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Skill Challenges for 5E, Part 5

Skill Challenges for 5E, Part 5

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.

In all three pillars of D&D—combat, roleplaying, and exploration—the more player interaction the GM can bring in, the better. Players feed off of each other, naturally making bonds between their characters that you could never force them to. Like when the cleric saved the gang with a lucky 20 after the fighter and rogue almost talked their way into a bar fight. Or that time the warforged powered off in the middle of a negotiation, leaving the barbarian to do the talking.

This entry offers ways to make skill challenges even more collaborative by linking individual successes. The team already succeeds or fails as a group, but these ideas can really make characters work together.

If this series is new to you, go to the beginning to catch up!

Collaborative Twist #1: Combined Trials

Main change: Two players make their checks at the same time, and their combined results are compared to a high DC.

Suggested use: Pretty much any time you want characters to have to work together on anything.

In a traditional skill challenge, everyone waits their turn, as they do in combat encounters. What one character does has no bearing, mechanically, on the success or failure of the next.

But what if characters have to succeed together? To set up this kind of skill challenge, establish a standard DC, then double it. Characters must work in pairs, each making a check and then combining both of them. If the total is equal to or higher than the doubled DC, it’s a success! If the combined result is lower, it’s a failure.

For example, if the characters try to track a mythical creature across a hostile desert, they might need to rely on each other for strength and courage. The barbarian might shield the cleric during a sandstorm using Survival, while the cleric uses Arcana to look for evidence that the creature passed by. The better the barbarian protects the cleric, the easier time they’ll have finding those traces. Meanwhile, the fighter and the druid might both use Nature to find a safe path through the elements. Narratively, that could mean they talk things out between them.

An advantage to this twist is that checks become conversations and stories. Instead of a player saying, “I use Nature to try to find a path. 23. I find it,” players now must build off another character’s success or failure to explain what happens. If the druid rolls well and the fighter rolls poorly, does that mean that the druid’s on the verge of figuring it out when the fighter starts confusing things with bad ideas? Or if they succeed because of a great roll from the fighter and a so-so roll from the druid, does that mean that the druid’s stumped, but something they say sparks an idea for the fighter?

After each pair makes their checks, switch up the groups. Let players get a feel for telling stories with everyone at the table. If you have four PCs in the party, every possible pairing takes six checks—a very manageable skill challenge!

Collaborative Twist #2: Spotlight & Support

Main change: One character makes checks with a DC dependent on the other characters’ performances.

Suggested uses:

  • a rogue tries to sneak in somewhere that’s heavily guarded
  • one character is the lead negotiator

In a traditional skill challenge, every character is equal. But as one of my players asked a few months ago, “Wait, if this is about getting something out of the king’s room, let’s just send the thief!”

Sometimes, it makes sense to put one character in the spotlight and have the others support them. Like the previous twist, this is a collaborative skill challenge, where you set a DC and double it. But a single spotlight character is involved in every pairing along with a supporting character.

To run a challenge like this, a supporting player makes an appropriate check. The result they get is subtracted from the total DC. The difference becomes the spotlight player’s DC for their next check.

For example, the rogue tries to enter the king’s bedchamber, while the other characters must distract the guards. With this twist on skill challenges, the rogue repeatedly checks Stealth, and the other PCs occupy the guards using their best skills.

A big difference for the spotlight character is that they can use the same skills repeatedly. Narratively, this makes sense because the spotlight character is performing a single task, so they’ll be spamming that skill. Mechanically, it’s important because they’re almost guaranteed to make more checks than they have proficiencies. You don’t want the spotlight character scraping the bottom of their proverbial barrel when you’re putting the pressure on. Give them the best chance of success!

This twist brings tension and excitement that comes from the spotlight character knowing their DC going into the roll. And because those numbers are so dynamic, the spotlight character can play off of them in interesting ways, narratively.

 If the rogue sees that the guards are rapt by the bard’s story, they can describe bigger risks in their description. If they see that the cleric’s droning diatribe about the weather fails to engage, the rogue might look for a shadow to hide in—even if there’s no mechanical difference between those two stories.

Twist on a Twist: Support Sets Stakes for Spotlight

Main change: As above, but rather than establishing a DC, supporting characters’ checks determine whether the spotlight character’s success or failure counts normal or double.

Now let’s get weird with it. To start, the GM creates a range of DCs for the supporting characters and a fixed DC for the spotlight character.

When a supporting characters makes a check, compare it to the DC range. If the supporting character rolls:

  • within the range, the spotlight character makes their check as normal.
  • above the range, the spotlight character earns two successes if they succeed at their next check.
  • below the range, the spotlight character earns two failures if they fail their next check.

For example, the bard is the lead negotiator for a contract with a countess, but other party members are there to demonstrate their skills as needed. The DM sets the supporting party’s DC range at 12 to 18 and the spotlight bard’s DC at 15.

Narratively, the barbarian uses Athletics to display her strength. She succeeds! The bard explains how the party is worth more than this surprisingly low offer given how strong the team clearly is—as the barbarian smoothly lifts the negotiating table with one hand. The bard succeeds at a Persuasion check, and the team gets two successes.

Next, the wizard wants to impress the countess with his magical knowledge. Sadly, he fails his Arcana check. The bard explains how smart the team is . . . only to have the wizard accidentally spill components on the floor. Still, the bard rolls well for Persuasion, getting a success and preventing two failures by explaining that the wizard is so busy thinking that he forgets about his hands. That’s why they leave dexterous work to the rogue, assures the bard.

Alternatively, to make checks more dynamic, instead of changing the outcome, the supporting characters’ checks can determine whether the spotlight character gets advantage or disadvantage. If the supporting character rolls:

  • within the range, the spotlight character makes their next check normally.
  • above the range, the spotlight character gets advantage.
  • below the range, the spotlight character gets disadvantage.


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!

about Doug Levandowski

Doug Levandowski (he/him) is a freelance game designer and writer from New Jersey. His work includes all of the Kids on Bikes RPGs, a bunch of weird little indie games you can find on itch.io, and, most recently, Home. His ideal rules for a game would read, “Tell a story with friends. Use dice if you want.”

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