5e Skill Challenges

While I disliked many aspects of D&D fourth edition, I did like skill challenges. The following article outlines my conversion of that system to fifth edition. Credit where credit is due-this article draws heavily on the skill challenge chapter of the fourth edition Dungeon Master’s Guide II.

Choosing the Skills (and non-skills) for the Challenge
The short answer is, don’t choose any. Present the party with a problem or scenario and let them decide how best to deal with it rather than drawing a box of skills and secondary skills to confine your players, give them free rein to come up with a creative solution. Reward creative thought, award successes for non-skills too, for example if the players want to use a magical item, or a spell in place of a skill. Perhaps they bride the gruff city guard rather than try to use the persuasion skill.

Level of Complexity
Fourth edition used a five-tier complexity system for its skill challenges and I’ve reduced this to four to make it align better with fifth’s easy, medium, hard, deadly encounter scheme. Select a level of complexity from one to four. If your players are just poking about a small village trying to solve a crime, a one should do, however, if they are taking a voyage across a desert or sailing an airship to another country, perhaps a level four challenge is in order. Note: complexity differs from difficulty. Complexity only refers to the number of steps involved in the challenge, not how difficult those steps are. To be successful the players will need x number of successes before y number of failures. I’m using the patterns from fourth edition’s DMG2 where they refined the numbers published in the original 4e DMG.

Complexity Successes Failures
1                 4               3
2                 6               3
3                 8               3
4                10              3

Difficulty Class for 5e Skills/Ability Checks
Much like encounter creation, use a varying degree of difficulty for each step of your challenge. Lob a few soft balls (DC 10 – 15), and put a few challenges in their path (DC 20). Keep in mind that DC’s for skills are much lower fifth edition than they were for third and fourth. Without all those modifiers, the bar needs to be a bit lower. Gone are the days of fifth level bards rolling fifty on their perform checks.

Skill Difficulty Class
Very Easy 5
Easy 10
Medium 15
Hard 20
Very Hard 25
Nearly Impossible 30

Dealing with Failure
What if you players botch a roll or fail the challenge entirely? Failure shouldn’t end the adventure, it should just change the path the players need to take. If your players stealth through the prison but fail to unlock the door to the cell of the NPC they were sent to free, unlock the door but sound an alarm or alert the guards. Here are some ideas for failed rolls or failed challenges:

Possible Consequences for Failure:
• Increase the CR of the next encounter or raise the DC of the next skill roll
• Wandering monster
• Loss of a resource (Spell slot, per-rest power, hit dice, etc.)
• Apply a condition (poisoned, fatigued, etc)
• Inflict a curse or disease
• Expenditure of money or time
• Decrease an NPC’s attitude a step
• Disallow additional uses of that skill
• Damage
• Impose disadvantage on the next roll

Experience Points for Skills Challenge
Giving XP for role playing is a great way to reward RP, but it can be difficult to decide how much XP is warranted. I think the “XP Threshold by Character Level” is a good place to start. Try awarding each player XP based on the chart below based on the complexity of the challenge (1-4) and character level.
Xp Threshold

I hope this conversion helps you maintain a healthy balance of Role and Roll. I would welcome any feedback you may have in the comments section below. Please download the free, Boccob’s Blessed Blog 5e Skill Challenge Cheat Sheet below.

Final Thoughts
A good skills challenge should:
• Involve each player
• Use several skills
• Allow successes from non-skills
• Reward creativity
• Measure how well the PCs succeed, not if they succeed.

Skills Cheat Sheet

Would you like more free D&D 5e content? Download our free sampler from Limitless Adventures.  10 free D&D 5e encounters

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2 Responses to “5e Skill Challenges”

  1. I like this. A lot. The cheat sheet is printed and going into my DM folder of holding, along with some other gems I’ve found. This would have been particularly helpful for a boat race skill challenge I tried to wing in our 5e campaign last night! Better late than never. 🙂
    I would consider adding some kind of multiplier to the XP table for Skill Difficulty (much like the DMG has the Encounter Multipliers for multiple monsters. Maybe something like: Very Easy 0.5, Easy 1.0, Medium 1.5, Hard 2.0, Very Hard 3.0, Nearly Impossible 4.0

    • Thanks! I’m glad you liked it. I will look at the multiplier, that’s a good addition. We have a few other handouts you might like too – I find our name chart useful, as well as our Oh Sh!t Sheet. Thanks for reading.

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