Welcome back to The Anti-Rules Anthology. We have already sped up combat by fixing Initiative and removing tedious HP tracking. Now, we turn our attention to the moment-to-moment gameplay that often slows the game to a crawl: the skill check.
If you want your players to feel like the epic heroes they are supposed to be, you have to stop asking them to roll dice for every single thing. Our goal in this post is to show you when to give your players a guaranteed success, instantly affirming their character’s identity and keeping the story moving. This is how you master the D&D Skill Check.
The Problem with Rolling for Competence
The rule we are breaking is requiring a player to roll an ability check for every single action that uses a skill, such as Stealth, Persuasion, or Thieves’ Tools.
Constant dice rolling leads directly to the phenomenon of the “Incompetent Expert.” Imagine your Master Rogue, who has a +7 bonus to Thieves’ Tools, rolling a natural 1. Suddenly, they fumble a simple lock. Meanwhile, the clumsy Fighter, who rarely attempts social actions, rolls a 20 and becomes an overnight social genius.
This constantly undermines the player’s investment in their character’s background and core abilities. Why play a Master Thief if they fail to pick a common lock half the time? This constant need to roll a D&D Skill Check for everything slows the game down and makes success feel random, rather than earned.
The Goal: We must reserve dice rolls for moments of true consequence or extreme difficulty, letting characters shine in their areas of expertise without the randomness of the dice.
The Anti-Rule Solution: The Auto-Success Threshold
Our fix is the Auto-Success Threshold. This is a rule where, if a character’s skill bonus is high enough, they automatically succeed at a task with no roll required.
You still use the standard Difficulty Class (DC) tiers, but now they determine when the dice are needed:
| Difficulty Tiers (DC) | Example Tasks | Who Succeeds Automatically? |
| Trivial/Mundane (DC 10) | Opening a door that is not locked, picking a very simple common lock, convincing a tired guard to let them pass a non-critical post. | Any character with a +9 modifier or higher. |
| Standard/Expected (DC 15) | The typical task your character should handle (e.g., hiding in dim light, scaling a basic wall, haggling for a fair price). | Characters who are experts (typically +5 modifier or higher) on Mundane tasks. |
| Challenging (DC 20+) | Actions where a roll is necessary (e.g., hiding from an attentive guard in daylight, picking a masterwork lock under pressure). | No one. A roll is always required. |
Implementing the Auto-Success Rule
We use a simple check to determine if the roll is needed: If the player’s minimum possible roll (a 1 on the d20 plus their modifier) meets or exceeds the DC of the task, they automatically succeed.
For example, if your Rogue has a +10 to Thieves’ Tools, their minimum roll is 11 (1 + 10). If the lock is a Trivial DC 10, the Rogue simply succeeds. You skip the roll, affirm their expertise, and move the story forward. This is how you make the D&D Skill Check feel relevant only when it truly matters.
A Better Approach for Mundane Tasks
To improve D&D Skill Check consistency for all high-level players, simply grant automatic success on Trivial/Mundane (DC 10) tasks to any character with proficiency in that skill. The risk of failing something basic should be removed for a character built around that expertise.
When to Always Roll: The Three C’s
This Anti-Rule philosophy does not remove the dice entirely. It just reserves them for dramatic moments. The dice must always come out when an action involves one of the Three C’s:
- Consequence: The result of failure has an immediate, massive impact. This is where the story changes drastically. (e.g., falling 100 feet, starting a riot, alerting the dragon).
- Contest: The action is directly opposed by another entity. This is an active struggle. (e.g., a Grapple check, a Deception contest against a wise guard).
- Constraint: The character is acting under severe pressure or resource constraints. This adds risk to a normally simple task. (e.g., picking the lock while submerged underwater, trying to persuade a starving, panicked mob).
If the action does not involve a high-stakes Consequence, a direct Contest, or a severe Constraint, consider the Auto-Success Rule.
DM Dialogue and Implementation
This change is communicated best through your voice as the DM.
When a player asks to perform an action, instead of instinctively reaching for the dice, the DM asks: “Is there any pressure or immediate threat right now?”
- If the answer is no, and the task is basic for the character, the DM replies: “You are a master at this. You get it done perfectly and efficiently. What do you do next?“
This keeps the game moving, reduces frustration, and constantly affirms the player’s choice and identity. This is the heart of better D&D Skill Check management.
For more guidance on a DM’s role, you can review the official Dungeon Master’s Guide.
This framework empowers DMs to affirm their players’ skills and focus the spotlight on truly crucial moments. The Anti-Rules Anthology continues next week as we tackle the complexities of magic! We will dive into Magic Without Math: The Sorcerer’s Spell Pool.