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How To Handle Skill Checks in D&D

The most important question to ask yourself before asking for a skill check is, "what happens on a fail?" If you can't think of anything, or if the answer is "nothing" then there's no reason for you to call for a skill check. Just describe them doing the task and continue on. If the answer is "it just doesn't work this time, try again" then that's something you should think more on. Don't worry, they're looking up their skill modifier and asking what a skill modifier is for the 100th time (let someone else answer), then they have to decide which dice isn't in "dice jail" before rolling and forgetting how to add numbers, so you've got some time to think.

When things go wrong

The ideal fail state for skill checks is "you have to try something else" and not "try again." This forces players to brainstorm new solutions and improv as things go wrong, which is ultimately what they're there to do. Rerolling a lockpick check is boring, having the lock jam audibly is more interesting, as now they have to find a new way to get the door open and deal with the patrol that's investigating the noise.

For physical skill checks (running, climbing, balancing) you can have some sort of physical injury occur. This depletes their health and resources, which is a built-in way of punishing failure and making retries unappealing. You can treat it as roughly equal to getting hit by an enemy in a normal difficulty encounter and adjust it upwards / downwards depending on how high the stakes are (or how close they're getting to the boss). You can quickly check the appropriate damage for a given CR on the Monster Stat Block page. Some checks have a built-in outcome, like failing to detect or disarm a trap will always trigger it.

When it comes to non-physical skill checks (knowledge, social, etc.) without good failure conditions then you risk "dogpiling" where everyone in the party gives it a try. If you allow this then the players will almost never actually fail a skill check due to the extremely favorable odds. If there's no chance of failure, then we're back to there being no reason for you to call for a skill check. If it's something you really want them to know, then you can have the opposite problem where they all actually fail the check. In such situations it might be helpful to think of "passive" scores, similar to perception. Ask for their passive arcana score by adding 10 to their modifier, then whoever says the highest number tell them the critical information.

To stop dogpiling you can require that players actually have a good reason to attempt the check, like a history check might require them to be trained and versed in this part of the world, or have a relevant background that makes them familiar. Don't let two players use the same reason as each other either, it's an improv game so they can come up with their own. You can also make the punishment for failure dissuade the others from trying, or outright restrict their ability to do so based on new complications that the first failure caused.

Seems trustworthy

If your players are habitual insight checkers, have the first player that makes the insight check convince the others of their result. If your friend and adventuring companion says someone is trustworthy, then you're more likely to believe them. A failed insight check could have their character following the drow to "a more secluded location" before anyone can protest. Maybe if they're doing an insight check on yet another barkeep after asking for rumors, you could tell the person that rolled to give a rousing speech to the others about why this guy is trustworthy. If you call for a check and it fails, you should try to complicate the situation in such a way that the players have to try another approach and not just the same one again.

A good rule of thumb when it comes to skill checks is this: a successful skill check allows the players to dictate what happens next, while a failed one allows the enemies to dictate what happens next. This push-and-pull between the protagonists and antagonists is what makes stories interesting, and it will make your sessions more fun as well. The Skill Definitions list can help you figure out which skill check is appropriate for a given situation.

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