Session Planning in Role Playing Games

Some game masters love spending hours preparing and crafting adventures for their players. Some like to just make it up as they go, trusting their ability to improvise. Over the years, I have landed somewhere in the middle. I do enjoy some planning, but I rarely have the time to create elaborate maps and complicated encounters. I am comfortable spending twice the amount of time prepping for a game session than I plan on the session running, but that time is spread out over many days.

Rolling Initiative

Getting started can be tricky. You probably either have too many ideas and you can’t figure out how to organize them, or you don’t have enough ideas and you can’t seem to find any inspiration. I’ve recently returned to a Dungeons and Dragons campaign that had been on hiatus for nearly two years. I was surprised that people were still interested in coming back to that story and those characters, but I was just as happy as they were to do it.

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I had used the Game Master 5th Edition app from Lions Den on my iPad mini to build encounters and run combat, but I wanted to move away from anything digital. There’s something about writing stuff down on paper that I think helps my creative process.

I went looking for some inspiration on making that transition, and I found this video. I liked how he talked about jotting down ideas whenever he had the time, and I liked his use of plot webs. He also has a TWSBI fountain pen just like mine, and he uses a cool notebook. I still love using Moleskine notebooks for my planning. I then revisited Never Unprepared, Phil Vecchione’s great guide to session prep.

One of the most important concepts from Never Unprepared, at least for me, is identifying your strengths and weaknesses as a game master. For example, I know that it’s pretty easy for me to describe a location or a monster without a lot of resources. On the other hand, if I don’t prepare a list of names, then everyone is likely to be named Roger Elfdude or Bob the gnome. When I prepare, I need to include the information that will support my shortcomings, and at the same time, I need to make sure I don’t bother wasting my time taking notes on stuff that I can just improvise.

That Plot is Thicc!

The first thing I did was to map out everything that had already taken place. The campaign was originally a shared effort with multiple Dungeon Masters taking turns, but it eventually settled down to just me. My problem was that I used a purchased adventure, The Five Temples of the Earthmother, as a starting point. If you read the post about that adventure, you might recall that it was meant to be followed by additional material that was never delivered. Left to my own devices to fill in the blanks, I created an overly complicated backstory with multiple villains and plot lines.

My first order of business in our restart was to simplify everything down into something that still made narrative sense, but left plenty of room for the players to contribute and build the ongoing story. I set up a plot web and then made notes about each node and indicated the page in my notebook where I could find them. When the time came to finally sit down and play, I felt ready for anything.

The Best Laid Plans of Dice and Men

Everything went perfectly, for about 15 minutes. Then my players made a choice that I didn’t anticipate. They chose not to visit The Sinking Tower to discover the fate of our monk’s lost master, but instead decided to leave their companion behind (Patrick couldn’t make it that night and his character was missing) and continue to look for the final temple.

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It never occurred to me that they would choose to not pursue a particular sub-quest they had been following for so long when the answer was so close. It was totally my own fault. I made the mistake of adding in a deadline to complete the overall quest of the five temples in my initial encounter that was really just meant to provide exposition and a recap of events.

I’m embarrassed to admit that I reacted by railroading them back to where I wanted them to be, rather than just going ahead with what they wanted. In the end, they still decided not to explore the fate of the old monk. Afterwards, I thought about what aspect of my preparation was lacking. I had made an assumption about how they would choose, instead of just offering interesting choices. My new plot web features encounters and locations with possible connections and relationships that make narrative sense, but I’m not going to assume anything.


I’m looking forward to playing some board games this weekend. I hope that you get to play something fun with people you love, or even with people you just like. Roll dice. Move small bits of wood or cardboard tiles. Laugh. Eat snacks. Have fun.

1 thought on “Session Planning in Role Playing Games”

  1. Back when I DM’ed, long ago, I remember always trying to think of all the possibilities and plan for them, not wanting to be caught off guard and ruin the adventure for everyone. Ironically, I think my best session was one where some friends came over and said, “Let’s play D&D,” and I had nothing prepared, so I winged it. This is not something I’d want to do often. Or maybe even twice. But that one time it all fell into place and I really felt connected as a game-moderator-story-enabler.

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