What I Learned From My First Skill Challenge

I was quite nervous about running my first skill challenge.  There isn’t really an old school analogue for skill challenges, so they felt quite foreign to me.  I wanted to make sure I was “doing it right”.  I decided it would be best to run the challenge via email in between sessions.  This would let me dodge the issue of having to extemporize when I didn’t know what to expect, and would also be a good way to keep the campaign fresh in my players’ minds throughout the week.

My first email to the group detailed exactly what was expected of each player.  I told them they were participating in a skill challenge, in which they would have to successfully use ten skills before they failed three times.  I informed them there were certain skills that would be more appropriate than others, and these would require easier checks.  I didn’t tell them exactly what skills to use, though I offered my young son’s character (skills picked ahead of time) as an example.  The players were to choose two skills, describe their character’s actions, and roll the checks to include in their response.

My players were very creative, and did an excellent job in their replies; they seemed to really be pushing themselves as far as the roleplaying aspects went.  As I had unfortunately expected, many of the skills they decided to use were not “primary skills” for the challenge as presented in the adventure.  This made the checks tougher, and as a result, the group had failed twice while succeeding eight times.

Now I was faced with a dilemma.  According to the adventure, they needed two more successes, or there would be additional complications in an upcoming battle.  Should the two players who failed try again, so they wouldn’t feel left out?  Maybe I should ask two who succeeded easily to use the same skills again.  Or, I could throw it back out to the group and let them decide.

I chose to let two players who had chosen “primary” skills to roll again.  They both succeeded, for which I was thankful.  I didn’t want the party’s first skill challenge to be a failure, as that would have been very frustrating to them this early in the campaign.  This decision felt heavy-handed to me, and I worried I was railroading them, but I thought it was for the best.  Paraphrasing the players’ emails, I sent the results out the day before the next session.  Here’s a quote.

The power-hungry Tekel felt that assisting the rabble was a waste of time, and instead devoted himself to study.  He used various tricks of scrying, drawing upon his knowledge of the arcane, in order to divine whether the Iron Circle would be using magic in the fight.  He was able to determine that a sizable group of dark adepts ride with the enemy army to Albridge.  By meditating and drawing upon his knowledge of history, Tekel recalled a familiar symbol, seen carved into a staff of one slain Iron Circle wizard.  This symbol indicates that the Iron Circle has ties to the foul devils who inhabit Nine Hells.  Sobering news indeed.  (OOC: Arcana and History successes.)

So, what did I learn from my first real skill challenge?

“Meta” gaming can be counteracted
I will readily admit that my presentation of the skill challenge was totally out of character, more about numbers and minutiae than about a natural extension of role-playing.  That bothered me, and I am certain that many other DMs are totally turned off by such mechanical talk.  But I had little choice in this instance.  I barely understand skill challenges myself, and wanted to make it as clear as possible for my players.  Being transparent with the requirements and expectations was a necessary evil.

But doing so dilutes the flavor of the game.  I countered this by requiring descriptions from my players other than “I’ll roll for Arcana”.  By adding to their descriptions, it was easy to develop in game results for their efforts.  Many have pointed out that skill challenges are really just combats in which you roll with different numbers.  Though I can see that point, a good DM can use collaboration and storytelling to make sure a skill challenge feels far different than a fight.

One “meta” aspect I felt strongly about was not sharing with my players what skills were required.  Instead of limiting their choices to the prescribed list of primary and secondary skills, they could choose those that they felt were best, not what I or the designers decided were best.  Keeping the players guessing about what skills to use is extremely important to running a successful skill challenge.

Let the players be creative
I was totally surprised by a few of my players’ choices.  They seemed more interested in using their highest skills than more appropriate skills that they were less proficient in.  One player wanted to use Stealth to steal enemy weapons, and another chose Athletics in order to teach the local farmers some martial arts moves.  I was glad this didn’t happen at the table because I really didn’t know how to proceed.

In the end, saying “yes” to the players won out.  I told my Thief that his plan to use Stealth was probably best run as a short solo adventure, but perhaps he could use his skills to help camouflage or find good hiding places.  The martial arts training was allowed with no modifications; even though it was a stretch, it was still in character and certainly flavorful.  The players both ended up failing their checks, but the group still prevailed.  If you don’t tell players exactly what skills to use, you need to be flexible when they come up with something you don’t expect.

“Repeated” skills can detract from the experience
Two players rolled against the same skills they had already used once when the group needed more successes after the first series of checks.  This bothered me; the way skill challenges are presented (as far as I can tell in my limited experience), primary skills can often be used multiple times.  I’m not sure if individual characters are supposed to be able to repeat skills or not, but if this indeed the correct interpretation, I don’t like it, for several reasons.

The first is story-based.  I have trouble seeing how, for example, a shaman can consult with nature for assistance, get a result, and then do the exact same thing again.  Or, if the paladin smooths things over between argumentative factions, how can he do it again?  Speaking from a purely role-playing prespective, it seems like multiple uses of the same skill are redundant and make little sense.

Stifling creativity also leaves a bad taste in my mouth.  If a player uses a skill successfully the first time, they will almost always choose to use the same skill again if they can.  They do not have to come up with a new way to solve the problem, they can just do the same thing again.  There’s no incentive to stretch themselves.  They’ll probably just ask how many times they can repeat it, plunging the conversation straight into “mechanics” mode.  I’d rather see players looking at other skills and coming up with new ways to use them, rather than relying on Diplomacy or Arcana for the umpteenth time.

Finally, exactly how is the number of times a skill can be used in a challenge determined?  Is there a rule for this somewhere that I have, in my ignorance, missed?  Arbitrarily decreeing that Nature can only be used three times, for example, seems quite random.  I think cooperation and creativity would both be improved if repeated skills were disallowed, though the overall number of successes required to pass the challenge would probably need to be decreased to compensate.

Skill challenges can be very tricky, especially for beginning DMs like myself.  Look around the D&D 4E blogosphere and you’ll see that even accomplished referees struggle with running them.  As with most changes to the game in 4E, there are  benefits and drawbacks to the system.  The key is to alter skill challenges as you see fit in order to best serve the needs of your campaign.


  1. I think the new rules for Difficulty Class presented in the Rules Compendium really clreared some things up as far as skill challenges go. If you have the book, it’s on pages 125 127. Or…


    Broken down quickly. Easy checks are skill checks the whole group has to use. Medium are meant for skilled characters, and Hard are meant for Specialized characters.

    In my home group, rarely does the 20th level minotaur engage in diplomatic conversation. That is left to the party’s bard/warlord, a specialized speaker. However, the bard/warlord can do little when it comes to physical activities. Climbing and bashing is left to the minotaur. The druid handles nature, the warlock handles arcana.

    The point is, often times your skill challeneges will be centered around one or two characters in your group. While annoying, this is also great because you can; a) easily predict which player the challenge is for, and b) react accordingly, to either hinder or help that person. I say, let that player shine for the night. Next week, a different player should be the spotlight.

    When DMing a skill challenge “on the fly”, it’s a lot easier if you know which character you’ll be reacting to (DMing is all about reacting). Think of the overarcing goal of the skill challenge; start with the end, then place a hurdle at the arbitrary halfway point geared toward the spotlight character.

    Think of a trying to sneak into a castle. Stealth is the obvious choice, but if you throw a moat around the castle, it becomes athletics. Bamboo chutes in the moat? Acrobatics. If you place guards, it becomes diplomacy. Giant turtles, nature. As the DM, you have full liberty which character hits the spotlight.

    Once you get comfortable with this, you can instantly weave a skill challenge into a story based on the characters, weaving each round into each skill set. I use skill challenges all the time, players just love to roll dice.

    To let them know they’re in a skill challenge, I’ve tried two methods. One is to make success and failure tokens. After any random roll you have them make in-game, you can give them a token without interrupting the role-playing. This lets everyone know a skill challenge is underway, without saying a word. The second method is what I use, it’s very similar. I just write either a “O” for success or “X” for failure on my board, rather than use tokens.

    Hope this helps. Personally, I love skill challenges.

  2. First of all, congratulations on running your first skill challenge.

    It was a good idea to run it via email. My first skill challenge was in a play-by-post game and I’ve gotten in some good practice for face-to-face challenges by running them online.

    Apart from using the latest DC table and success/failure ratios, and not using initiative (except when the skill challenge occurs in combat), I try to stick pretty closely to the model presented in the original DMG. That means that I don’t tend limit the number of times a skill can be used, unless it’s not a primary skill, or unless I “lock out” the skill for a particular reason. For instance, when the goal is to determine whether someone is in disguise, I required the PCs to make other checks to “unlock” the use of Insight.

    It _is_ boring for a PC to sit there doing the same thing over and over, especially if nothing else is going on (for example, I didn’t mind it that much when the wizard kept using Arcana to close the portal, because there was a combat raging at the time). What I try to do is greatly vary my description of what’s happening to try to prompt different approaches. In my last session, the party was trying to open an arcane door. Repeated Arcana checks would have done it just fine, but when I described how the door still wasn’t opening (after their 3rd of 4 required successes) I played up the fact that the doorway was old and pieces of it had fallen out of place. This prompted them to attempt some repairs, which I told them would be a Thievery check. Now, maybe I just have good players, but they went along with that, even though it wasn’t their best skill, and picked up a couple of failures before a clutch move by a PC got their fourth success. This challenge was also in the midst of a combat, incidentally.

    Something to remember when describing how a challenge evolves and responds over its course, is that you control the NPCs and the environment. Even “nature” is an NPC, and you can decide how it responds to your shaman, even if it still counts as a success. What if “nature” begins to lose patience with repeated hassling? Even if this has no mechanical effect, I bet your PC will start to wonder if he oughtn’t give it a rest (and this gives you a handy description for when the PC finally flubs one of his rolls).

    When a scene seems to call for diplomacy, it’s natural to want to keep using Diplomacy rolls and it’s understandable that these will get harder and harder to describe meaningfully. Some options: use the improv theater trick of making the scene about something other than what it’s about. The “diplomacy” is actually a cinch, but the hard part is understanding the historical and religious issues keeping the two parties at odds, while detecting the lies that they’re trying to slip in. Or, as with my example of the magical doorway challenge, have the scene take a twist. If it’s Diplomacy, Diplomacy, Diplomacy, have one of the disputants have (or feign) a heart attack. Diplomacy is still an option, but my bet is that someone is going to try to step in with a Heal or Insight check. As j0nny_5 says, you can decide which character gets the spotlight.

    He also has a good point about “starting at the end.” Make sure you have something interesting happen on both success and failure. In fact, make failure MORE interesting. Sometimes in stories it’s more fun when the characters DON’T succeed.

    I mention combining skill challenges with combat. I highly recommend this, as well as combining them with each other. Stand-alone skill challenges are, I find, pretty boring for everyone, even the people who have a chance of contributing to it. Instead of cramming in skills in order to make a single challenge more engaging (especially when someone’s just going to spam their best skill anyway) split it into two, or even three concurrent challenges, so that the PCs have to split up and maybe the second- or third-stringer in a particular skill will have to step up.

    I love skill challenges, too, in case you couldn’t tell. Best of luck with them.

  3. Thanks for the excellent replies. I’ve run two skill challenges since, and both seemed to go much smoother. I’m still not entirely confident in my abilities, but I’m sure this will improve over time.

    I think one key thing to remember is that every skill challenge is different. The two I just ran were entirely different in nature. One was more mechanical, as the PCs were piloting a magical flying ship through a blizzard-like storm. I was more “metagamey” foir this one, as it seemed natural. The masts of the ship got blown loose, and when the PCs asked what skills would work, I just told them. This kept the urgency and the pace moving along quickly.

    The second challenge was against the Winter King, the BBEG of the adventure. The challenge itself was more a structure for the roleplaying as the encounter began. I knew the PCs would fail at some point and he would begin combat, so by starting from the end (as Johnny 5 said) the whole thing ran better. Thanks again for your excellent advice.

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