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Skill Challenges for 5E, Part 1

Skill Challenges for 5E, Part 1

In fast, fun combats, everyone participates! But combat is only one of the three pillars of D&D. Roleplaying and exploration sometimes lack that same zing.

Skill challenges are a great way to bring the same sort of structure and excitement of combat to non-combat encounters. PCs use different skills as a group to tackle what’s in front of them and achieve success together.

Note: Skill challenges in this series are adapted from the original concept in 4th edition D&D.


What Is a Skill Challenge?

A skill challenge is a series of ability checks undertaken by all PCs working together, trying to achieve a specific goal. PCs win if they reach twice the number of successes as there are PCs. They lose if they reach as many failures as there are PCs. (For example, 3 characters need 6 successes before they hit 3 failures.)

Running a Skill Challenge

You don’t need to plan every step of the challenge. To prepare, you just need to set a DC and know the stakes: what’s at risk, and what happens if the players succeed or fail. The middle part, the doing, is something the GM and players create together along the way.

Follow these steps to run a skill challenge. Each step includes tips on how to make the skill challenge really pop!

1. Tell players what they’re trying to accomplish. Why are they here? What do they stand to gain and to lose?

Tip: Break the narrative to explain the “game” of the skill challenge. It’s easier for players to imagine the situation if they feel like they understand the rules.

2. Announce the difficulty challenge (DC), the number that PCs must meet or exceed. It’s the same number for everyone, for all ability checks in the challenge.

Tip: A basic rule of thumb is to make the DC = 9 + the party’s proficiency bonus. You can change it for tougher or easier challenges, but when in doubt, lean toward too easy.

3. Players choose their initiative order instead of rolling. Encourage PCs with the highest modifiers to go first. Once they set that order, cycle through it, just like initiative.

Tip: PCs are significantly more likely to succeed if the character with the highest modifier goes first. Feel free to tell players this!

4. When it’s a player’s turn, they make an ability check with any skill their character hasn’t used yet in this challenge, even if it doesn’t seem to directly relate to the challenge. If their roll meets or exceeds the DC, mark a success. If not, mark a failure.

Tip: Work with a player to help create ways to use their character’s best skills. Let the whole group talk through how a skill can make sense for the situation.
Tip: A PC can only use a skill once in a skill challenge, but a different PC can still use that skill!

5. Regardless of whether the PC succeeds or fails, roleplay along with their action, what they’re doing, how it works, or how it doesn’t. Ask questions, and if they’re inclined, nudge them to talk in character.

Tip: Set up the next player by sprinkling hints into discussion with the current player. For example, if you know the next PC is great with Arcana, have the rogue taking their turn now find strange-looking runes when they Investigate. Do that regardless of success or failure!

6. The skill challenge ends in a win when players roll twice the number of successes as there are PCs. They lose if they roll as many failures as there are PCs.

Tip: Since the players know how close they are to winning or losing, use that in the narration of the checks. Lean into descriptions that make victory or defeat seem close.
Tip: Don’t make this challenge the only way to accomplish something the PCs need to move forward. In some cases, consider that they might reach the goal either way, but failing the skill challenge makes it cost more.

What to Use a Skill Challenge to Do

Skill challenges are great for giving structure to exploration and roleplaying.

In exploration-focused skill challenges, the PCs might:

  • examine and solve a puzzle before a trap activates
  • locate a secret entrance to a library to sneak in after hours
  • navigate through an inhospitable desert

These skill challenges give you a clear way to dish out information in a non-binary way. Rather than one player rolling a Wisdom (Survival) check and failing, then another player saying, “I roll too,” until someone succeeds, you tell a story along the way, revealing details using everyone’s strengths.

In roleplaying-focused skill challenges, the PCs might:

  • coax information out of a reluctant NPC
  • schmooze with subjects to find the weaknesses of their local baron
  • negotiate with a viscountess for better pay on the job she’s hiring them to do

These skill challenges provide a way to get all of your players to interact with NPCs, rather than just having the bard do all the talking . . . again.

Regardless of what you use skill challenges for, they nudge new players to roleplay their characters in a way that engage with the fiction and the mechanics. This can provide spontaneous jump-off points to play with, even when they fail their skill rolls. When the PCs search for the servants’ entrance to the red dragon’s cave, how exactly does Animal Handling help them? When they try to impress the hoity-toity nobles at a fancy party, what exactly do they Perform?

Upcoming Articles

This is enough to get you started! Next time, we’ll discuss planning for success and failure, mechanically and narratively. In later installments, we’ll dive into best practices (including how to respond when players try to break your challenge and more on some of the tips offered here). The final installments offer variations to keep things lively. I’ve been using them for six years and I’ve come up with a few fun tricks!


Find more ways to make your character unique and effective in Tome of Heroes. More than 20 new races and subraces, 70 new subclasses, new ways to use magic, downtime activities, and more! All playtested and ready for fun at your table!

3 thoughts on “Skill Challenges for 5E, Part 1”

  1. Thank you so much for this approach! I think everyone has been in the “they fail survival, let me try too” scenario. I’ve always had the feeling it ruins the pacing and makes such situations something nobody’s looking forward to.

    Thanks again, and have a good one 😊.

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