Skill challenges - gamifying the ungamified

Our heroes must infiltrate the Thieves’ Guild in the city of Waterdeep, and confront The Spider, the shadowy leader of the guild who has been undermining peace in the City and sending his goons after them. They have been told by an informant about the secret entrances to the web of tunnels under the Warrens, one of the poorer districts of the city, which lead to the Spider, but they must find their own way through this maze of traps and secrets.

They make it down into the thieves guild, and the journey begins. Hettie, the gnome Wizard, leads the group at first, carefully picking her way through the traps that litter the corridor, until she puts one foot wrong and triggers a trap. Arrows fly at the heroes from hidden compartments in the wall.

Next, Beans, the former Thieves Guild member, tried to use her knowledge of how thieves think to gain an insight into where any hidden doors might be. Unfortunately, her instincts lead her astray and she guides the party into a dead end. A portcullis drops behind them. They’re trapped, and they hear the footsteps of onrushing guards.

In a moment of remarkable strength, Eli, the Dragonborn Paladin lifts the portcullis, allowing the heroes to make their escape. Beans redeems herself by spotting a secret door nearby, and they slip through, just before the guards round the corner.

Aera, the Aarakocran Druid uses her spell ‘Find Traps’ to allow the heroes to pick their way through the next 120 feet of tunnels without any problems. The heroes arrive at an intersection. Eli uses his survival skills to find tracks leading down one of the tunnels, and leads the party onwards towards their confrontation with The Spider.

This is how a part of a recent session I ran played out. In game terms, it was just a series of ability checks, after which, the players reached the final confrontation with the villain of that section of the campaign. However, this series of ability checks was made more engaging to play by stringing it together into a skill challenge.

Skill challenges are a mechanic from 4th edition that I have been having a lot of fun adapting to my games. I recommend you watch the above video on Skill Challenges by Matt Colville for a rundown of the basics. I don’t intend to go over everything in that video again, but I do want to discuss why I like Skill Challenges so much, how I have been adapting them to my own purposes, and how I think Skill Challenges can be used to help you to improvise at the table.

Firstly, the basics. A Skill Challenge is a series of ability checks made by the players to achieve a certain goal. There is a set DC (I’ll discuss the DC I set below), and a set number of successes needed to pass (usually between 3 and 5). Generally, after three failures, you fail the Skill Challenge. Players can use any skill they can justify to complete the challenge, however they can only use that skill once.

Why I like it:

DnD is often described as having three pillars of adventuring - Combat, Exploration and Social interactions. However I don’t actually think this is true. Combat is where DnD becomes much more complex. As I discussed last week, the game hugely slows down when combat starts. It’s basically a mini-game.

There is nothing in the rules for an equivalent mini-game for exploration or social interaction. There are various skills for both, but one skill check with a pass/fail, is not a mini-game, Nor is it particularly robust or engaging, especially compared with combat. This is where Skill Challenges come in. You can create a mini-game which requires a series of rolls to succeed or fail. This could be exploration (as above), or even a social interaction.

Earlier in the same campaign, I used a skill challenge to roleplay an impromptu trial, where the players had to convince a lord of their good intentions in breaking into his vault. One persuasion roll in this case wouldn’t really suit, as it would not feel realistic to have the whole event hinge on one roll. Instead players were able to use their charisma-based skills to persuade and cajole, their wisdom/intelligence-based skills to spot chinks in the argument of others, or identify lines of reasoning that might have a greater effect, or even use dexterity-based skills to hide incriminating evidence.

Without a Skill Challenge, this above encounter would probably have been done just as an extended roleplaying sessions, we me having to decide whether the players were convincing or not, which is hard to legislate as a DM, and really takes the ‘game’ element, and therefore the character sheet out of the equation. Similarly, the first example above would have been a tedious dungeon crawl, where either I would have had to map out the entire maze and populate it with traps and enemies, or just ask for a series of skill checks with nothing stringing them together.

Skill Challenges help to gamify elements of DnD which are not currently gamified. A Skill Challenge does not have the same level of crunch as a combat encounter, but it does at least create a framework where players know how to succeed and when they have (or have not) succeeded.

How I run skill challenges

I use most of the rules Matt Colville outlined in the video above, however I have added my own spin to a few points. I use my range of success and failures taken from PBTA games, to make very high or very low rolls feel more significant than middling roles. I use a framework like the one below:

1-7 total failure - 1 failure and a severe consequence or complication

8-14 - failure - 1 failure and a minor consequence or complication

15-20 - success - 1 success

20+ - great success - 2 successes, or 1 success and an extra bonus (like finding treasure)

In the example I gave at the start, the first roll was a 13, so the players failed, and the consequence was triggering a trap which dealt some damage. The next roll was a 3, which resulted in the players being trapped and guards on the way (a much more severe consequence than a bit of damage), Eli then rolled a Natural 20, resulting in 2 successes. Beans rolled an 18 to find the secret door, so that was just a success. 4 rolls, each of the 4 cases above demonstrated.

What came next was the use of a spell, Find Traps. This resulted in a ‘free’ success, with no roll necessary. This is because the player has used a resource up. I could have just let this give Advantage, or maybe reduce the DC, but as it was a second level spell and the players were only level 4, I thought it was enough of a sacrifice to just give a success for free.

15 as the DC for a success may seem high. Matt Colville says 13, but I found that to be too low. Even at level 1, a player can reasonably expect to have a +3 in at least 1 stat. Add proficiency bonus to that, and most of the time, a player will be rolling with a +5 in a Skill Challenge. The average result on a d20 is 10.5, so players should just about succeed more than they fail. Add to this the possibility of 2 successes on a decent roll, and using resources or either lower the DC, give advantage, or get an automatic success, even if 5 successes are needed to pass the challenge, the odds are actually in the favour of the players. As players level up and get higher ability modifiers, higher proficiency bonuses, and more spells slots, the DC could increase, or the number of successes needed could increase.

Using skill challenges to improv better

Skill Challenges can be planned. Both of the ones above were planned, however I don’t think they have to be. Unlike combat encounters, they are not hard to adapt, or even create on the fly. It is on the players to come up with how they are going to use their various skills to succeed in the challenge. All you need to do as the DM is keep score, describe the players progress, and give consequences for failure.

Skill Challenges are quick too. If the target is 5 successes, you are going to be over in at most 7 rolls of the dice. That’s easily less than you get in even 1 round of combat. This means that they can easily be done when the party is split. I should have done this last week when DMing the same group. Eli and Beans split off to create a distraction so the players could escape Waterdeep in a ship. We did a series of skill checks to achieve this, but I did not frame it as a Skill Challenge, which meant it was less clear to everyone what was needed to succeed. What I did worked well, but a Skill Challenge would have framed the action much more effectively by making it into a mini-game.

Finally, Skill Challenges encourage us to think about failure slightly differently. In the example above, the players actually fail twice, before ever succeeding. If this were just a series of skill checks, it might be tempting to have guards arrive and fight the players, especially after 2 failures in the row. But they hadn’t failed the Skill Challenge yet. Had Eli been unable to lift the portcullis, they would have, and guards would have arrived, but he succeeded, and the players were able to keep going.

Despite those two failures, the heroes still made progress through the maze. In other words, they failed forwards. Despite failing, they were still making progress towards their goal. This may seem like it cheapens the failure, but I don’t think so. Both failures had consequences, and it was more narratively interesting that they failed, raising the stakes. This is key when running a session which has lots of roleplay or skill checks, as opposed to combat. Games which have more improv and are more free-form tend to be like that. Remember that you’re crafting a story together, not playing against the players. You want them to succeed. So when they fail it allows you to raise the tension, making the eventual success feel more significant.