Dungeons & Dragons Game Mastering

Challenging Skill Challenges

I really like the concept of Skill Challenges for non-combat encounters because they offer the opportunity to scale up a scene that would otherwise just be handled as a single skill check to make it more interesting.  Unfortunately, when I try to use skill challenges in actual games, I usually run into a few problems that have ended up impeding their usefulness.  I have some ideas that I’ve been implementing to try to solve some of these, but I want to start the discussion with just the problem statements before exploring the solutions that I’m trying.

Play Example #1

DM: The three leaders of the refugees are bickering amongst themselves, and none of them agree with your plan.  You’ll need to do something to convince them.

Player: [rolls dice] Okay, I got a 32 on my Diplomacy check.  Does that help?

DM: They’re willing to listen to what you have to say, but they’re not convinced yet.

Player: What?  That was an 18 on my roll…  Does anyone have a higher Diplomacy skill?

Other Players: No… nope, not me… no…

DM: Your check was successful, but maybe it’s just going to take some more work to convince everyone.

Player: Oh, it’s a skill challenge!  [rolls dice] Nice, 28 for my next Diplomacy check.

Introducing the Challenge

As that play example illustrates, skill challenges can get a little awkward right away because my players have a tendency to interpret any result other than a total success as a failure to hit the DC rather than as needing additional skill checks.  Some of this could be a result of our experience with previous versions of D&D before the skill challenge mechanic was introduced, but I have to hope there is a better solution than just leading with “This is a skill challenge.”

Mechanics to Actions

Another problem is that when confronted with a non-combat challenge, my players turn to their list of skills for ideas and immediately jump to skill rolls rather than describing what they want their characters to do.  In the example, the player just rolls a Diplomacy check and gives the result rather than providing any description of what his or her character is doing.

Sticking with What Works

Once my players have a success in a skill challenge, they tend to double down on the skill choice that worked rather than exploring other potential avenues to success.  Because each character has a different set of trained skills, this tends to lead to the next problem on my list.

Limited Participation

Where all of my players like to participate in combat, during skill challenges one or two players tend to dominate while the others sit back.  This isn’t always the same set of players, but instead it tends to be driven by which players have the highest bonus for a particular skill.

Play Example #2

DM: Okay, you guys are making progress through the sewers, but soon reach another intersection and need to choose which tunnel to take.

Player: Can I make a Dungeoneering check to try to figure out which one will get us out of here?

DM: Sure.

Player: [rolls dice] Darn, only rolled a 3.  I guess that’s a 13.

DM: Okay, you take the lead, but after a couple…

Player: Wait a second!  I was just trying to figure out which way to go.  I’m not taking the lead if I don’t know.

Measuring Progress

A complex skill challenge that takes the place of an encounter can require as many as 10 or 12 successful skill checks.  Where in combat, players get feedback as minions drop and monsters become bloodied, delivering progress during a skill challenge is a little more difficult.

Losing Interest

The length of complex skill challenges can also cause players to start to get restless.  While combat offers more structure and requires players to pay attention to other player’s actions for tactical opportunities, a skill challenge doesn’t offer much interest for a player who isn’t currently acting.  If dealing with limited participation, this can be an even bigger problem.

Risk Aversion

Once players know that they are in a skill challenge, they know that three failures results in them failing the entire challenge.  I think this causes my players to be extra risk averse and focus only on the skills where they have a higher bonus rather than exploring others skills that might be better suited to the situation.  This risk aversion also ties in with the next problem.

Failures of Knowledge

As the second example shows, knowledge-related checks can be a pain for me during a skill challenge.  The common way to interpret a knowledge check it that it determines whether the character knows something or in the case of a failure doesn’t know it.  This interpretation breaks from the skill challenge model though where a failure is supposed to have consequences.


Those are the main problems that I consistently hit when I try to use skill challenges in my games.  I have implemented some changes to how I run skill challenges to help with some of them, but for others I don’t have a good solution yet.  I’ll post the ideas that I’m trying later this week.

In the mean time, have you encountered similar problems, or entirely different ones, when using skill challenges?  If so, what changes have you made to deal with them?

By Scott Boehmer

A game enthusiast and software engineer.

7 replies on “Challenging Skill Challenges”

You raise some excellent points. Some time ago, I wrote an article directed at players about some of these same issues. Part of the problem, I think, is that players understand just enough about skill challenges to game the system (try to win), but not enough to realize they don’t have to and they are better off not trying. You might want to let your players see it: .

In general, after two years, I’m starting to come to the conclusion that skill challenges really aren’t for everyone and looking back at more free form approaches to non-combat encounters and challenges that I’ve used in past editions. Not saying they are bad, just that there seems to be no good way to get the mechanics to hide in the background so that players play the situation rather than the skill challenge.

I staved off this problem by explaining my players exactly how skill challenges work. I give them a reminder at the start of a session when I expect to run a complex challenge as a sort of forewarning and refresher’s course; I also remind players during skill challenges that they can contribute in other ways other than aiming for a success: aiding another and taking failures away. The latter is a new mechanic that I found lacking in Skill Challenges: I let a player try something to make amends for his or other character’s failures in the challenge, but I don’t tell him which skill to roll until the player tells me what he’s doing. A success doesn’t add successes to the challenge, but takes a failure away.

This is equivalent to a leader’s role who keeps defeat away in combat by replenishing his ally’s hit points.

I’ve had some of the same issues over the years. I’m a huge fan of skill challenges, but in my opinion they need a pretty flexible, varied approach, one that studies each challenge and decides how best to present the challenge — and which elements of a typical skill challenge to use.

In your first example, the diplomatic challenge, I’d encourage the players to do more than just roll dice — what arguments are they trying to make. Some players are not comfortable role playing a lot, so this might mean that they talk about it in the third person “Brak tries to convince the delegates that their debate only serves the powers of evil, and they need to find middle ground fast”. I’d encourage you, as DM, to throw around some +2/-2 modifiers for good and bad ideas, too — but make them do more than roll dice. This goes for those who are just trying to “assist”.

Diplomatic challenges are some where I tend to like to throw out the idea that every player should contribute in each round — that just seems sort of forced. But they should be encouraged by asking if they want to do anything, give them an opportunity, but don’t force the dwarf barbarian to talk to the king if everyone knows hes’ just going to swear and make things worse.

In your second example, navigating the sewers, there are a lot more ideas to explore. For one thing, it might be a good example to use an alternative to the “three fails” part of the system. What if each round of checks had a certain cost or risk associated with it, but the PCs could take as many rounds to navigate the sewers as necessary?

Knowledge checks might, on occassion, work like athletics checks to climb — fail by enough, and you don’t just know nothing, but know something terribly wrong (vampires have a debilitating fear of turnips!). Your players may need to role play some of these mistakes to make that work, but it could be fun.

Anyway, the already-too-late short version of my comment is to not see any of the skill challenge mechanics as graven in stone — they’re all base structure on which you can bolt exceptions, just like every other part of the game — and it’s in those exceptions that the Skill Challenge system REALLY gets interesting.

Can I make a suggestion on mechanics? Specifically regarding your mention on the trouble with Knowledge checks in a skill challenge, but i think this could be applied in a variety of ways.

Simplified, a skill challenge is essentially a series of skill checks that total up successes and failures, and are completed when a certain number of either are reached. But perhaps not all skill checks need to go directly to the skill challenge total. In the case of knowledge (and related to your specific example) – perhaps a successful knowledge check would give bonuses to the skills they did use for the challenge. Maybe even something like, +1 to checks per every 5 points of knowledge they roll.

Then, simply failing a knowledge check doesn’t randomly burn the players, and it could also encourage them to creatively to try to get bonuses and increase their chances of success in the skill challenge.

Just an idea.

@The Angry DM: That’s a good write up.

@Al-X: I agree that the new skill challenge mechanics introduced in the Essentials books add some nice twists.

@John: Encouraging my player’s to be more descriptive is something that I’ve been working towards, and I like the idea of providing a +2 bonus for creative descriptions. Getting players to go along with wrong knowledge can be tricky in play because they know their roll was crap and in some cases already know the info as players.

@Wolfie: My only concern with that knowledge mechanic is that it potentially takes away the use of knowledge skills towards completing the challenge.

Great post! I too have run into similar problems with my players but very quickly made it clear that no dice roll is just a roll.

I had the exact same happen as in your first example “Player: [rolls dice] Okay, I got a 32 on my Diplomacy check. Does that help?” I answered saying, “Potentially, what EXACTLY is your character doing with that great roll?” It didn’t take long before they got the hang of things and the Warlord was using a strength check to toss the flailing halfling Sorcerer into the air to frighten off the crowd that had gathered around them. She said, “Who needs intimidation when I have an angry Sorcerer?” The more creative they get, the more rewarding I try to be to them as well. 🙂

I do still have that one player that doesn’t “get it” and is just like your second example. It would be different if a player says something like “I take the lead and study the fork in the road”, rolls low on the dice and then says, “Unsure of which direction is the right way to go, I shrug and turn back to the party asking if they notice anything out of the ordinary.” That’s basically the same effect of your second example but when role-played out opposed to the defensive tone of “Wait a second! I was just trying to figure out which way to go. I’m not taking the lead if I don’t know.”

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