The following are a some rules inspired by Blades in the Dark1. These rules would be useful in any game that has the players performing lots of heist, though it could be adapted to any situation where the players are likely to get stuck in planning paralysis. As always, before making use of these rules make sure that the group wants to jump-start the planned event and avoid the pre-planning before making use of them.
Pre Job Rule
To begin with instead of having the players make plans and gather equipment that they may or may not need, start by having each of the players making either a notice or investigate roll. Each player then gets one special benny plus one per success or raise they get on the roll. These bennys are used to purchase flash backs during the heist.
Start of Job Rule
Have the players tell you how they are going to start the job. For example are they going to sneak in a window, pretend to be delivery agent, etc. Based on this decision determine the opening skill roll to set the scene. If they succeed they are in a strong position to start the job. If they fail they are facing some sort of opposition.
An example of this would be sneaking into a window to gain access to the house you are going to rob. On a success, you have climbed in the window and are ready to start moving to the score you wanted. On a failure, you have tripped an alarm and any guards in the house are on alert and looking for intruders.
When ever the players get into some sort of trouble, they can spend one of their flashback bennies to set a flashback scene. This scene doesn’t change anything that has already been declared can’t be changed by the flashback, but it can be re-framed.
An example of this would be due to a series of bad stealth rolls, the crew is discovered by the guards. One of the players could play one of the flashback bennies setting a scene where the crew was negotiating with these guards bribing them to look the other way during the score. As long as the interaction is successful during the flashback, then that re-frames the current scene from a combat to something where the guards just tell them to be quiet and continue on with their patrol.
There are some things that I am not sure about with these rules. I always want the group to have at least a few flashback opportunities, and that was why I set the number to 1 plus the number of successes and raises. The problem might be that this generates too many, so this might need to be tweaked to reduce the number given based on how it plays and even how pulpy you want the jobs to be.
Anyway, I hope these rules provides some value to others and as I make more use of them, I will post updates or extra commentary on them.