Improving Your Skill Checks

“Just because a player is asking to do something that is related to a skill check, it does not mean you have to ask for one!” – Me, in this post, right now.

One of the greatest tools in the DM repertoire is asking for skill checks to determine how the story goes. This is more of an art than a system to follow since every DM is different, and every level of risk varies between individual players and steps they want to take. Some DMs ask for a check for everything relevant to a skill while others lean more into following a narrative without the interruption of a dice roll. So where should we land?

A major refrain you will have to take my posts with is that this is not something I think all DMs need to follow, but just some aspects to consider if you feel one of these will help improve your game. Every table is different so do what is most fun for the whole table! 

When To Ask for a Skill Check

I referred to this earlier, but knowing when it feels best at your table to ask a player to make a skill check is a major part of developing the story at your table. This aspect alone affects games so much because this is how we determine success and failure of the players. So these should be taken seriously! How awkward is it when the 18 Strength Barbarian tries to open the pickle jar and can’t, but the frail gnome pops it open because of luck of the dice? Funny? Absolutely! But over time our players will see that their character living out their role in the story might get diminished because we are using dice almost exclusively to determine success rather than taking into account what our characters are actually good at. 

I ask myself these questions before asking for a skill check from one of my players:

1) Does it make sense for the character to fail this? Can I make it make sense if they do?

2) Am I breaking good momentum in the narrative if I ask for a skill check here?

3) Am I unsure if the character would be successful at this task? Or do I feel like they are pretty likely to succeed on this?

I try to sort out skill checks that would get awkward based on the answers to those questions so here are examples of why I ask those questions.

Awkward Examples

1) The party enters a room and I describe the contents: a table set for dinner, a desk, 5 chairs, three windows, and one is open. The ranger asks how many plates are set at the table.
This may be a really obvious example, but it would be weird if we had them roll a perception check and not know the answer to that question. I don’t want to make it make sense why they couldn’t count the plates or see them.

2) An example of this is best shown in a conversation between a PC and an NPC where a PC is building a case to persuade or intimidate the NPC. Sometimes, the arguments made by the roleplay of the PC are good enough on their own for the NPC to be affected. Either reward well invested roleplay, or have PCs roll their checks before they speak out loud and then have them roleplay according to their rolled check, knowing the outcome. This avoids hearing a very compelling argument to then have an NPC just ignore what they heard or deflate all of the tension in the situation.

3) This is my favorite category because I feel like it gives the right benefits to playing certain roles in the game. If the Barbarian is asking if they can drag a heavy object across the room to help the group and it doesn’t really impact the progress of the challenge or story, just let them do it instead of risking failure. “Yes, your character would have no trouble doing that, what is everyone else doing?”

Let your players be free to live out moments their character should be successful at without the fear of random failure. They are heroes! Not blundering dolts! 

Failure is not a Dead End

One final way to improve how you handle skill checks is what you do with successes and failures. I am going to expand on this idea a lot more in another post, but not every check is simply a pass/fail result that happens immediately, and if you expand your definition of success and failure to also include an amount of time, you will find that your story will flow more smoothly.

Often for me, the best equipped person in the party attempts the thing they should be good at and rolls something in the 7-14 range that is too low for the 10-15 Difficulty Check. But they should be the one who accomplishes this and it doesn’t make sense for someone else to just stack their attempt at it on top of what the other player has already tried.

When I asked for this skill check, I already knew I was going to have them succeed unless they rolled a 1. What I was needing the roll for was to see how long it was going to take them to complete their task.

So instead of the result being an immediate failure just to make another player roll until we get an immediate success, I will say that the character that rolled the too-low skill check is still working on the task and unsure if they will be successful. So another player cannot jump in to try it on their own. But they might be able to help.

Instead of making this “failing” roll stop progress and make a weird clunky opportunity for someone less skilled to succeed, their “failure” looks like doing this task in a longer time than they would have hoped for. What could have been done in 30 seconds is now taking 5-10 minutes Depending on the setting and what they are trying to accomplish, this could be an unfortunate hindrance to their plans, but it isn’t a closed door. And the story moves forward.