My players have found themselves with an opportunity – to steal a shipment of magical weapons, denying the power-hungry mayor of Dulwich a chance to shift the balance of power in the town in his favor. The local guilds and he are at odds of late. The PCs have had some unpleasant personal experiences with the Mayor in the past, so they’re eager to strike back.
The Problem
Confession – I don’t think D&D, as a system, has much to offer in a heist situation. Most of the detailed rules, as we know, pertain to tactical combat. Most often, a heist is about avoiding combat! Stealth is important, but most of all careful planning is where a heist succeeds or fails. Planning a heist is the crux of the mission. Unfortunately, careful planning when players have incomplete – and often nebulous – information is at best nearly impossible. At worst, it turns into analysis paralysis. And there’s nothing worse than having an entire session devolve into a “prepare for all contingencies” checklist instead of, you know, playing D&D. Currently, my game is on Wednesday nights and budgeted for 3 hours – I wanted to get to the action as soon as reasonably possible. This dictated my prep strategy, and I hope you will find it useful in your game – whether you run a heist or any other adventure type for which you think D&D is poorly suited.
What Makes a Heist Fun?
First step was to really understand the essential qualities of a fun heist. Personally, I love a good heist movie or show. I’m a huge fan of Leverage, and it has a great D&D vibes. If you haven’t seen, I absolutely recommend it. But why is it fun? How can I make the game, at the table, feel like watching Leverage or Ocean’s 11?
I started, as we all do, with a Google search. There’s a treasure trove of information out there, and I just had to find it. I narrowed the YouTube playlist down to some trusted sources and videos that looked helpful. Not all of them ended up being as helpful as I had hoped, but I definitely learned something from each.
Basically, Heists have The Hook (we have that covered), The Plan (we want to sorta skip this part), Getting In, Complications, Getting Out, The Twist. These can all be broken out in to sub-parts as needed, sometimes they can mix together or switch places (maybe you have a reverse heist where you need to plant the MacGuffin instead of steal it!). I don’t want to overcomplicate this one – it’s not an end-adventure, boss-level scenario – so I wanted to keep it simple. And I really wanted to focus on skipping the planning. In my research, I learned about a very powerful tool for this – Flashbacks. Heist-oriented RPGs use this as a core mechanic, namely Blades in the Dark and Leverage (The RPG). In short, during the heist action, when the characters encounter a problem they can use a Flashback to explain how they would have planned for this specific issue! This absolutely mirrors what we see in heist shows and movies – flashbacks are integral to the plot. I found some good detail on how to use this mechanic at Roleplaying Tips. That post also mentioned another really important thing to remember – Soft Fails. During the heist, if you treat everything as a binary pass-fail (as most D&D skill checks are supposed to work) – everything will completely fall apart for the characters at some point. In order to make things feel “fair” and fun, as a GM you definitely have to exercise your partial-success and partial-failure muscles.
So now I have my overarching guide for this Heist – a basic framework of the heist, and a mechanic so that planning is targeted and in the moment instead of analysis paralysis. I decided that each character would get one Flashback to use during the heist. Then we’d roll a skill check to see how well they prepared.
In Part 2, I’ll go over the players and some specific resources I used to put some meat on these bones.
Header image “Thieves Guild” by Igor Solovyev
Busy Wyvern 
2 thoughts on “Let’s Build a Heist, Part 1”