Make Mine a Challenge

Monday, August 10th, 2020

Your players announce the following ideas during play, maybe during Downtime, maybe in the middle of an adventure:

  • “I want to convince the head of the depository to give me a loan!”
  • “The queen is pretty lonely…let’s say I seduce her…I know! Maybe convince her to marry me?”
  • “The texts I need to complete this research are in the grand library in the capital? I want to go there to access them.”
  • “I’m going to punch this guy in the face for lying to me about his qualifications!”

How would you handle each of these ideas from a player?

For some of them you’d play out the scene and roll a bunch of dice, for others you would run an adventure where the character(s) face opponents and obstacles, fetch quests, battles and multiple feats of skill, and maybe others you’d just roll a die to see. We do this because we tend to think of role-playing games as working in a particular fashion. We get into a stylistic rut. We don’t deviate from a particular formula of “how you do things.”

So we fully play out encounters, we make multiple die-rolls and do back-and-forth in-character speaking with the DM and other players, and focus on discrete actions-and-responses, as if everything done must be a scene of improv theater with dice. You may think there’s nothing wrong with that — but “right” or “wrong” isn’t the point.

What if I told you there are actually four different ways to determine each outcome?[1]

  • Say Yes
  • Make it a Challenge
  • Make it an Encounter
  • Make it an Adventure

And that each of these methods are a perfectly valid way to resolve any of those situations?


  • Say Yes: if you feel the goal is something that the character could reasonably accomplish, if it’s in their wheelhouse or that they’ll eventually succeed given enough time (and they have the time), there’s nothing particularly interesting or compelling about failure, it allows the player to show off how cool their character is, or you just want it to happen, then it just happens, no need to roll. Let the player fill in the narrative details, or supply a few of your own.[2]
  • Make it a Challenge: if you just want to know yes or no about the character achieving a particular goal, there’s a possibility of things not going their way, if a failure could also be interesting or compelling, or the attempt is not something the character would normally be able to accomplish, then roll a die (or two, as needed) to see what the outcome is, and succeed or fail you and the player narrate the results.
  • Make it an Encounter: if you feel reaching the goal should involve more interactions, would be more fun with complexity and nuance and multiple die rolls, some give-and-take in options and outcomes, you want a lot of back-and-forth between the players and GM to see how everything turns out, and the situation is interesting and compelling to play through in detail, then you do that and find out what happens.
  • Make it an Adventure: if you feel the goal seems complex and will take a large investment in time, and seems fun-and-interesting to play through over a longer period, then add it to the list of adventures characters could choose to undertake, and run it as a full-fledged adventure with multiple locations, NPCs, treasures, and dangers.

A lot of times “just how you do things” can simply be…not fun. It can be boring for multiple people at the table, dragging out events or scenes that aren’t going anywhere important, or place an inordinate amount of spotlight time on one character just to resolve a trivial matter.

But we have tools in our gaming toolbox that can be used to avoid this situation, and to mix things around in play. These aren’t new tools, they are already in your toolbox, we are just explicitly naming them to make them more noticeable and so they can be more easily applied to multiple circumstances.

For example, Downtime actions already utilize these tools: Say Yes and Make it a Challenge in particular are both well-represented among the various actions available.

When a player chooses to have their character Work, we don’t play out the entire week, or make skill rolls, or work through the intricacies of farming and role-play the feud with the neighbors over that quarter-acre patch of grass — we simply declare the character has done it and they gain their weekly income. We Say Yes.

Train an Attribute is another example of something that could be run long-form, since it takes weeks of training, instruction, and interaction with a trainer, but instead we Make it a Challenge and resolve those weeks of effort with one or two dice.

You’ll note that despite my descriptive text of these tools above providing some loose guidance of when each choice might be most appropriate based on a character’s given goal, you should not take this to mean there is a set list of actions, situations, or goals that must be or should never be handled by one or more of these tools.

The great part of using this method is you don’t need to be tied to “should.”

You may in two similar circumstances Say Yes one time, and in the other decide it should be resolved as a Challenge. Sometimes a quick scene is a lot more fun than a full-scene encounter, or even a full adventure. Sometimes it is quicker and more suitable to resolve the same situation as a Challenge instead of as an Encounter, or to simply Say Yes. It simply depends on the surrounding context and your group’s preferred style of play.

If this “anything-goes” procedure seems weird to you, I am again going to reference that characters can already undertake adventures during Downtime, with the entirety of the adventure happening off-screen, and the results of the scenario handled by a single roll: Downtime adventuring is an example of Making it a Challenge regarding something that you might think could or “should” only be handled by Making it an Adventure. Neat!

This four-response method is very flexible. It’s very useful to have these other resolution options available when one character is off doing things on their own — after all, we should save the big, complex, full-engagement stuff for when all the characters are together, so we can be assured everyone gets their spotlight time. (As always, if your players disagree with your choice, or they want to — or don’t want to — play something out, discuss it with them and let them take the lead.)

Let’s jump back to our example ideas given to us by the players and see how each one might work in practice (though there are really multiple ways to resolve each, these are just examples of directions they could be taken):


“Sure thing! Given how much gold you were throwing around last month, the head of the depository is more than willing to give you a loan. What’s your Charisma? OK. The loan has a pretty standard interest rate and repayment date on it. He slyly suggests he can extend that date for a small fee…you get the feeling he’s asking for a bribe. No? He smiles and says to come see him if you change your mind.”

“The head of the depository is aware of your outrageous spending habits. But he seems, perhaps, amenable to loan you the money if you can convince him otherwise. How do you want to approach him? OK. Make a Charisma check, add +2 for your Guild status, and another +2 for your Intimidation tactic (that’s not going to endear him to you, though). Success!”

“So you chat up the head of the depository. No, he doesn’t know who you are. No, it doesn’t matter, there are rules. You can try, give me a Charisma check, but he’s not inclined to help you, so there’s a penalty. Sorry, that’s not happening. Sure, you can try to bribe him, give me another roll, +2 this time (you’ve found his weak spot: he’s a bit greedy). Fine, he’ll give you the loan, but he wants you to do something for him. Simple, really, he hasn’t had a break for lunch — get him a sandwich from the market. Going to do it? OK … Well, it was really that simple. He gets crumbs on your application, it smears the ink when he brushes them off. But you’ve got the loan.”

“He’s willing to give you the loan — but you have to do something for him first. It turns out there’s been a plague of rodents of unusual size in the lower levels of the depository. He needs someone to clear them out. You might want to bring friends. Oh, yeah, a few valuables stored in the depository have gone missing, and one of the junior clerks who was supposed to be taking inventory down there. If you can find and return all those, that would be great. And it’s probably nothing, but one of the other clerks who went looking for him said they saw a wall had…collapsed(?) and there was a dark space beyond that stank like the sewers. They were swarmed by a bunch of rats at that point and fled back upstairs. That’s when we locked the doors to the lower levels. So do you want that loan or not?”


“Sounds good! The queen is quite lonely, and your long service to her kingdom has endeared her to you quite a bit. Tell me about your relationship and the wedding ceremony, which takes a few months to plan — it is a royal ceremony after all! I am going to say you’ve made a few enemies at court who were rivals for her affections and you not being of noble blood yourself — the Baron of Shirress in particular. Mark him down as a new Rival on your character sheet.”

“You’re going to try to seduce and marry the queen. OK, let’s make that a Challenge…but if you fail, you might end up in the dungeons for offending her, so you can’t go on the next adventure, or you might anger a powerful rival also vying for her affections, who will make life difficult for you (and your friends). What’s your plan here? Cool, that sounds like it might work. Give me a Charisma check, +2 for romancing her that way, and since you’re friends with her steward, take another +1.”

“You know what? Let’s run through a scene where you meet with the queen and attempt to let her know of your…affection for her, and then we’ll work from there. … OK, so you’ve charmed your way past the steward, but you find the queen is already entertaining Baron Shirress, or perhaps he’s pressing himself into her company, you’re not sure. Roll to try and read the room? Nice. The queen is hiding how aggravated and uncomfortable she is, she clearly wants this audience with the baron to be over. You’ve picked up on it, but he doesn’t seem to have noticed. The baron, however, is clearly unhappy with your sudden appearance and interruption. Do you want to make your move in front of him, and offer the queen the jewels you brought, or wait for him to be dismissed first (or try to get him dismissed)?”

“Earning the queen’s affections is going to require quite a bit of involvement…sounds like an Adventure to me. I think you have to clear some wild lands so she can grant you a noble title first, unless you can find some way around that. Perform some feats in her name, maybe retrieve some precious jewels or artifacts? You’ll have to get close enough to her to make your affections known. Maybe you can manipulate the steward to give you an audience? And you’ll have to contend with other challengers at court who might…send a message for you to back off, either personally or with some hired muscle. Is everyone interesting in doing this? Awesome. What characters are helping out here? What’s your first move?”


“It’s about a two-week journey to the depository, but the empire keeps its roads secure — especially those running to the capital — and there are plenty of (generally) reputable traveler’s inns to stay in on the way. After you arrive and get settled, you pay the small patron fee for use of the library and get to work. Sound good? OK. Let’s get to that research roll and see how it pans out!”

“That’s a pretty long journey, and you’re both nearly broke and not used to planning for trips like this. Do you leave someone in charge to make sure your business keeps bringing in profit while you’re away (or at least doesn’t fold)? OK. You know he’s pretty reliable. The roads are generally safe, there are places to stay but you might have to camp out a lot, and that doesn’t mean there aren’t predators, human and otherwise, lurking about. Give me a Wisdom check to see if your plans work out, or if you arrive at the capital broke from bad planning, having been waylaid, or having abandoned your belongings to an unfortunate surprise encounter with monsters.”

“Tell me what you do to get ready for the trip? OK. Sounds reasonable. Let’s make a Wisdom check to see if you under-prepare. You’ve got a two week journey through fairly peaceful country, but at the third traveler’s inn you stay at, you’re awakened in the middle of the night by someone creeping around in your room, rifling through your belongings…what do you do? … And with that done, we’ll say you manage to get to the capital city without further incident.”

“The trip is pretty long, about two weeks. The roads are mostly safe, but that doesn’t mean there isn’t wild country between here and there. Maybe a chance for some adventure. Does anyone else want to go with, to guard their friend, or just to visit the capital? Alright, everyone aboard, then! It turns out something has been happening on the roads…they just aren’t safe. Your first clue is a slaughtered patrol of red-coats, the king’s own peacekeepers who are supposed to keep the roads safe. Someone is organizing the bandits… Yep, that’s the second traveler’s inn you’ve found either burned down, or empty and looted of every loose nail… Bandits! … Dire wolves! … You’ve found their camp! … SHOWDOWN! … You begin to wonder who was really behind this. The forge-mark on the crates of weapons shows they were crafted by a neighboring kingdom.”


“Your punch breaks his nose. He falls down blubbering and crying until someone drags him away. Next applicant! (You hope that guy isn’t connected with anyone…important…)”

“OK. You wind up to punch him, and yell at him about lying to you, but when you take your swing, it turns into a full-on scuffle. Make a Strength roll to see how it turns out, take a +2 for being a warrior, and since this guy turned out to be a wimp about his battle-experience, why not take another +1. Ouch. OK, you roll around on the floor a bit, trying to restrain him while he punches wildly…he manages to get in a cheap shot, knocking the wind out of you, and uses that chance to run away, calling you some rather foul gesture-accompanied names as races out the door. He’s vanished into the crowded streets before you can chase him down.”

“The punch turns into a full-on brawl. The entire tavern appears to have just been looking for an excuse to start throwing punches and chairs. Roll for initiative… You’ve managed to work your way through the brawl to where the guy is hiding under a table. He looks up at you, surprised and then angry. He flips the table to get in your way and makes a run for the back door… caught him! But the tavern owner isn’t happy you’re in his back rooms, and even less happy about the brawl you two started. He announces the city watch is on its way. Do you want to appease him, just make a quick exit, or make another enemy and start throwing punches at this guy, too?”

“Unfortunately, this guy was connected. In a bad way, for you. To some bad people. They hear about the incident, about you breaking his nose, and people come looking for you… You and your friends have finished taking care of these goons. Now what? OK. ‘Can’t make us talk!’ the one who must be the lead goon sneers. Let’s make some rolls, intimidation and such, see if you can find out who the boss behind all this is. Wow! Nice rolls! The guy spills everything. OK, you cut him loose and he runs off to tell his boss you want a meeting… Right, so you’re going to have to meet with this guy, who turns out to be the local crime kingpin, and you need to intimidate him into backing off (but that’s going to be pretty hard), or maybe you can convince him to get his goons to back down if you do a favor for him, or… Seriously? Alright. Who are you sending to do that? …Alright, after some serious negotiation, they’ve managed to convince the city guards to get involved and make a plan to take this kingpin down…


Of course, those aren’t the only ways to handle each combination of idea and resolution method. You could present the whole “clearing out the depository’s lower levels” as a Downtime adventure and resolve it with a Challenge roll, or as a couple of quick encounters, with you and the player narrating the pieces in between, instead of running a step-by-step dungeon crawl through the entirety, and so on.


[1] This idea is borrowed directly from Heroes of the Exploding Kingdoms, a game designed by some friends and acquaintances, currently in playtesting.

[2] There’s one very important rule about Say Yes: you should really always try to Say Yes about the small stuff when you’re not dealing with something really outrageous or against the spirit of the game or established rules of reality (but if your players are all mature and invested, this is unlikely to be a concern).

If you don’t want to “just” Say Yes about something, that’s what the other three options are for — they’re “OK, you can, but…” giving players the opportunity to make it happen without you having to say “no” and robbing players of their agency (remember, it’s their game, too, and their story!). You can always let them try, just make sure they know what the consequences of failure are.


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