mansion.  You ask, what’s his plan to get in.  The player leans back, savors the moment – it’s his chance to narrate something badass. 

PLAYER: “I’m on the next roof, scoping it out.  Are there guards on the walls?”
YOU: “Looks like it’s too cold – they’re all gathered around a brazier in the courtyard.”
PLAYER: “Varion scales the outer wall, then runs along the top looking for the point where the house is closest.  Then he throws a grappling hook to the house roof and swings across over any courtyard guards.”

He’s described his action; so do you call for a climbing roll, then a stealth roll, then a throwing roll next?

(courtesy of dominuself on deviant art - check
out his other Thief pieces)
Situation #2: Varion is now inside the mansion, a priceless piece of art clutched under his arm.  His exit has been cut off, and a number of alerted guards are in between him and the door. 

YOU:  “They’re moving your direction; what do you do? 
PLAYER: “Well, I can’t stay here – I’ll have to give it my best shot to sneak past the guards and out the front door.” 

Do you call for a stealth roll?

A lot of rulebooks would tell you to call for a roll depending on whether it’s a high-stakes situation, or where there’s a reasonable chance of failure.  Now, the “reasonable chance of failure” method assumes a scale with “less-dangerous” on the left and “more dangerous” on the right, with all dice-rolling happening to the right of some threshold.  



I suggest that a better method is to call for a roll depending on the purpose of the scene.



Using this method, calling for a roll in situation #1 would be wrong, and not calling for a roll in situation #2 would be equally wrong. 

In situation #1, the player was moving around, “feeling out” the game environment, and showing you the way his character likes to do things.  The character could fail at these actions, yes, but it wouldn’t be very intersting since you both know that these actions are really just meant to get him into the mansion, where cool stuff can happen.  In situation #2, the player faces a real chance of failure – that is, escaping or being captured could both lead to interesting storylines, and thus, the GM is going to treat failure like it’s a real possibility.

So when you’re about to ask the player “how do you…” ask yourself why you’re asking the question.  Is it because you want to see this character in action, or is it because you’re hoping they’ll fail so you can do this really cool thing you just thought of?  If the latter, call for a roll.