A couple of years ago, then Pixar storyboard artist Emily Coats tweeted pieces of advice on making stories that she had picked up from working with Pixar, which were later compiled on in several places on the internet, such as this io9 post. Later, Dino Ignacio created image macros of the individual rules which I am using in these posts.
Rule #6: “What is your character good at, comfortable with? Throw the polar opposite at them. Challenge them. How do they deal?”
Okay, so you’ve gotta be really careful with this one. This is a great way to challenge a player and provoke character development in their character. It’s also a great way to burn your game to the ground. I have, on more than one occasion, made the mistake of throwing monsters really good at grappling at D&D groups to grim effect. I accidentally killed a party with an animated rug that way. You have to pay attention to the competency gap in your game; that is, on the gap in ability between a character that is an expert at something vs. a character who has no skill with that task whatsoever. In D&D, the competency gap tends to be huge, such that an expert can automatically succeed against a novice, even with circumstantial bonuses in the novice’s favor, every time. In contrast, The Shadow of Yesterday is explicitly designed such that an unskilled character always has a chance of beating a grandmaster. Basically, when you throw a character into a challenge that’s out of their depth, you have to pay attention to your rules set to make sure that you aren’t stacking the deck too heavily against them. If it’s obvious that they have no chance of success, they’re more likely to simply give up rather than attempt to deal with the challenge.
Which takes us back to Part 1: If you’re going to throw a challenge at a character that they are quite likely to fail, you need to be careful about what the consequences of failure are. Putting a character in a situation where they have little chance of success and the consequences of failure will kill or break that character, without the player’s consent, is, quite frankly, a colossal jerk move. You might as well tell the player that a meteor falls from the sky and obliterates their character from the face of the earth. Note the bit about player consent; sometimes players are more than willing to see their characters get broken, whether it’s because they don’t like who their character currently is, or they feel like they’ve fallen into a rut, or because they have a new character they’d like to bring in for a fresh start. The key is that this kind of trap shouldn’t be a surprise to the player. On the other hand, if the consequences of failure aren’t terminal, then it isn’t a bad thing to take a player off guard from time to time.
Once you have the parameters of the challenge, you should consider the avenues left for a character. They might just give up or try the obvious, straightforward approach and fail, both of which are covered above. Or they might ask for help. Depending on the character, just asking for help might represent significant character development. Presenting a loner-type character with a personal problem they can’t solve by themselves is a good way to push them to open up to the group and form closer bonds. This can also be used to push the players into contact with NPC’s who have skills they don’t (and who perhaps are not high in the players’ estimation). On the other hand, a challenge that can be passed to another character that can solve it trivially isn’t much of a challenge. If you don’t want to go so far as to force a character into a situation where they can’t get help, you can at least try to make it important that they take lead instead of deferring to someone else.
A character who can’t ask for help and can’t succeed in an obvious way is pretty much left with improvisation as an approach to solving the problem you’ve put in front of them. Resist the urge to try to figure out how they’re going to get out of the problem ahead of time. It might sound like a good idea to make sure your puzzle has a solution, but you risk preemptively foreclosing on whatever attempt your player tries. If you’ve already decided that they can rob the bank by tunneling into the vault, you might be too dismissive when the player decides to masquerade as a police detective to get access to the vault instead. Basically, you need to keep an open mind about the things the players try and do you best to imagine how it could work. That doesn’t mean you have to award them success at the very first thing they try, but you have to manage the frustration of not knowing how to get past the obstacle in front of them.