The Five Types of Challenges

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Engaging your players in TTRPGs.

One definition of a game is that games are a “voluntary effort to overcome unnecessary obstacles” (Bernard Suits), and while tabletop roleplaying games have a designated role for creating obstacles – the game master – it’s really easy to stare yourself blind on using the mechanics on the character sheet and call for a roll. However, rolling a piece of plastic is all but a challenge for the character, not the player. The roll can be exciting because the character or its goal is at stake. But it’s not a challenge per se. So imagine a system where all rolls automatically succeeded, and what kind of design solutions can come out of that premise.


Descriptive Challenges

How do I reach [these goals] with [these tools]?

A tabletop roleplaying game is nothing more than dialogue, where the setting, the situations, and the characters decide what you talk about, and the mechanics of how the participants are talking to each other. The result of this dialogue is fiction.

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By leaving out mechanics that are self-explanatory, in how they are used within the fiction, the game forces the player to contribute to the fiction by describing the character’s action to “build a bridge” between the mechanics and the setting.

  • The game shouldn’t have Lockpicking, but instead Resourcefulness. You use Resourcefulness to get past the locked door by lockpicking it.
  • Instead of hit points, restrict the player in how they can interact with the system. They can’t cooperate with others, can’t spend a certain type of resource, etc. It’s up to the group to describe how this restriction takes form within the fiction.

The weirder the tools, the more creative the players need to be in order to motivate how they are using the tools to accomplish their goals.

Exploring Challenges

How do [this thing] connect to [that thing]?

As the characters move in the world, a response should be to learn more about the setting. Mysteries are all about discovering connections between different factions within the adventure. As the players find out more about the mystery, they need to decide what to actually do with the information. In order to reach this phase, the game master needs to “reward” whenever the players are taking action, by constantly giving out more and more information until the players can form a clear plan of what’s going on.

  • The game master “peels the onion” by first revealing rumors and half-truths and then more and more truthful details, as the players explore the topic more. Factions that seemingly don’t belong together have things in common.
  • The game master is running several storylines at the same time, and it’s up to the players to connect the correct pieces to the correct storyline.

When playing like this, you want to create an overload of information instead of being restrictive. The problem shouldn’t be if or how the players find out, but what they do with the information.

Colliding Challenges

What should I choose between [this] and [that]?

As the world gets more populated by the game master, there will pop up factions with their own agendas. Intrigues are played out by giving several factions plots or agendas that the characters will collide with while they are moving toward their own goals.

It’s also possible to have conflicts within the group of characters, and even two conflicting traits for the same character. By having a lot of agendas and values collide, it’s possible to create challenges for the player.

  • Batman is a typical example of someone who has maxed out all stats, but he can’t rely on his Resourcefulness if he needs to choose between getting the Joker or saving passengers on a ship.
  • Create a McGuffin that a couple of factions want, each for their own reasons. Give the McGuffin to the characters.

The important thing is to ponder about the consequences of the players’ decisions.

Resource Managing Challenges

How do I use [this] in the best way possible?

Bookkeeping isn’t sexy in itself but can lean into creating interesting decisions. Note that resources here are more than hit points, equipment, or other mechanics on the character sheet, but time, information, people, status, relations, and much more. Every single thing in the world is a resource.

  • Set up conflict where there are several goals to achieve. Taking damage, protecting others, time-saving, different types of information, etc.
  • Make use of loss aversion, where people hate losing what they own. So give it to them first, then threaten to take it away.

Set it up so they can’t keep it all, but also give them enough information so they can make a decision. It’s not a decision if the player can’t know if the resource will be used in the future.

Portraying Challenges

How should I react to [this situation]?

To act upon or portray a character is something that comes with creating a character for a player. The player could challenge themself by taking on difficult character traits or others can create situations for them. What is different with this type of challenge is that it will add another layer on top of all the other challenges. Players can ignore this, and that’s fine if it’s not in their forte, while others thrive to act out in character.

  • Character secrets might create agendas, but if the other participants know about them, it’s easier for them to create situations where the secret will be endangered.
  • Have discussions between the sessions about the characters. Where they want to go, any changes the players can imagine the character will go through, or how they changed based on what they have been going through.

Don’t give mechanical rewards for portraying a character. Give them situations where they can act out their characters. That’s a reward in itself … because it’s fun.


If there is one thing that you should take away from this article: the conflict itself isn’t the interesting part but the consequences of that conflict. How people solved the situation, and what will come of that. That’s how you should design to overcome the problem with a system where the characters always succeed.

Note: there are even more challenges. These are merely the ones I use.

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