Planning a Dnd Session

These first few paragraphs are just my own personal experience. If you want to understand how I plan sessions, skip down to Planning the Session.

Planning Dnd sessions used to be something I would do constantly. I was in high school, with no job, and easy classes so most of my time would be spent preparing for my weekly Dnd game. I would slavishly spend hours upon hours working on the same session, fine-tuning it to the point of ridiculousness. I would have elaborate plans for what my players would do as they would go about the session, and each step of the plan would lead to bigger and more complicated results that would end in a climactic finale!

Instead, what would happen is I would then start the session and within 5 minutes of letting the players loose, they would choose the “wrong” choice and completely derail all of the planning I had up to that point, and I would have to scramble to come up with some semblance of a story. After having my plans torn to shreds over and over again, I changed my philosophy on how I designed sessions and took the opposite extreme. Zero planning at all.

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Initially, this worked really well. If someone asked me to DM a game and gave me 5 minutes to prepare for it I was able to create something serviceable and entertaining. Sometimes, a lot of things wouldn’t make a lot of sense, but we didn’t care we were in a world where firebreathing lizards took to the skies and kidnapped princesses. For the past 2 years, I have stuck with this style, and it isn’t until I started playing in a brand new homebrew world that I began to notice chinks in its armor.

One of the reasons I was able to so successfully pull off the improv style in the past was because I was doing it in a setting I was intimately familiar with, my homebrew world of Arla. Creating NPC’s and plot threads was a breeze because I knew the world so well. If I created a certain mannerism, or if they had a specific accent that I came up with while playing I could easily say that they are from Tinder city and immediately know a ton about them and what they believed.

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When I tried to do it in a world I wasn’t as familiar with, I no longer had that ease of creating that I was so used to having in my main world. Characters turned from interesting and complex with a quick and easy backstory, to simply being caricatures of common fantasy tropes. For the past few months, I have been struggling with figuring out why that campaign felt hollow to me, and the answer lied in me not preparing sufficiently for my sessions.

Moving into 2019, I began to prepare for my first session of the year and I decided to stream it. Here is the YouTube link for those who are interested in watching. (Gollicking members are not allowed to watch!) Why this is interesting is because, for the first time in over 2 years, I was sitting down to actually prepare one of my sessions instead of just trusting that I can improv my way through it. And I discovered that planning sessions is actually incredibly fun, and is something I should absolutely be doing! I also learned that the way I have planned sessions in the past has been incredibly flawed and that to become a better DM I don’t need to forgo planning entirely, but instead be smarter about how I use my time spent planning.

Planning the Session

With all of that out of the way, we can now start talking about the meat and potatoes, planning the session. First things first, I think that in order to understand and prepare your session, it helps to understand what happened in the last session. If you take notes or have someone in the party take notes, it can really help you to tie the sessions together in the future. I know that I am horrifically bad at remembering what happened in the session that happened just a week ago, trying to call back to a session from a year ago is almost impossible. Something as simple as bullet points, or even just a single sentence summing up the session is good enough to help you jog your memory.

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Once you have begun to understand your past, the next step is to figure out what you want from the session. Do you want to have a battle on top of a train? Are you interested in featuring an Aboleth? Will they meet the resistance group of the city? Write this stuff down as things you want to happen during the session. Write it in as story beats that you are interested in having. It’s not vital how the players get to it, all you have to know is that you want your players to experience it. The circumstances leading up to it are volatile and shouldn’t be planned for, but the actual event is something you can prepare for. You have to be wary that you are worldbuilding instead of plotbuilding. Worldbuilding leads to a great sandbox for the players to explore. Plotbuilding straps the players to some rails and requires them to explore the world exactly how you envisioned it. If you want to read more about this aspect of planning, I write more about it here.

The last thing I do when I start preparing for my sessions is to simply worldbuild. As much as I love envisioning what the players might do when they get into my world, the truth of the matter is I can’t plan 5 steps ahead of them. Instead, I spend my time creating a world that feels real and can handle the players traveling to their heart’s content. DMing is largely improv, and preparing for the improv is an important step of the process.


Preparing for my sessions is something that I will constantly be improving upon. Going from overplanning to no planning, to somewhere in the middle is quite the change but it has taught me a lot about planning and what is good to plan for, and what is unnecessary. When preparing your sessions there is a simple 3 step process that I like to follow. First, you need to understand your previous sessions and remember what is important about them. Second, write down what you want to experience in the next session and put it down as a bullet point that you would like to explore. Finally, spend the rest of your time worldbuilding as this is the best way to prepare to improv, as this is how you can connect all of the bullet points together. Thank you all for reading, I hope you have a great week and an amazing Tuesday!

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