Three Methods to Level Up Skill Challenges In Your D&D Games

Greetings, gamers from all systems, places, and timelines!

Skill checks are one of the fundamental mechanics of nearly any game system and always add the necessary randomness to the session; the results of the action are undetermined, even with the most mundane activities. You could be staring at the business end of a resounding success or a comical botch. However, some activities are best not resolved with a single roll to either save or suck. 

Why Skill Challenges?

Like myself, I’m sure many of you have been in a situation where a character in question needed to make a decent roll to move the story along, and it just didn’t happen, such as when the last three games were building up to getting a chance to ask the King for military assistance and then the person rolls an unmodified three on their Persuasion check. Instead of a single pass-or-fail skill check, something with multiple rolls and different abilities could be used to achieve success because of the situation’s complexity and the stakes involved. With that said, here is some advice surrounding Skill Challenges that we applied to our games, which could be modified to be used for one of yours.

18 Skills. Make Them All Count

While there are eighteen skills in 5e, many characters are only proficient with four, with two of these skills determined by the character’s class. Odds are, if you ran a Skill Challenge where the characters had to escape from a giant’s lair by climbing some vines, and you called for either an Athletics check or even a series of them, the party spellcasters will probably be shooting you dirty looks from across the table. Therefore, give them some options and assign all the checks to one DC or even different DCs based on what you have deemed as the best option in this scenario. 

Then come up with, say, three possible skills they can use. In the case of the vines, Athletics is an obvious choice. But you could also consider allowing them to use Acrobatics or Survival. You could take this as far as it makes sense in the scenario or even take a suggestion from the player on how they want to try and handle the task at hand. An example is if a character wanted to try and use their Perception skill to find the best vine to climb or even discover a different way to ascend to escape the giant’s lair. 

Structuring the Skill Challenge

Generally, four successful skill checks out of seven seem to work well. But there are some variables here. For example, you could have one person take the Skill Challenge or, as the situation dictates, have the entire party do so. In either case, you should have results ready for success or failure. For example, if a stampede of dinosaurs were chasing the party, passing the challenge would indicate that the character avoided getting trampled. At the same time, failure would mean they would receive damage accordingly. 

You could run a Skill Challenge with rounds to make things more interesting. For a more complex version, three to five rounds seems to work well, where the conditions of the Skill Challenge change from round to round or could even steadily increase in difficulty as the characters progress to the later rounds. For example, if you were running a Skill Challenge with four rounds in it, in the first round, the characters could make their skill checks at a DC 12 and then increase by one every round. 

Using More Than Just Skills in a Skill Challenge?

For any of you who have met me, the answer is a resounding yes, but hear me out. In Bonnie’s birthday game, I ran a layered Skill Challenge with five rounds where they were falling down the Rabbit Hole of Alice in Wonderland fame. During one of the Skill Challenge stages, the characters were attacked by a swarm of flying clocks. Now, I could have dropped them into initiative order, but instead, one of the options was to make at least four out of seven successful attack rolls to fend off the swarm or take damage. This worked well and spared me the joys of creating an entire stat block for a one-time use monster. 

Likewise, when my party was traveling through a poisonous marsh at one point during a Skill Challenge, one of the options was to make three out of five successful Constitution Saving Throws vs poison.  In another situation, the players needed to escape from a rapidly sinking ship when they were below deck. Instead of trying to swim up the stairs during the skill challenge, the mage wanted to use a spell to blast through the ship’s hull. Now, I could have calculated the hit point value of the hull in relation to the damage of the spell. Instead, he was just allowed to use Arcana to attempt to clear the Skill Challenge. 

Final Thoughts

I lean on Skill Challenges heavily during my games because they tend to add more to an important encounter than if it had been cleared with one lucky roll or derailed with a poor one.

Or even in some Skill Challenge scenarios, you could set a DC for a Skill Challenge and then ask your players who they want to try and handle it. Just keep the results of a failed challenge interesting but not catastrophic. Aside from taking damage, they might also find themselves with a level of exhaustion or even the poison condition for a set amount of time.  

The Skill Challenge mechanic is one of the gifts that we got out of the 4th edition of the game and one that can be entirely customizable for all types of encounters. Be creative and play around with different ways to use them in your games, and you might be surprised at the results. Skill Challenges change the script of “Roll Initiative” and add another layer of player agency to your games.

How have you used Skill Challenges in your games? We’d love to hear about it!