D&D 5E How can you add more depth and complexity to skill checks?

Ovinomancer

No flips for you!
I'm not a fan of having multiple rolls to determine the outcome of one skill/ability challenge. I don't feel a challenge should be a best out of three affair. If the first roll succeeds, you succeed the check. It shouldn't be nullified by then failing a second roll. If more than one roll is required, the fiction should justify the second roll. For example:

If a player fails a jump challenge, it is within reason that a second roll could be made by the falling player, or a nearby ally, to try and grab on. But there should also be consequences if the check fails. Choosing to try and grab the hand of your friend, could result in being pulled down yourself if you fail the check.

In general though, I feel less rolling is better. The complexity should come through consequences to the outcome of the roll, not from the number of extra rolls. Extra rolls just arbitrarily make a challenge harder (and make the outcome more random), which raises the question why you wouldn't raise the DC instead and do away with the extra rolls.
That's not what's going on with the 3 check method, though. One failure doesn't negate, it adds a consequence. So, for a complex challenge, you make three rolls. If you succeed on all three, you complete the challenge with no consequence. If you fail on one, you complete the challenge, but suffer a consequence related to the roll failed. If you fail 2, you fail the challenge and suffer a consequence. My variation on this is doing something that's complex, but that you'll probably succeed at if at a cost. So, outside of three failures, you will complete the task, but you'll take a complication/consequence/cost for each failure, related to the failure.

In case it wasn't obvious before, what ON EARTH has this to do with the topic of the thread?!
I often find that how you deal with checks directly informs what you might think is missing/flawed with the skill system. It's a definite matter of approach as to where the skill system might let you down. As the OP still hasn't provided a clear goal or problem statement, just an ask for more skill stuff, a discussion on how skills can be used in the base system -- approaches and outcomes -- is a useful input to discussing the differences in how the skill system should be adjusted. I, for one, don't have any issues with the current skill system, but that's because of how I approach it. My first 5e campaign, when I was much more in line with @Crimson Longinus' approach, I had lots of additions to the skill system to do things. I changed my approach to how I play and those issues fell off. Now, I have a different set of issues that are more structural on how you use ability checks rather than mechanical on what you do mechanically when you use ability checks.
 

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Ovinomancer

No flips for you!
@Ovinomancer: I’d be very interested to hear your thoughts on fiction-first skill challenges. My experience trying to port Skill Challenges to 5e has been that it felt at odds with 5e’s resolution style. Like, I could sort of make it work, but I get better results using a more player-reactive system like the Angry DM’s Tension Pool for complex tasks. Then again, I was one of those DMs who never quite “got” Skill Challenges during my time DMing 4e, so maybe my attempts to port them over have struggled from the same core disconnect with the Skill Challenge system in general.
I never got them in 4e, either. It wasn't until the middle of my run in 5e that I finally tripped to how some people just lurve, lurve, lurve skill challenges and others, like me at the time, either bounced hard or went meh.

I tend to not read Angry, but I'll look at his tension pool stuff to see what he's saying there and how it might relate. I've sometimes been pointed to Angry's stuff saying the same things I said, so there's at least some commonality in view there. I just tend to find him too long winded. And, yes, I'm keenly aware of the irony. ;)

EDIT: So, I found the post and skimmed it, and there's some similarities in that it's a tool for adding complications, but it's largely a different thing. Angry's Tension Pool is a pacing tool, primarily. The fiction first skill challenge is a resolution tool, primarily. There's some similarities in the middle, but they're passing in that, as Angry said, it's the job of the GM to complicate PC's lives.
 

Charlaquin

Goblin Queen (She/Her/Hers)
I never got them in 4e, either. It wasn't until the middle of my run in 5e that I finally tripped to how some people just lurve, lurve, lurve skill challenges and others, like me at the time, either bounced hard or went meh.
My feeling on them during 4e was that “the best thing you can say about them is that they don’t suck if your players don’t know they’re happening.” It wasn’t until the 5e playtest that I came across a guide to running them (that I think was written by @iserith?) But by then I was like “eh, I won’t need them in 5e.”

I tend to not read Angry, but I'll look at his tension pool stuff to see what he's saying there and how it might relate. I've sometimes been pointed to Angry's stuff saying the same things I said, so there's at least some commonality in view there. I just tend to find him too long winded. And, yes, I'm keenly aware of the irony. ;)
I don’t blame you. He takes like six articles to explain a system that amounts to:

Add a d6 to a visible pool of dice whenever a player takes a time-consuming action. Roll all the dice currently in the pool whenever a player takes a risky action (do both if the action is both risky and time-consuming). If you would add a die to the pool when there are already six dice in it, instead roll them all and then empty the pool. Any time you roll the pool, a complication occurs if any dice come up on a 1. This works for basically any situation with mounting tension, by giving a players a visual representation of that tension building up, and making the risk of complications build, climax, and then fall. It can also be used to track time, with each die representing roughly 10 minutes in the dungeon, or roughly 4 hours overland. In this case, you also add a die whenever the appropriate amount of time passes in game.
 

I'm not a fan of having multiple rolls to determine the outcome of one skill/ability challenge. I don't feel a challenge should be a best out of three affair. If the first roll succeeds, you succeed the check. It shouldn't be nullified by then failing a second roll.
Just roll them all at the same time.
 

I think you might want to take a page from your own book and calm down. I've talked about issues that can arise from allowing players to ask for skill checks, and they most definitely can arise. You might avoid them, and kudos to you, but they exist. No approach is foolproof (my own has problems, just not the ones you imagine it does).

Asking for skill checks does the following:

1) It puts the GM into the position of having to guess what the PC is actually doing.

--The usual answer to this is that sometimes it's obvious. Granted, sometimes it is, but when you say this you're also saying that sometimes it's not obvious and the GM guesses.

--The answer to that is that the GM can always ask for clarification. This means that you're perfect and never are in a situation where you think it's obvious, but what you think isn't what the player thinks. I find that hard to track because RPGs have an inherent information asymmetry between the GM, who knows lots, and the player, who only knows what the GM tells them. This means, to avoid this, you're always aware of not just what you're thinking/know but what the player is thinking/knows. I know my players really well, and I'm good at reading rooms and people, and I can't do this. If you can, awesome, but that's you, not the playstyle. It also means that you end up where I start, so not seeing a lot of savings here, in this case. Even if you avoid the information asymmetry, you're still doing what I do when your first pass doesn't work, so this isn't a terribly great response.

2) It makes the game one where a lot of the time players are asking the GM questions rather than doing things.

-- this is a preference issue, but I can definitely say that the weird animal tangent from earlier posts exemplifies this. It's the kind of additional information asymmetry that's often paired with having players ask the GM if their character knows things. You stated above that the check was a tool to get your to create more lore for your games based on players asking, but, from other threads, this is kinda circular because you also are very much against "metagaming" or using player knowledge so players have to ask you for checks to see if their characters know something. Here the playstyle approaches reinforce, and show that if you're going to make players check with you on character knowledge anyway you're also probably going to be very strongly in favor of asking for checks because it streamlines this process. I don't do the former, so the latter streamlining is useless to me as a tool.

That's describing what asking for checks does.

Again, the pea being moved here is that "some situations" is trying to cover a lot of ground and it tacitly acknowledges that "some situations" means "other situations" exist. Skipping the step where the GM determines what "situation" this is, and possibly making a mistake of situation, by just having players say what their characters do (which is the fallback safety point of asking for checks in non-obvious situations) is, to me, not a problem. It's fast, it's easy, I don't lose time, there's not formula my player have to follow -- they just tell me what they want their characters to do. I mean, I'm very confused that asking players to engage the fiction by describing what their characters do, in an RPG no less, gets labeled as "dogmatic" by someone arguing that they should be able to just press buttons on their character sheets and let the GM fill in the blanks. Scratch that, not confused, flabbergasted. It's a very weird place to be, being told that expecting players to actually say what their characters do is dogmatic. Very weird.
Based on this thread I have no difficulty believing that reading implicit communication or being able to decide which situations call for lengthy and detailed description and which for brevity so that the story can move on are not your fortes. So by all means keep doing what you're doing, I don't care.

+ + +

Now relating to actual topic, I'd like to mention one very basic thing that I think many GMs still overlook. The players choose the skills for their characters for a reason (this naturally applies to any choosable trait or feature.) So when designing and adventure, actually look at the character sheets of the party. Note what skills and other traits they have chosen, and try to come up with ways those things actually could be relevant for the adventure. Such things of course need to feel organic, you can't just place a random singing contest on the middle of the dungeon so that a character can use their performance skill (or can you?) And often this can actually give you ideas for the adventure and it becomes more nuanced and interesting for it. And whilst you cannot shove every skill in every session, you should try to avoid a situation where the player starts to wonder why the hell they picked 'animal handling' when there is never any situations where the characters could meaningfully interact with animals.
 

Ovinomancer

No flips for you!
Based on this thread I have no difficulty believing that reading implicit communication or being able to decide which situations call for lengthy and detailed description and which for brevity so that the story can move on are not your fortes. So by all means keep doing what you're doing, I don't care.
I said they were things I do well. I work in a customer environment that requires skill at reading people, so, yeah, you just showed that you don't read what I say or that you're willing to ignore it for the jab.

Now relating to actual topic, I'd like to mention one very basic thing that I think many GMs still overlook. The players choose the skills for their characters for a reason (this naturally applies to any choosable trait or feature.) So when designing and adventure, actually look at the character sheets of the party. Note what skills and other traits they have chosen, and try to come up with ways those things actually could be relevant for the adventure. Such things of course need to feel organic, you can't just place a random singing contest on the middle of the dungeon so that a character can use their performance skill (or can you?) And often this can actually give you ideas for the adventure and it becomes more nuanced and interesting for it. And whilst you cannot shove every skill in every session, you should try to avoid a situation where the player starts to wonder why the hell they picked 'animal handling' when there is never any situations where the characters could meaningfully interact with animals.
This actually goes directly to the difference I've been trying to illuminate. Intentionally placing challenges by looking at character skill selections is definitely one way to do it, and dovetails nicely into letting the players feel their skills matter, but only really has lots of value in games where asking for rolls is the approach most often used. This is because you put out a challenge that expects the ask, and so everyone's rewarded. It also leans into presenting a challenge with an expected solution.

The other way is to not do this at all. I honestly couldn't tell you what skills the PCs in my game actually have outside of a few -- I know the ranger has perception and nature and the wizard arcana, but I couldn't tell you much more than that. I'm crafting a problem in my prep, one that doesn't have a solution planned by me, like the performance/singing challenge above. Instead, I put obstacles down between where the PCs are and where they want to be and let them tell me how they're going to engage that problem. It might be that I present a situation where the PCs want to gain an audience with the king, but they don't have the social clout to do it, what are they going to do? A PC might decide that gaining a noble patron is a good way to go, and so decides to sing to gain that patron's attention. My initial framing has nothing to do with singing, and doesn't expect it, but the players have the freedom to approach the problem however they want and use the skills and abilities of their character. This part of the approach is to frame problems, not solutions. My player get good use of their skill choices not because I design challenges with those skills in mind, but because I don't and allow the freedom to approach the challenge to my players.

Both are valid approaches, and engage the player choices, but how you do skills and how you structure challenges lead to very different play experiences. One of these (or some other way) is the best way to play, and it's the one that's fun at your table. They do result in very different play experiences, though, even though there are superficial differences.
 

I said they were things I do well. I work in a customer environment that requires skill at reading people, so, yeah, you just showed that you don't read what I say or that you're willing to ignore it for the jab.
I read that you said that. Then I also read your diatribe about you struggling with those things.

This actually goes directly to the difference I've been trying to illuminate. Intentionally placing challenges by looking at character skill selections is definitely one way to do it, and dovetails nicely into letting the players feel their skills matter, but only really has lots of value in games where asking for rolls is the approach most often used. This is because you put out a challenge that expects the ask, and so everyone's rewarded. It also leans into presenting a challenge with an expected solution.

The other way is to not do this at all. I honestly couldn't tell you what skills the PCs in my game actually have outside of a few -- I know the ranger has perception and nature and the wizard arcana, but I couldn't tell you much more than that. I'm crafting a problem in my prep, one that doesn't have a solution planned by me, like the performance/singing challenge above. Instead, I put obstacles down between where the PCs are and where they want to be and let them tell me how they're going to engage that problem. It might be that I present a situation where the PCs want to gain an audience with the king, but they don't have the social clout to do it, what are they going to do? A PC might decide that gaining a noble patron is a good way to go, and so decides to sing to gain that patron's attention. My initial framing has nothing to do with singing, and doesn't expect it, but the players have the freedom to approach the problem however they want and use the skills and abilities of their character. This part of the approach is to frame problems, not solutions. My player get good use of their skill choices not because I design challenges with those skills in mind, but because I don't and allow the freedom to approach the challenge to my players.

Both are valid approaches, and engage the player choices, but how you do skills and how you structure challenges lead to very different play experiences. One of these (or some other way) is the best way to play, and it's the one that's fun at your table. They do result in very different play experiences, though, even though there are superficial differences.

That the GM has 'a solution' in mind doesn't meant that has to be 'the solution,' nor preplanning some potential situations where certain capabilities are more likely to matter in any way prevent such situations also arising emergently. That's the thing, you can do both, you should do both!
 

Charlaquin

Goblin Queen (She/Her/Hers)
That the GM has 'a solution' in mind doesn't meant that has to be 'the solution,' nor preplanning some potential situations where certain capabilities are more likely to matter in any way prevent such situations also arising emergently. That's the thing, you can do both, you should do both!
When you plan “a combat encounter,” even if you believe that you are open to the possibility of non-combat resolutions, you put your players in the position of having to convince you to let them bypass what you planned. It sets up combat as the default solution, which will always be a valid option, whereas alternative solutions have to be justified. Likewise, when you plan to call for “an athletics check,” you put the player in the position of having to justify use of a different skill.

Granted, if you plan to use skills your players’ characters a proficient with, they may not feel the need to justify using another skill. They’re probably going to be happy for the obvious opportunity to put that skill to use, just like a player with a combat-optimized character will be happy for the opportunity for a fight. However, if you present obstacles with no planned solution, the optimal strategy becomes choosing the approach that you think is best suited to your goal, rather than choosing the approach you think the DM set you up for an opportunity to use.
 

Ovinomancer

No flips for you!
I read that you said that. Then I also read your diatribe about you struggling with those things.
What I said was that I was good at reading people, that I knew my audience really well, and that I would still make mistakes of intention, largely due to information asymmetry. You responded saying that I struggle with things. I mean, I guess if you need to double down to keep the insults alive, you do you.


That the GM has 'a solution' in mind doesn't meant that has to be 'the solution,' nor preplanning some potential situations where certain capabilities are more likely to matter in any way prevent such situations also arising emergently. That's the thing, you can do both, you should do both!
Human nature means that having a solution in mind will mean the GM tilts the situation towards that solution. This fundamentally shows in how the GM describes the nature of the challenge -- the part of the game where the GM describes the environment will be configured towards the expected result. You see this all the time in the published adventures, where they list a skill and DC to get information or bypass the challenge. Traps are usually a huge culprit for this, because the mechanism the GM describes is curtailed to a narrow set of solutions.

All of your responses here are platitudes. "Do both," with no examples or principles for approach how you would do both. "Sometimes it's obvious," which elides those times when it isn't and it's not recognized. It's just general responses that don't actually detail an approach or how you should choose which to use at which points. And, they are fundamentally different approaches -- you can't just "do both." The principles of how you adjudicate actions differ, the focus of gameplay differs, and the feel of the play is different.

What it appears like to me is that you're saying that my approach is just making stuff up when needed or putting spotlight on a PC, and you do that, so you "do both." But, that's not what I'm doing, what I do is structurally different from letting a roll prompt the GM to make up more lore or from going off prep. That's just good GMing with your approach, it's not simulating my approach.
 

When you plan “a combat encounter,” even if you believe that you are open to the possibility of non-combat resolutions, you put your players in the position of having to convince you to let them bypass what you planned. It sets up combat as the default solution, which will always be a valid option, whereas alternative solutions have to be justified. Likewise, when you plan to call for “an athletics check,” you put the player in the position of having to justify use of a different skill.

Granted, if you plan to use skills your players’ characters a proficient with, they may not feel the need to justify using another skill. They’re probably going to be happy for the obvious opportunity to put that skill to use, just like a player with a combat-optimized character will be happy for the opportunity for a fight. However, if you present obstacles with no planned solution, the optimal strategy becomes choosing the approach that you think is best suited to your goal, rather than choosing the approach you think the DM set you up for an opportunity to use.
I don't see it that way, though the thinking you describe is how some GMs approach it, especially with combat encounters. But I merely see it having prepared certain mechanically somewhat more involved things in advance. Like if there is a situation where combat might ensue, then it probably is the best to have the stats of those creatures at hand instead of scrambling to find (or write!) them when it turns out that the characters decide to solve the issue with swords. Being prepared allows the situation proceed smoothly, the suspenseful and tense escalation of hostility directly leading to the combat without being interrupted by the GM having to sort out the mechanical details. Same with many of the more complex skill usage mechanics being discussed in this thread, having the the framework ready will help. And sure, you cannot be prepared for everything and more importantly you shouldn't be fixated on what you planned having to happen. My favourite moments are when the players resolve a problem in some utterly surprising and unexpected manner. So yeah, again, you can do both, be prepared and be flexible; these things don't need to be enemies.
 

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