Prepare to Improvise

Over a year ago I worked on this series that I called the “Learn From My Mistakes Series”. It was a decently popular series that I wrote on /r/DndBehindTheScreen. However as I look back at it now, there are a lot of things that could have been improved upon in that series. So for the next couple of weeks I will be working on revamping my original articles, and adding a few more articles to the original series. If you are interested to see the original articles and the discussion around them, you can find them here.

Preparing for your Sessions

When I first began to DM I had a lot of free time. As a direct result of this I would spend hours upon hours preparing for each session of Dnd. For every hour of play I had probably spent 4 hours or more on prep. This was overkill, but theoretically the more time you spent preparing for your sessions the better the session would become. This did not prove to be the case, and my sessions ended up turning out very mediocre despite the amount of preparation I would put into my sessions. 
Fast forward to today and I am no longer preparing for my sessions whatsoever. I begin my sessions with no idea of what my players are going to do, and because of this I have had some of the most fun sessions I have ever played. My players feel like they can do anything, and I feel sufficently ready to react to whatever my players do. Despite the lack of preparation I feel more prepared than ever before, and my sessions have improved dramatically. 
How could not preparing at all make my sessions better than if I had prepared for them? DM experience can be counted as one thing, but I know that my sessions are better as a result of me not preparing directly for them. I am instead preparing to improvise, and this allows me to be much more flexible with my campaign and players. I am no longer planning ahead for what my players are going to do, and instead trying to react to what my players are going to do. In my old campaign I would plan ahead as to how my players would react in any given situation, and I would plan my session accordingly. If things didn’t go the way I had planned I would change the environment to get the players down my preset path. In other words, I was railroading my players to accomadate my plans.

The Dangers of Railroading

Railroading can be something that can be difficult to recognize. Railroading is like a defense mechanism. When your players begin to do things that you haven’t planned for, the natural reaction is to try and get things back into your order and control. One of the greatest things I have learned as a DM is that oftentimes railroading will happen because of our preparation, and the way we plan ahead for our next session. In our attempt to be ready for the next game, we often plan out ahead what will happen. When things don’t go our envisioned way, we do our best to put things back in place, and this inevitably leads to railroading. Our prior expectations of how the game should be played out changes how we play the game, and how our players get to play the game.
However railroading can be easily avoided and I believe that it starts with how we prepare our games in the first place. I personally no longer prepare for my games at all, and I can do this due to my prior experience. This is one of the best methods in removing railroading from your games, because you no longer have any prior expectations as to how the session will play out. My sessions are more fluid and free form as a result of this, and I have decided to instead react to my players antics, instead of planning proactively around them. This gives my players, and me a lot more agency in how we play the game, and I consider agency to be one of the most important elements concerning Dnd. 
However, playing a game without any preparation can be a difficult task and is not recommended to everyone. Oftentimes not preparing for a game can be a very difficult, and even a detrimental thing to do. Preparation for a game can be a very good thing, however in order to avoid railroading it must be done in a way that discourages railroading. And the best way to do this is to prepare to improvise. By preparing to improvise you are ready to react to whatever the players do, and you will have a more enjoyable game as a result. 

Prepare to Improvise

A mistake many DM’s make when it comes to preparing their next session is that they will plan out the series of events that will happen in their next session. This can be a very detrimental way to plan out your sessions as it does not leave you room to improvise if your players go off course. If you ever find yourself saying “when the players do . . . ” that typically means you are planning out a series of events that is very likely to not even occur. This can lead to railroading, and can ruin the fun for your players. What I instead like to do, when I prepare my sessions is that I plan to improvise. I go off the assumption that my players will do whatever the hell they want, and I will have to react to my players antics. It’s the difference between proactive and reactive preparation that can make for a good session or not. Proactive preparation can be a good thing, if it is used correctly, but planning out the actions of the players is not a good thing to do. 
When I prepare to improvise I don’t waste time with what the story will look like. One of the key things about Dnd is that it is a cooperative story telling game, and if I lay down the story tracks before hand I might as well write a book. Flexible preparation is key when it comes to preparation, as the amount of choices your players have available to them are impossible and impracticable to plan for. By preparing with broad strokes you allow yourself a lot more freedom in the improvisation department, which I believe is one of the main components of DMing. 
One of the simplest and most effective ways to plan to improvise is to create random roll tables. I like to take some time occasionally to write down a few things about what kind of encounters my players will run into in certain parts of my world. For example, in the Oaklean Forest I might make a table listing all of the potential monsters they might run into while there, while I might make a table for the potential NPC’s they may run into in the city of Theed. Random roll tables have almost endless possibilities, and are a great point to improvise off of. Keep the details in your random roll tables low, and you give yourself room to improvise for whatever circumstances your players might be in.
Another method I like to use is simply re-purposing my prep. Let’s say that I plan a dungeon called the Crypt of Agadeem, that is filled to the brim with undead minions. I am hoping for my players to go to that dungeon, but they instead decide to travel to the Maroon Mountain. Instead of forcing my players to go to the Crypt of Agadeem, I instead re-purpose the dungeon by changing the flavor of it. Instead of zombies I’ll have dwarves guarding the entrance. Instead of a mastermind Lich controlling all of the zombies, it can be a Mindflayer forcing all of the dwarves to obey his will. Changing the flavor of a dungeon allows you to effectively use your prep, without forcing you to railroad your players. And if you decide that you don’t need to do this, you still have the dungeon on hand for when your players do decide to visit the Crypt of Agadeem.
However one of the main, and most effective ways I prepare to improvise is to simply build my world. Worldbuilding is a very fun hobby for me, and I like to spend a lot of time working on my world. But the great thing about worldbuilding is that it allows me to prepare to improvise because I become very familiar with the setting. If my players decide to head south, I know that they are heading towards the capital city of Silver Mesa and can tell them how the environment and people change. By becoming familiar with my setting, I can give my players a greater degree of freedom, and be prepared for wherever they go. 
Preparing to improvise may seem counterintutive but by doing this you give yourself and your players more freedom at the table. Dnd is a game about open ended possibilities, and by preparing in this fashion your players are now free to do whatever they want. It no longer is a game about the players fighting the DM to get what they want, and instead is a game about the players doing what they want. 


Railroading can be a very easy trap to fall into, and I am sure any DM worth his salt has done it his/her fair share of times. One of the clearest and simplest ways to avoid it is to simply prepare for the right things. By preparing to improvise, you allow yourself and your players a greater sense of freedom that can open up your games in ways that you could never imagine. If you are feeling up to the challenge try to play a session of Dnd with absolutely no prep put into it beforehand. It can be a difficult challenge at first, but doing so can teach you many things about DMing that you may not have learned otherwise. 
Thank you for reading this weeks installment! Next weeks post will go into detail on how to create and maintain a stable and healthy Dnd group. Players can be fickle creatures, and it is important that you choose the correct players for the type of game you want to play. Have a great week, and an amazing Tuesday!

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