I was playing in a sci-fi game and my hacker wanted to set up a dead man’s switch on the environmental systems in a space station: When the melee characters launched their assault, I’d pull the dead man’s switch. The GM had me roll to set up the dead man switch… and then roll every single round to maintain it… and then roll again to throw it even after I’d set it up successfully.
Eventually, given the endless series of checks, I inevitably failed.
Laying aside the fundamental misunderstanding of what a dead man switch is, the negative effect of this sort of thing can be quite severe in an RPG session. In this case, the group quickly realized that we should never, ever try to make a plan: If we just improvised something, it would be resolved in a single roll and we’d have a chance to succeed. If we actually put together a plan, on the other hand, it would just invite lots and lots of dice rolling until the plan failed.
The solution is fairly simple: Let It Ride. Have the character make a single skill check that determines the ultimate success or failure of their endeavor.
Another solution is a complex skill check (making multiple checks until X successes are achieved). These tend to be very elegant in dice pool systems, and when you want multiple checks to be made they’re an effective framework for allowing that without the all-or-nothing of a single check ruining the entire attempt.
GM DON’T #2.1: FAILURE IS POINTLESS
The flip-side of rolling to failure is the “roll pointlessly until you succeed” thing. For example, you’ll often run into games where the PCs need to unlock a door: There’s no time pressure and no consequences for failure, and yet the GM will sit there and have the PCs roll over and over and over again until they finally succeed.
One way to deal with that is something like the Take 20 mechanic: If you can eventually succeed at this, then we can assume that you will eventually succeed at it and we can move on. Letting it ride can also solve this problem by providing the opposite outcome: Your failure on this Open Locks check tells us you are simply not good enough to pick this lock at this time and in this way. (The single check determines your relationship with the lock and until you can substantially change the situation, your character is going to be stymied by that lock).
GM DON’T #2.2: TOO MANY SEARCH CHECKS
A somewhat related problem is when a multi-step action resolution gets broken down into too many discrete parts. This can take many forms, but the most cancerous form I’ve seen in the wild came from GMs who took the Search guidelines for 3rd Edition D&D way too seriously. Those guidelines specified that it took a full action to search a 5-foot square. That’s a useful guideline for combat (when you might want to know how much area you can search during a single round), but some GMs took this to mean that you needed to make a separate Search check for every 5 foot square. So if you searched a 10-foot-wide hallway that was 40 feet long, you’d have to make sixteen (!) separate Search checks.
This isn’t rolling to failure because each chunk is a legitimately separate task. (Failing to search in Square #1 doesn’t mean you won’t find anything in Square #2.) But it murders pace – which is either directly undesirable or undesirable because it discourages players from using the specialties affected by the problem.
The solution here is to collect the tests into meaningful chunks: Searching an entire room (or even suite of rooms) is obvious. Alternatively, if they want to search the dungeon hallways as they move along, let the result of the check ride until they either make a meaningful choice to do something other than search down the hall OR until that check result produces a result (either success or failure) that they can recognize as such (i.e., until that check either finds a trap or secret door or until it fails to do so and the trap happens to them or the ambush pours out of the secret door they missed).
Sometimes you’ll end up with a player who demands multiple checks. In some cases this is because they, too, are following bad mechanical advice (like the “make a check for every 5 feet” misinterpretation of the Search rules). In other cases, it’s a manipulation of metagame information (“I know I rolled poorly, so let’s have that only apply to this one specific area and then I’ll make another check”). Often it’s because they’re irrationally trying to manage risk (“I’ll only search this little chunk so that if I roll poorly the effects will be minimalized” — which doesn’t make sense because your odds of discovering any given hazard remain unaltered, but that doesn’t mean people don’t do it).
Most of the time your response to this is fairly simple: You tell them no.
The exception would be the rare instance where it’s actually effective pacing to stretch out the mechanical resolution. Like a slow motion shot in a film, these are the times when specifically highlighting each small, discreet, tension-filled moment serves to escalate the crisis and leave the table on the edge of their seats.
Identifying these moments is a gut-check, not a science. For example, I was just about to say that it would never be Search checks down a dungeon hall… but then I realized that there actually was a time that I followed a player’s lead in the Tomb of Horrors to separately search every single inch of corridor because that mechanical resolution was so completely right in capturing the paranoia and terror the group was experiencing in that moment.
LET THE GOOD TIMES ROLL
On a closing note, let’s be clear that not every series of sequential rolls with a non-discrete outcome is rolling to failure. We’ve already discussed the situation where each individual check is a separate, meaningful accomplishment. But it’s also true that, for example, combat isn’t a roll to failure even though it involves multiple checks culminating in a single outcome of life-or-death.
It’s also useful to note that rolling to failure can be an effective choice if you’re actually looking at a situation where failure is assured and the interesting question is how long a character can stave off that failure. For example, how long can you say conscious in a vacuum? How long can you hold the door against the werewolves pounding on it from the other side?