Dungeons & Dragons Online

Skill Challenges as an Improv Tool

If you've never run a skill challenge in your TTRPG game, you might be missing out on an incredibly useful improvisational tool. Have you ever come across a situation in the middle of a session where:

  • The PCs attempted a complex task you weren't prepared for.
  • You weren't sure what skill check to ask for, or how to resolve a series of actions.
  • A situation seemed too important to resolve in a single roll.

A simple and narratively satisfying way to resolve these situation is to call for a skill challenge. If you don't know what they are, check out

on the subject.

Skill challenges are often touted as great ways to run cinematic planned sequences such as chases and escapes. While this is definitely true, I think they also have huge utility for unplanned sequences as well.

Skill challenges have a few key benefits as an improv tool: they are a simple structure which you can pull out at a moment's notice, the difficulty can be easily modified to suit the challenge at hand, they put the onus on the players rather than the GM and they can include the whole party.

A simple structure

When unexpected things come up in game, you don't want to have to come up with some crazy complicated way of resolving it. You also don't want to have to pause the game while you figure out what that structure looks like.

You want something simple that you can just drop in and keep playing!

That's why the skill challenge is so great for these situations. If you get to X successes, you succeed. If you get to 3 failures, you fail. The DC is X. Get the players to tell you what they do, and play on.

I'm going to use an ongoing example in the post, it will all be in italics.

They were only meant to be in the city to find information on a lost artifact. But as part of the council of their home country, they decide to go to the king of this strange land and negotiate a trade deal for the benefits of both parties. They think it will help ease the famine back home. As the players ask for an audience with the king, you scramble to think of how you could run this easily but not just make it a series of persuasion checks…

Tell the players that you'll run it as a skill challenge. They need X successes to succeed, three failures to fail. Then ask what they do. It's that simple.

Easily variable difficulty

There are two very easy ways to modify the difficulty of a skill challenge:

  1. Change the number of successes required to succeed. You can just make it 3 successes to succeed, 3 failures to fail and that's completely fine for most situations. But if you want it to be a particularly difficult challenge, just make it so they need 5 successes to succeed, 3 failures to fail.
  2. Change the DC of the skill checks. I would suggest a typical DC of 15. Raise or lower that if you want it to be easier or harder. You can also modify the DC on the fly depending on the feasibility of the task they are attempting.

By default, make a skill challenge require either 3 successes or failures to succeed or fail, at a DC of 15. Then modify as appropriate to the situation.

For the negotiation example, you might decide that since there is no existing relationship between the countries, negotiating a trade deal out of the blue won't be easy. You decide they need 5 successes at a DC15 to succeed, three failures to fail.

Putting the onus on the players

They say 50% of DMing is improvisation, so why not put some of that burden back on the players? By asking them to specifically describe what they do in each leg of the skill challenge, all you need to do is narrate the outcome of their success or failure:

  • On a success, narrate some kind of progress towards their goal.
  • On a failure, narrate something bad happening or getting closer to the failure state.

Obviously this is still improv but it makes it easier because the players come up with the seed for the outcome. You can essentially 'yes, and…' the players, building on their idea to narrate what happens, rather than needing to come up with the whole idea yourself.

When they party get their audience with the king, you ask what they do. The bard gesticulates about the benefits to both parties and how their iron ore is the finest in the land. On a successful roll, narrate the king nodding in agreement and commenting on their own iron ore shortages. On a failure, narrate the king frowning and commenting on their current surplus of ore; if the party had put in the effort to truly understand their needs then they would know that.


Resolving something in a single roll by a single player can not only be narratively dissatisfying but can also leave players feeling excluded.

In the negotiation example, without a skill challenge the bard will be the star of the show but what does the barbarian do in the background? Stand there silently while the bard makes that game-changing persuasion roll?

In a skill challenge, everyone in the party can contribute to achieving the desired outcome. In fact, I propose that you should actively encourage all party members to contribute relatively evenly. Since the skill challenge is an abstraction of a series of more complicated events then everyone can contribute to the success of the overall situation, rather than just the one person who is leading the charge.

In this situation, the bard does most of the talking so he does a persuasion roll. Meanwhile, the barbarian stands menacingly behind him, demonstrating the strength of their armies. The king would be unwise to refuse a trade deal without proper consideration. The barbarian makes an intimidation roll, also contributing to the success (or failure) of the negotiation overall.

So, here is your script when your players try something completely unexpected

OK, describe to me what your goal is in this situation.


OK, I'm going to run it as a skill challenge. If you get to X successes, you succeed. On three failures… well, you guys don't want that… Tell me exactly what you do.

Example from a recent game

My players were speaking with a lone modron who had been programmed to clean a city. The city had been abandoned for thousands of years but since that was its task, the modron continued and had been locked in this groundhog day situation for that entire time. I had the NPC offhand mention that he had a 'law cortex' which compelled him to follow the task he was given.

The part which I could never have planned for was that the PCs decided they wanted to do surgery on the modron to remove the law cortex so he could be free to make his own choices. Do I just tell them it can't be done? If I say it can, how on earth do I resolve that mechanically? What should I make them roll to perform surgery on a robot?

So I simply said to my players: "OK, since there are no mechanics for this, I'm going to run it as a skill challenge. If you get to three successes, you succeed. On three failures… well, we'll see what happens. Tell me what you do." I mentally set the base DC at 15 for each check.

The players then described carefully removing a plate on his back with a dagger (attack roll with dagger, rolled an 18; 1 success), searching inside his cogs for the law cortex (roll investigation, 23; 2 successes total), trying to enchant the law cortex with magic to give him free will (roll arcana, 11; 2 successes, 1 failure total, I describe the modron whirring nervously as the law cortex flickers and sputters), and finally the wizard decides to try to dispel the law cortex altogether (roll spellcasting ability check, 19; 3 successes!). The surgery succeeds and the modron now no longer needs to spend the rest of his life cleaning an abandoned city!

This was easy to run, fairly quick to resolve and I barely had to think of a thing! By putting the onus back on the players, they tell you what they are doing rather than leaving the improv work solely on your shoulders. All I had to do was narrate the outcomes of their rolls.

Hope this has been helpful, feel free to comment some situations below and we can discuss how they could be run as a skill challenge!


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