Running the Heist
Now that everything was prepped, it was time to Do the Thing – run the heist. Immediately upon understanding the task at hand, the players started to plan. Within seconds – and many experienced GM’s can see this immediately – analysis paralysis started to form. Multiple players started trying to plan for every eventuality. I quickly cut off the discussion and introduced them to the new wrinkle here – the Flashback mechanic. When presented with a challenge at the table, during the heist, each player would be able to initiate a Flashback, wherein they explain how they would have planned for this eventuality, and what skill check they’d like to use to determine the level of success for their planning. Because this was an entirely new concept to my players, I was very liberal with the skill checks and the use of the flashback. The goal was to enable their success, their fun and make the heist feel like a cinematic experience. Whenever the players seemed a little stumped at a problem or a turn of events, I would prompt them with “Does anyone want to use a flashback here?” – sometimes they did, sometimes they didn’t. It was quickly seen as a useful tool in their toolbox, and not a gimmick – which was great!
Now this isn’t to say there was zero planning by the players – they did split the party, and have a general plan of attack – that discussion did take some table time, but it was certainly much shorter than your usual planning session. Overall, I think the flashback mechanic use was a huge success, and greatly facilitated actual play instead of spending time planning. The actual gameplay, other than the flashbacks, was very typical D&D – lots of silly mishaps, some gratuitous violence, a little NPC betrayal, confusion over what this weird glowing orb is (it was the burglar alarm, alerting the Captain of the Town Guard to the break-in) and even a natural-20 investigation roll, which resulted in a random magical item find. I used Vault of Magic from Kobold Press, for that too, and so a Frungilator appeared!
Conclusion
Running a heist in D&D just doesn’t feel right, rules-as-written. It’s simply not the best game for the job – but one simple tweak (Flashbacks) changed the whole dynamics. If I were running a heist-heavy campaign, I’d definitely use a more heist-friendly system, something designed around that core concept. But if you’re just doing a heist once in a while, don’t be afraid to steal mechanics from games designed around around it. And that goes for any sort of special operation you might encounter – as long as it makes things faster, smoother and – most importantly – more fun, steal mechanics from all over the place.
Have you run any heists? How did they go? Did you use any “foreign” mechanics, for better or worse? Let us know in the comments or hit us up @busywyvern!
Header Image “Escape” by gkb3rk
Busy Wyvern 
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