Dear Gaming,

We need to talk about failed Skill Checks How we use them needs to change and it needs to change fast.

We misuse them and adventures grind to a halt because of a missed roll. We misuse them and cool backstory and details go missed. We misuse them and players stop looking for details because when they look in a smart way they are denied the most basic of information because of a bad die roll.

We could blame this on bad adventure design or too much backstory or players not dealing with failure well but I’d rather look more carefully at the easiest fix – the way we frame these rolls.

Examples

Thiefy McRogue, our example player character, has skulked through the shadows into the villainous Joe BBEG’s office with a combination of smart planning and a solid die roll. Guards are outside and about but none are in the office right now. He has no idea when Joe BBEG might return.

Player: I check the desk.

DM: Roll Investigation.

*RECORD SCREECH SOUND*

STOP.

No.

<< Rewind

Possibility 1

DM: What does that look like? What is Thiefy McRogue doing?

Player: Thiefy knows Joe BBEG likes to put traps into his desks. He hired those trap-makers back in Cool-ass Dragon City. I’m being careful to avoid those traps.

DM: Roll Investigation. If you succeed, I’ll tell you where the traps are and you can tell me what you do about them. If you fail, a trap is going to go off and shit is going to get real, there will be saves and we’ll see what happens from there. * rolls failure and failure again to avoid the dart and failure again to avoid the poison *

Player: Oh shit. Am I dead?

DM: Not yet. You know you have five minutes before the poison takes hold and you start to hallucinate your worst nightmares come to life. What do you do?

Player: Shit, I rampage through the desk to find those plans. Do I roll again?

DM: You rampage, you find them. The noise has alerted the guards and you can hear the alarm going up. You are starting to see things out of the corner of your vision, things your father summoned from the Far Realms when you were a child in his wizard’s tower.

Player: Shit, I’m heading out the window onto the roof (detail established earlier).

DM: You make your way to the roof and the guards are right behind you. Other things are following you and you can’t tell what is real and what is from the drug. Roll to see how fast you make your way across the slate rooves as the guards give chase.

Cool rooftop chase ensues…

Possibility 2

DM: What does that look like? What is Thiefy McRogue doing?

Player: We know Joe BBEG isn’t the type to trap his desk. I don’t care if he knows I was here. I’m quietly but studiously tearing this thing apart. I’m going to find those plans. I know they’re here.

DM: So you don’t care if he knows you were here and found the plans?

Player: I don’t have time to care.

DM: Cool, you find the plans.

Player: But I spent all these points on Investigation? Can I roll?

DM: Totally! Here’s the deal, if you succeed, you are going to find a detail that will give you an advantage die later to use on Joe BBEG. If you fail, maybe Joe will learn something about you and your methods based on how you toss the desk…

Player: Cool. * rolls success *

DM: Do you want to make up the detail that will give you an advantage in combat?

Player: That kinda fucks up my immersion.

DM: No problem, you find notes from a fencing class he’s taking. He’s studying the Devil Blade Style, learning from a Tiefling master who fought in the Devil-Dragon War back when the Tieflings made war on the Dragonborn, pawns between Tiamat warring on Asmodeus.

Player: And I’ll be able to gain an advantage die because I’ll be able to know what he’s going to do based on what I know about that fencing style.

DM: It was the same style your brother used as a Judicial Duellist in Cool-ass Dragon City.

Player: Shit, I know from previously established detail that the guards were going to change in a bit. I’ve waited too long and my safe route back is gone, yeah?

DM: Yeah, that is the cost of taking your time. How are you getting out of here?

Player: I’m going to walk out like I work here and try to bluff it.

DM: Roll.

Possibility 3

DM: What does that look like? What is Thiefy McRogue doing?

Player: I’m going to go through slowly and carefully. I don’t want Joe BBEG to know I was here. We know Joe BBEG doesn’t like traps so I’m not worried about that (detail established earlier, different than above so we can show a different example of failure).

DM: Roll Investigate.

Player: I’ve been putting all my points into that, training hard for this moment. * rolls failure * Shit, I guess I don’t find anything.

DM: You find the plans but haven’t opened the scroll yet when Joe BBEG walks through the office door. He smiles and says, “Thiefy, I thought I had lost you in Cool-ass Dragon City. I’m afraid I can’t allow you to leave with that,” and he’s clearly looking around, just a touch frantic to make sure your friends aren’t here.

Player: Oh shit, that’s right. Wizardly Mageman hit him and his crew with that Fireball in that fight on the docks. I act like Wizardly is invisible nearby, nod to him and yell, “Fireball now!” and use that to get out the window.

DM: You’ll have to jump through the window while it closed. No time…

Player: That is fine. I’ll take some damage?

DM: Yeah, a d6 or so. Roll your Perform Lies skill.

Player: * rolls a wild-ass success *

DM: Bahamut’s sack! That is a wildass success. You jump out the window and take * rolls * 4 damage as Joe BBEG dives for cover. He realizes the ruse fast, though and jumps out the window after you.

Cool rooftop chase ensues…

Get context and description of actions from the player before the dice hit the table, that way you can give consequences that make sense. What is at stake here? Is it a time crunch, getting this done before Joe BBEG comes back? Is it avoiding clever traps? Is it making it look like you were never here? That all depends on the previously established details giving this all context.

As the DM, I’m not looking for the rooftop chase or where this all is going. I don’t need to know the next steps. I don’t need rooftop chase to happen. I think it is cool but I’m not pushing for it.

I’m pushing for sharing details that give the NPC context and personality, give the players the information they need to move forward and offering consequences for the players’ choices. I’m not offering less details and cool shit because of failed rolls. I want to share cool shit. I’m offering consequences and danger.

In Possibility 1, Thiefy might get captured. That is cool. Saving a captured player character is a fun-ass adventure. Joe BBEG might not know how much they know and might have to change his plans at that point. We’ll see. If captured, Thiefy’s player can sit a game out (eh, not my fav) or play a helpful hireling or NPC.

Context, Cool Shit and Consequences at all times.

If the failure results of a roll are boring or not meaningful or stop you from making up cool shit or sharing cool shit, either technique is not being used correctly at the table or the game mechanics aren’t helping you, possibly a combination of both.

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