Why I Hate Skills

Boy I would struggle with improvising that in the moment, if the players ask me about something unexpected.

Good thing players never do anything unexpected, I guess. :-/
The instance that made me think the procedure up wasn't actually a knowledge check, but rather someone following a party member. There's no real benefit to them not knowing they are being followed, and the "roll with no obvious cause" isn't something I'm a fan of. So I call for a roll at a DC set by the stealthiness of the follower and on a fail the character 'has a feeling' that they are being followed, but no specifics. On a close fail maybe they catch a glimpse, On a pass they get some concrete description. In this case part of the rationale is that professional adventurers have a base level of situational awareness and don't like being snuck up on.

The point is that in any event the player gets a piece of information that they can act on and things keep moving forward.

On the knowledge check side it's very much driven to begin with by the character in question. If they have a background that applies (this is Shadowdark, so no skills) then I'm happy for them to get at least a sense of what those runes mean, or a vague memory about thing Y (or whatever). A character with no applicable background will just get a pass/fail check and probably with a high DC. For the character with a background that applies I'll set the DC based on how obscure the information is and the results on on close they came to success, or on a success they just get the information.

Part of the point here is that with a little bit of information the party has some direction if they want to learn more. They can go to a library to research, or find an expert, or whatever. In both instances I'm essentially adding some fail forward momentum to the binary pass/fail system.
 

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The instance that made me think the procedure up wasn't actually a knowledge check, but rather someone following a party member. There's no real benefit to them not knowing they are being followed, and the "roll with no obvious cause" isn't something I'm a fan of. So I call for a roll at a DC set by the stealthiness of the follower and on a fail the character 'has a feeling' that they are being followed, but no specifics. On a close fail maybe they catch a glimpse, On a pass they get some concrete description. In this case part of the rationale is that professional adventurers have a base level of situational awareness and don't like being snuck up on.

The point is that in any event the player gets a piece of information that they can act on and things keep moving forward.

On the knowledge check side it's very much driven to begin with by the character in question. If they have a background that applies (this is Shadowdark, so no skills) then I'm happy for them to get at least a sense of what those runes mean, or a vague memory about thing Y (or whatever). A character with no applicable background will just get a pass/fail check and probably with a high DC. For the character with a background that applies I'll set the DC based on how obscure the information is and the results on on close they came to success, or on a success they just get the information.

Part of the point here is that with a little bit of information the party has some direction if they want to learn more. They can go to a library to research, or find an expert, or whatever. In both instances I'm essentially adding some fail forward momentum to the binary pass/fail system.
Sprinkle in some take 10/20 sensibilities, and this pretty much sums up my preferred approach too.
 

One "fail-forward" or "yes, but" thing approach comes to mind: if a character fails a check, instead of not seeing something, or not knowing something, they spend some resource like "inspiration" or "willpower" and it still works.

I could see an implementation where this is limited to certain difficulty levels and training levels - say, if you're proficient (5E style) or trained (4E) style, anything that is below DC 15 or below your passive check (10+skill modifier) you know, you're just rolling to see what this knowledge costs you. (5E Expertise or 4E Skill Focus increases the range this is possible).
If you had a system where you want to improve skills only if you use them, you could say any time you spent a resource to overcome a 'failed' check, you can also gain experience toward that skill.

Of course, this doesn't work if you don't have such a resource system and don't want to introduce it, either.
 

The instance that made me think the procedure up wasn't actually a knowledge check, but rather someone following a party member. There's no real benefit to them not knowing they are being followed, and the "roll with no obvious cause" isn't something I'm a fan of. So I call for a roll at a DC set by the stealthiness of the follower and on a fail the character 'has a feeling' that they are being followed, but no specifics. On a close fail maybe they catch a glimpse, On a pass they get some concrete description. In this case part of the rationale is that professional adventurers have a base level of situational awareness and don't like being snuck up on.

The point is that in any event the player gets a piece of information that they can act on and things keep moving forward.

On the knowledge check side it's very much driven to begin with by the character in question. If they have a background that applies (this is Shadowdark, so no skills) then I'm happy for them to get at least a sense of what those runes mean, or a vague memory about thing Y (or whatever). A character with no applicable background will just get a pass/fail check and probably with a high DC. For the character with a background that applies I'll set the DC based on how obscure the information is and the results on on close they came to success, or on a success they just get the information.

Part of the point here is that with a little bit of information the party has some direction if they want to learn more. They can go to a library to research, or find an expert, or whatever. In both instances I'm essentially adding some fail forward momentum to the binary pass/fail system.

(I know you know the following, so the "you" is generic...)

With the benefit of hindsight, one way of handling this would have been to quickly describe some NPCs who could be following them. When the player says, "Do I think any of them are following me?" you can say, "I don't know, do you?"

Then, if they want to start taking some detours and see if any of the NPCs continue to be behind them, they might refine their guess. And maybe there are some opportunities for skill rolls (hiding, climbing drainpipes, etc.) along the way.

Of course, even if there is, it could all still be coincidence.

I think this illustrates two approaches to gaming, both perfectly valid:
  • In one version, the player doesn't know how one susses out a tail, and wants to lean into the fiction of "my skilled character would know how to spot a tail based on their movements, because in the movies that's what trained such-and-suches know how to do." (With a dose of "We don't want to take up half our game time playing out whether or not there's a tail, and the DM doesn't feel like making up a bunch of NPCs.")
  • In the other version, the player wants to figure out a solution to the situation themselves, which can be done even without any actual expertise (such as lockpicking).
 

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