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How to Run Skill Challenges in 5E (DM’s Deep Dive with Sly Flourish)

I was a guest on one of my favorite YouTube shows, the DM’s Deep Dive with Mike Shea (Sly Flourish). We had a blast discussing Skill Challenges.

Topics we covered include:

  • How do we define skill challenges? What did they mean in 4E? What do they mean now?
  • What 3 tips do each of us have for D&D 5E DMS for running skill challenges?
  • How did they work in 4E, and what did we learn?
  • How should we run skill challenges in 5E?

I defined a skill challenge as a scene that involves multiple skill checks as the primary determinant for the action/storytelling. I think they are a natural evolution when you look at the arbitrary style of play before skills existed, and then the way 3E tended to focus skills on a few common skills (knowledge, diplomacy) that focused the action on a single player. 4E naturally tried to create a framework for cool scenes that involved the whole party.

Many of us today desire ways to highlight skills and test the characters in non-combat situations beyond one check. We want to navigate the wilderness, broker peace with the warring factions, solve the murder, and other such scenes.

Unfortunately, 4E’s skill challenges were not playtested well before release. Errata was quickly issued, but it still fell short both on the math of how they worked and in how they were presented. Skill challenges had a complexity, which could result in a ton of skill checks being required. And the idea of failure was just numerical, rather than situational. Consequences could be too weak, or too strong.

The format in adventures often dictated not just outcomes to the PCs, but actually told them what they did. (Athletics: You move a tree trunk to the wall and use it to climb up) rather than providing guidelines and allowing the DM to respond to the character’s actions. The result was a min-game devoid of much story, where every player found a thin reason to choose their best skill and quickly get a success.

When done right, 4E’s skill challenges were excellent. They involved every player in determining a story-rich way to surpass a challenge. We can do this in 5E as well. I listed my three tips as follows:

  • Focus on story and scenes, and less on skills.
  • Allow good results to provide advantages and move things forward. Failures are setbacks and complications that have a story/goal impact.
  • The whole thing should feel organic. Like a scene in a movie or a novel. Not like a board game.

For example, if our story goal is to put together a feast for the queen, we may have a few scenes. The market, the kitchen, and the dining room. In each scene, we may have various possible things the characters can do. Plus, we leave room for player improvisation. Cool ideas, spells, features, or similar factors could qualify as a success without a role. What we really care about is engagement. Failure isn’t lame, it’s interesting. So, for each scene, we think about what it means. If the group fails to overall get good ingredients, we progress, but we have a harder time in one of the upcoming scenes. If we do really well in the kitchen, we might cancel that earlier failure. It should all feel awesome, like a good story, and not like a dice-rolling exercise. The final scene in the dining room could involve some surprises. The queen demands a haiku, or a rival shows up. We heighten the stakes and see how it all plays out.

The final result can have a mathematical underpinning (maybe we decided in our design that they needed three successes in each scene with each character making one check, and maybe we decided that they must succeed at two of the three scenes), but as a DM we recognize any such design is arbitrary and the result should feel right. Importantly, we can change up what failure or success means. They might succeed, but they way they did so created a rival in the court or angered the people in the market. Or maybe they fail, but the kitchen staff will let them enter the castle through the cellars in the future. Results matter, but so do approaches.

I hope you enjoyed the DM’s Deep Dive. I’m a huge fan of Mike Shea and all that he creates.

Now, I’m curious. Can you think of any particularly great skill challenges in either 4E or 5E? Leave a message in the comments.

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2 comments on “How to Run Skill Challenges in 5E (DM’s Deep Dive with Sly Flourish)

  1. Shawn H
    April 14, 2021

    I found doing a skill challenge worked well with avalanches in RotFM. Given the lack of just about any mechanic at all from WOTC regarding them, a skill challenge worked well with the dearth of info. I used 6 passes before 3 fails. Each individual failure caused 1d10 bludgeoning damage and a STR or Dex save to determine if the PC was buried. Being buried triggered suffocation.
    Overall Group failure resulted in disadvantage on Investigation checks looking for any buried companions.

    • Alphastream
      April 14, 2021

      I like that kind of approach. And you are right… environmental hazards could have been an excellent way for WotC to have re-introduced skill challenges.

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