The Challenge Of Writing Skill Challenges

by Wimwick (Neil Ellis) on September 3, 2010

While attending GenCon this year I had a eureka moment. Or to be more precise, the sky parted, a brilliant ray of light shone down, I turned to Ameron and said, “We’re already doing that!” This was in response to almost every hand in the room going up in the air when Bill Slavicsek asked if people wanted more skill challenges during the Dungeons & Dragons preview seminar.

At Dungeon’s Master we love skill challenges. We enjoy writing them, dreaming them up and talking about them. Our archive has over 30 skill challenges and many related articles for the community to use and adapt for their own campaigns.

The challenge that comes with writing a skill challenge for a general audience is how do we make it specific enough to be important, yet general enough that anyone can adapt it and use it? It’s a conundrum.

As a DM, you know your own group of players. You know how to push their buttons to motivate or inspire them. Sitting on my side of the screen, I don’t know how to do that for your specific group. Of course I can imagine up a scenario that is engaging and has great meaning, but it is still up to individual DMs to take that and make it work with their own group.

In the past when creating skill challenges we’ve listed the primary and secondary skills. This is to aid the DM in knowing what our intentions are with the challenge and how to guide the players towards a resolution. However, it has the unintended side effect of making the skill challenge appear restrictive and not very organic. I’m a big believer that skill challenges should work towards moving the overall story forward, in other words there should be a point to the challenge. In my mind skill challenges that simply occur without an introduction are the best way to do this. Writing skill challenges for an unknown audience doesn’t always work this way.

What becomes more difficult is designing skill challenges for the paragon and epic tier. Simple negotiate or travelling skill challenges just don’t cut it anymore. The characters have advanced beyond this type of skill challenge being, well challenging. The characters participate in earth shattering, world defining, king making events by this point. As a result of the shift in character priorities it becomes more difficult to write generic skill challenges.

This leaves us writing more specific challenges. Less DMs may be able to use them, but hopefully those that do will be able to find a way to just drop them into their campaign. Our goal with the skill challenges we write is to have them be plug and play, as we look to write more specific challenges we hope to be able to maintain this type of flexibility.

Over the next month we aim to increase our library of skill challenges. You can still expect rough guidelines for what skills can accomplish what goals. Without this basic aid skill challenges would like the following:

Challenge: To convince the King to lend aid.

Success: You do it.

Failure: You didn’t do it.

Not very much fun. The goal of providing guides towards what skill will accomplish what is to make the DMs job easier.

Our aim over the next month is to broaden what skill challenges look like and how they can be accomplished. We’ll be releasing a skill challenge that features combat inside it. That’s right a skill challenge with combat, not combat with a skill challenge. In previous challenges we have also experimented with an alternate way to track success, and you can expect future challenges to have this mechanism in place, along with an article explaining the rationale.

A room full of D&D players told WotC they would like more skill challenges, I’d put good money down that you will see more content geared towards skill challenges in future Dragon & Dungeon magazines. We here at Dungeon’s Master have always felt that skill challenges have been under represented. What we would like to know are what kinds of skill challenges do you want to see?

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1 callin September 3, 2010 at 10:35 am

I have to ask. When people stated they wanted more Skill Challenges…was it because they don’t understand Skill Challenges and want more examples or because they enjoy playing in and running Skill Challenges?
I love 4E (I am running 2 separate campaigns right now) but detest Skill Challenges. I know part of that is my inability to run them effectively. I ignore them and simply do some role-playing and have the players make a couple of die rolls.

2 Wimwick September 3, 2010 at 11:45 am

@ callin
Great question and it is one that wasn’t asked. The feeling I got from the room was skill challenges were something they enjoyed, but they wanted to see more support for them. I think some want examples that they can just pick up and use, others want advice on how to insert skill challenges into the game. Our hope is to be a resource for both of those needs and I think to date we’ve done that. What we’ll be doing over the next little while is increasing our support for skill challenges.

3 Neuroglyph September 3, 2010 at 12:21 pm

I have to agree with Wimwick – I was in the room when the forest of DM hands sprouted at the Skill Challenge question, and I think DMs want to see more support for them. Plus, I think that many hope that adding more Skill Challenges to the content already out there means that there is a greater chance they (as a DM) can find a SC he can quickly modify for use at their own table.

I use Skill Challenges all the time, and often wing a basic Complexity 1 right under my Player’s noses. For simple ones like that, I just roleplay them out, calling for Characters to make skill checks after they have interacted with my “Challenger” and noting the successes and failures. Some of my Players pick up that they are in the midst of a SC, but others don’t realize it until I announce their overall success or failure. In my mind, if you can keep the transparency level low, Players enjoy it more than making an SC into a formal encounter (with initiatives, etc.)

4 anarkeith September 3, 2010 at 1:57 pm

Recently two of my players, who also run their own 4e campaigns, complained to me about skill challenges. In both cases they felt like “dolphins doing tricks for fish” or that skill challenges “destroyed the sense of immersion” when they were asked as players to craft more of the narrative.

I’ve challenged the players in both of my groups to narrate their skill usage, even to the point of inventing story elements to make it work. Some of them relish this. Others, as is evidenced above, do not.

I think there’s a lot of work yet to be done with skill challenges. I’d love to see more examples that I can use as templates for writing my own. A big part of writing a good challenge seems to be creating the details that you can reveal to your explorer-type players when they ask, while leaving the framework open enough to accept details your storyteller-type players provide.

5 QuackTape September 3, 2010 at 2:23 pm

I really enjoy skill challenges and, like Neuroglyph, use them on the fly nearly every session to help deal with diplomacy challenges or other random avenues that I didn’t anticipate the PCs taking.

My most successful skill challenge by far though was a skill challenge with combat in it. The basic premise was that the PCs were stuck in a small church surrounded by hordes of the undead (I know, quite original). In order to stop the plague of zombies, the PCs prayed at an alter to gain a unique super-charged turn undead. PCs without Religion though helped by barricading the three entrances to the room. I rolled each round to have the horde “damage” the barricades (removing a success from the specific barricade successes) and if a barricade broke, the undead (minions) poured in and had to be dealt with. Each undead in the room added to the Religion check difficulty so fighting them off was essential to keep generating successes on the turn undead portion of the challenge. When the divine spell finally went off, the players cheered in victory.

6 Lord Matteus September 3, 2010 at 4:19 pm

First, I want to thank the writers at this site for taking skill challenges so seriously. Indeed, your numerous posts focusing on the various skills available have been very useful to expand what was presented in the 4e PHB 1.

I have been DMing for about 20 years, but 4e is still new for me and I am trying to get a handle on the skill challenge. Soon I will be DMing a Dark Sun campaign with my old group (together again after a 3 year hiatus) and I want to ensure a good game while incorporating skill challenges. My problem right now is keeping them fresh and exciting. I look forward to reading your ideas and further content. Keep up the good work!

7 rednightmare September 3, 2010 at 4:31 pm

Up until now I have had mixed results. Some went great, I had to adjust on the fly to make them fit.
What I often find is that counting the number of succeses seems arbitrary, but that’s been said before on the site.
What I would like to see (because I plan on running one) is a heist skill challenge, mayby just as a information gathering before the actual heist (say breaking into the Sivis vaults)

8 Wimwick September 3, 2010 at 7:46 pm

@ Neuroglyph
I find skill challenges on the fly great. A difficulty 1 challenge is very easy to work into the game and it rewards the players with a little xp. As players become more accustomed to the mechanic it is easier to work in more complex challenges, seemingly on the fly.

@ anarkeith
Two things to try to help your players. Have them describe what they want to do rather than selecting a skill to use. After they are done describing the action, tell them what skill it is. Often players will say I want to use perception and then describe an action that is closer to insight.

Another thing to try is have them narrate their combat actions. Rather than having the fighter say I use cleave to attack, encourage the player to describe what their cleave attack looks like.

@ QuackTape
Great skill challenge, we’re, umm… well we’re going to use the idea you’ve described in a forthcoming challenge. It’ll be our take on it, but credit will be given where it’s due.

@ Lord Matteus
Thanks for the kind words. From the outset we’ve realized that skill challenges have not been given the attention they need considering they are a new mechanic for D&D. We’ve done our best to provide a resource for players and DMs so they can get the maximum enjoyment and benefit from skill challenges.

@ rednightmare
A heist skill challenge, I think we can dream something up. Thanks for the suggestion.

9 Volcanic Spider September 3, 2010 at 9:31 pm

I applaud your dedication to skill challenges. I anxiously await a library of new ones!

10 QuackTape September 3, 2010 at 10:07 pm


Quite all right! I’d love to see what you guys do with it. I never did a full write up on it since it was a hasty replacement to a multi encounter combat to “survive till morning” … which I had to come up with day of when I had trouble with my mapping program. It was fun to put the maps aside for a day though and worked really well; people got so into it I doubt they even realized that it wasn’t my original intent to play it out that way.

11 Jerrad Willis September 15, 2010 at 1:59 pm

Hey Wimwick,

I’ve had the same issues with my skill challenges. I’ve been using a very loose system of performing skill challenges using a 3 act system. You can check it out at

Maybe this could help you and others bridge the gap between open exploration and framed numbers.

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