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How Often Should We Roll Skill Checks, If At All?

Art from WotC; a bribe to look the other way.

D&D and other RPGs initially didn’t have skills. And some modern roleplaying games no longer use skills. Let’s look at the impact on play with and without skill checks and consider our own approach to how often we should have players roll them!

Interact and Ask

In them olden days, what we did was interact with the environment and ask questions. This had some advantages, helping to create improvisational and immediate play, really diving into the DM setting up a situation and then the back-and-forth as players interacted and perhaps changed something, and the DM responded.

However, this can sound better than it sometimes was. On the video version of this blog, I shared this room from the classic AD&D adventure, The Temple of Elemental Evil. (See the Best of Temple of Elemental Evil on Mastering Dungeons.)

The text has a lot in it, including a room with a partially destroyed marble chair, rubble and broken furniture, a high ceiling lost in the shadows, and the stench of rotting flesh. When we look at the text for the DM, a surprising amount of what is described to the players has no depth or import to it, and unless they specifically mentions they are doing something to examine the shadows overhead, 18 stirges will drop down and attack you! There is also a secret door, which has no interaction based on the room’s description, and a magic ring you might find if you somehow manage to qualify as carefully searching the floor.

That’s not a terrible room, but the information doesn’t really do much to drive interaction.

Let’s look at another example, from the Shadowdark adventure Hoard of the Sea Wolf King:

Shadowdark doesn’t use skills either. We get a somewhat shorted description, and the “leathery rustle” likely does a better job to invite questions and drive play. Of course, the obvious interaction is to lift up one’s torch to peer at the ceiling!

Why Skills Were Added to RPGs

Skills carry a lot of weight in 5E and many modern RPGs! They were perhaps added as a way for players to show expertise and develop their character. There is some truth that when we spend more time developing our character and deciding what our PC is good at, we become more invested in that character and probably in the game itself.

It’s worth pausing to ask ourselves, if we are a DM or designer, whether we are helping players realize this goal. Are we helping the Ranger feel like an expert in the outdoors? The wizard an expert in arcane matters? And, skills and expertise don’t just come from a class. Perhaps the cleric rallied a small town to oppose an enemy and are a Folk Hero as their background. Maybe the fighter, who we might think of as rallying troops, was actually a Street Urchin, so it’s really the cleric with that expertise. What about skills that don’t quite match the expected attributes? The fighter wants to intimidate and the cleric wants to know about the god depicted in the statue… but a Religion check is based on Intelligence and Intimidation is based on Charisma! Should we allow a better attribute to be used? Provide Advantage?

This is all worth considering when we think about the goal of skills in RPGs. We should also consider that skills have a gameplay role: that of clarifying and even codifying play for specific situations. In the AD&D or Shadowdark examples, we might see a lot of variance in how a DM will adjudicate a desire to peer into the shadows. One DM might say it’s an attribute check. Another might require you state what you are doing and require the attempt to meet some criteria, from simply saying you look to requiring you lift a light source high up into the ceiling.

Skills try to clarify this. Most 5E DMs would say that peering into darkness requires a Wisdom (Perception) check, perhaps at Disadvantage. If there are tracks to be followed or a chance of getting lost in the wilderness, some type of survival or wilderness lore check (depending on the edition and RPG) is likely to be used. Editions can vary, such as having a skill for Persuasion or Diplomacy or Streetwise, but for that edition gameplay becomes pretty reliable.

So, skills help us define our character and create reliable play, so we want to keep that in mind when using skills. We want characters to shine and we want to meet player expectations (most of the time).

Variants

Some RPGs have additional rules. In Gumshoe RPGs, including Timewatch and Night’s Black Agents, your investigative and knowledge skills represent deep expertise, so they always work. You don’t make any roll. The expectation for the game and any adventures is that you always succeed. Someone was murdered? If you have Forensics, you know how they died. This is because the clues should always be found in Gumshoe. The key fun is not if you find the clue, it’s what you do with it. And scenarios are written accordingly. You know this is stirge guano on the ground… now, what do you do with that knowledge? Do you attack the stirges? Do you draw an enemy here, using this as a trap?

We discussed last week how Daggerheart and Draw Steel, following games like Fate and Apocalypse World, don’t just have successes and failures. You only roll when there is something at stake and the result can include a complication or benefit as well as determining success/failure. This can make play very interesting, and adds improvisation, but calls on the GM to do a lot of adjudication.

Art from Shadowrun 3E

What is Success or Failure?

We mentioned previously that when we call for a check, we want success and failure to both be interesting. We want the situation to continue regardless of success or failure, and to be changed by which it ended up being.

Sometimes it’s very cut and dry. Can you make the jump across the pit or not? For a bit of granularity, failing by less than 5 might mean you grab the edge.

Other times, the result is less clear. Think back on the stirge or stingbat scenarios. Success might mean something less clear, depending on the approach taken. If we run either scenario with an RPG that allows for skills, we might decide success with Nature tells us the guano or the rustling is similar to bats, but different in some way. Success with Perception might glimpse one that seems to be sleeping, suggesting they would wake if disturbed.

One way to decide how much information to grant is based on the D20. A high result? More information! It’s easy for both player and DM to see that D20 and understand whether that’s a very bad result. We could instead use skill DC cutoffs, such as the recommended range for Easy/Medium/Hard as tiers where we provide more information.

Combine Skills and Engagement

Even in RPGs with skills, we should dissuade players from simply rolling. “I roll Perception.” We can respond with, “Okay, but what does that mean? What are you actually doing?”

The intent isn’t to punish (“You didn’t say you looked up!”), but rather to reward. “Aha! Since you are looking in the mud, you see there is a lot of guano that has fallen from above.”

Here is a set of criteria we can use to evaluate results on the fly:

  • What is the character doing? Does it help or hinder?
  • Who is the character? Does their background or class help?
  • What has been happening in the adventure so far?
  • Are any other factors making it easier or harder?
  • What did they roll?

For example, if the character is a Ranger with a background in cave exploration, saying they carefully check the mud, and they say they are using their sword to quietly stir the mud and look for anything in it, while keeping an eye on the ceiling? That sounds like success already! We might not call for a roll at all, or we might grant advantage and then on top of that be ready to provide useful information no matter what. “You only rolled a 10, but your background and your careful approach mean you see strange guano in the mud. It reminds you of bats, but it is different. You recall that bats startle when subjected to sudden changes in illumination or loud sounds.” If they had rolled well, they would know these were stingbats and exactly how they behave.

How Often Should Players Roll?

Let’s get to the heart of the matter. There is a ton of variance on this across DMs and, of course, some RPGs only care about what a PC says they do, with no roll at all.

This is also a question of style. The right answer is the one that produces great results at the table. If players are rolling to automatically bypass situations, or they are never explaining what they do, they are likely rolling too often. If players are bored, they might benefit from rolling more. Your game might work best when you save rolls for the most dramatic moments. Another person might keep interest high with lots of rolls.

Rolling has many benefits:

Rolling dice is fun! Players love to buy and show off their cool dice.

Rolling creates tension and draws other players in, as we all want to see the result. This can wake up other players, getting them to pay attention. Dice create drama this way.

Rolling can also serve as the climax, finally deciding what happens and releasing tension, whether due to success or failure.

Dice provide us a clear measure of how well the character has done at a task. This requires that we first have clarity on what the PC is doing and how, so there is high narrative interest. Dice also put results in the hands of fate and probability, instead of an arbitrary or arguable call.

Dice can help overcome a gap in player knowledge. Maybe they weren’t following when we said that the ceiling is covered in shadows and there is a strange sound. That die roll can be something we use to fill in the gaps. “You are examining the mud, but you rolled so high that you keep wondering about that shadowy ceiling. Hey, you hear something up there! A Nature check would tell you more.”

Using several skill rolls can bring several players into a scene. One PC might examine the mud, another the ceiling. When only some progress is made, such as rolling so low that they only find guano, this can create an opportunity to let a PC that also expressed interest make a second check and see what they hear up above.

This is especially useful in a situation like the stirge example. One PC might look for secret doors, another is investigating the floor, another the marble chair, and a final PC the ceiling. A series of skill checks can build tension and slowly fill in the details of the room. It is a lot of fun to start with the least important and end with the exciting reveal of something up above and a secret door.

When it fits your style and it is done well, rolling often can mean more players are paying attention, information is flowing freely, and players know that asking questions and engaging leads to die rolls and opportunity. Drama and excitement can be higher, with a sense of fairness rather than preordained results or arbitrary calls.

This ends my series on skills! Unless… maybe you have ideas for more to cover on the topic? Let me know below.

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One comment on “How Often Should We Roll Skill Checks, If At All?

  1. Sean H
    May 9, 2026

    I have a couple thoughts, not sure how much traction the discussion would get out of them. Primarily I want to talk about the relationship between Attributes*/Skills. If we look at a BRP d100 style game we see discrete skills. In some cases quite the list. I suspect this was an attempt at verisimilitude in design. A way to give more detail to the world or more discoverable detail. Boating, swimming, and running were each their own skill. Spot, Scan, and Listen were their own discrete skills. We see this to some degree in D&D 3E. Where we see additional similarity is that Combat, attribute rolls, and skill rolls all use the same die, if not entirely the same rule (there is no critical skill success is attribute or skill rolls.)

    Looking back to D&D B/X or BECMI we see that the only class that had skills were Thief characters. This is true in AD&D 1e, unless you count the Assassin’s Assassination’s table. In B/X you also had Ability rolls, which used the d20, and Perception(?) rolls which were a D6. Thief skills were a %, though you could roll a d20 and just do math (rollx5% = % rolled). Three different dice to resolve three mostly different aspects of the system.

    All of this to ask the question, what is a skill really? IS a Cyberpunk Tech’s ability to modify weapons a skill or a class ability? And how do you adjudicate the use of abilities versus skills? All rolls using one die seems like progress, but I can see some wisdom to drawing definite boundaries using dice as one example.

    Last comment, promise. Criticals are historically only for combat. Even in BRP where Special Success and Critical success are delineated, these are primarily for combat. Is that fair? Is that a system issue or is it a prep issue? Should we prepare content in a way to reward rolling that natural 20? Is someone more lying on a nat 20 than they are on a nat 19? As a designer do we need that answer? As a GM I think we do. I think its a boundary that has to be set, maybe expectation is the better word, that a nat 20 on a skill check does or does not deliver something extra, regardless of what the system says. In general a GM needs to be up front about what success gives a player.

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This entry was posted on May 7, 2026 by and tagged , , , .

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