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The Hard Parts of DMing D&D

by Mike on 7 December 2021

Running D&D games isn't easy. It's one of the reasons blogs like SlyFlourish.com exist. There are a lot of tips, tricks, and levers we can use to make running this game easier.

Many DMs found themselves running D&D games because no one else would. Others aren't invested enough to go through the trouble of finding players, scheduling games, and all the rest — so we do it.

For new DMs, it can be worth knowing what we're getting into; identifying what the hard parts of DMing is and what we might do to ease some of that difficulty.

A while back Alyssa Visscher hosted a wonderful thread on Twitter asking for the hardest parts of DMing. The thread resulted in over 400 replies. With Alyssa's blessing, I harvested the replies and did a bit of text-mining to find common trends. Though far from perfect science, I came to the following common difficulties:

Finding players
Scheduling games
Fear of failure
Planning a session, campaign, or world
Preparing to improvise
Managing personalities
Being creative
Roleplaying NPCs

Many of these are hard problems to solve but there are some things to make them a little easier. In the rest of this essay I'll offer some tips and link to some larger discussions on these topics.

Hopefully, armed with these ideas, DMing D&D can be a little bit easier.

Finding Players

Finding the right players to join our table is the first hurdle when running a D&D game. We might recruit friends, co-workers, or members of our family. While an ideal D&D game has four to six players; the game can be quite enjoyable with just one player and one DM.

Not every player is a good fit for every table. Thus, it's worth our time to interview potential players to find those that fit the type of game we want to run.

Scheduling Games

A thousand memes talk about the difficulty of scheduling games. We're all busy. We all have other lives. Scheduling three or four hours a week is tough. There's no perfect model but the six plus two model might help. Try to find six players who can play regularly and two players who act as "on-call" players — those that can join in every so often to fill in a seat when others can't make it. Run the game with as few as four meaning that five people have to cancel before we can't run a game. If a regular player can't make it, we play anyway. Their character just fades into the background and fades back in the next time they can join up.

Running at Consistent Times

Try to run games every week at the same time. This helps players fit it into their regular weekly schedule and the commitments they have with the others in their lives.

Send a reminder email to your players each week to remind them about the game and give them the opportunity to let you know if they can't make it.

The Fear of Creative Failure

Likely the next biggest obstacle for DMing is getting past the fear of creating things in front of our friends. Anytime we're making art, and I definitely consider running a D&D game making art, fear hits us hard. This far tries to prevent us from doing any sort of creative activity, whether it's writing a book or running a D&D game for our friends.

I talk about this idea in my article on Battling the Resistance That Wants You to Fail at D&D.

We have to recognize this fear for what it is, a lizard-brain survival instinct keeping us from the hard parts of creativity. We all feel it. We all have to deal with it. Thank it for its service, set it aside, and go run a game for our friends.

Planning a Session

So we've got players coming to the game and we've gotten past the voice pushing us to avoid running our game. Now what do we actually run?

Planning for a session can be very daunting. There's no fixed instruction manual for it. Some DMs dive into the deep end, worrying about entire worlds and a long-term plot that can fill six novels.

Set all that aside. Focus on your next game. You don't need a whole campaign. You only need enough material to fill out your next session and plant the seeds for the session after that. Don't worry about the whole world. Think two horizons out.

Keep things simple. Build for the minimum viable D&D game. Try using the eight steps from Return of the Lazy Dungeon Master to frame your prep. Throw away the steps you don't need.

Preparing to Improvise

It's hard not to build out your game as much as possible to remove any uncertainty from the situation. We want our friends to have fun. We want to feel prepared. So we plan and plan and plan. But the best parts of the game are the parts we dont plan for. Not only can we run a D&D game with less prepared than we think — often that game can be more fun.

This means doing a few things.

First, prepare to improvise. Find the tools and tricks that help you move the game in the direction it heads at the table. Here are some examples of tools, both for in-person and online play, that can help you improvise:

A good dry-erase or wet erase battle map for in-person play (check out the Pathfinder Flip Mat).
An easy-to-use virtual tabletop where you can quickly show positioning (check out Owlbear Rodeo)
Blank index cards or a scratch pad (like Notion) for taking and sharing notes.
Lots of maps you can choose from. I love Dyson Logos for maps.
Good generic monster tokens or virtual tokens built with Token Stamp or the universal tokens in Owlbear Rodeo.
A good list of random names.
A good cheat sheet so you can quickly look up common mechanics.

Here's an article on the Lazy DM's Toolkit describing lots of tools built to help you improvise during the game.

And here's a video on Seven Fantastic Tools to Run D&D Online also intended to help you prepare to improvise.

Managing Personalities

Unfortunately, where there's people, there are personality conflicts. Also unfortunately, and unfairly, it often falls to us DMs to manage those conflicts. Working with people is a lifelong valuable goal, and is beyond the scope of this article, but when we think about who we bring to our game and how we ensure our games go smoothly, we do have a few tricks.

First, run a session zero. Session zeroes help you set your baseline expectations for the game and tell the players what's allowed in the game and what is not. It helps steer the game in the right direction before the game begins. This can cover a lot of potential personality clashes right away. Saying something like "no stealing from other characters and no non-consensual violence between characters" covers a lot of common problems. "No working on your own, work with the group" covers many of the "it's what my character would do" sorts of problems. Set those baselines right away and you can hit a lot of common problems before they ever come up.

Second, use safety tools. Safety tools don't have to just be for really horrible situations; they can be used just to get a game on track. I'm a huge fan of pause for a minute to give everyone a way to pause the game, pop out of character, and address issues out of the game so things happen smoothly in the game. Use it and feel free to use it often.

These don't solve all personality issues that can come up but it can help get things started on the right track and stay heading in the right direction.

Being Creative

Where do we get our ideas? Neil Gaimen once quipped "From a little ideas shop in Bognor Regis". The real answer is "everywhere". How do we be creative? How do we get creative? Stephen King says "If you want to be a writer, you must do two things above all others: read a lot and write a lot."

For us, that means absorbing a lot of fiction and running a lot of games. There are lots of ways to fuel our creative furnace:

Play good video games
Watch good movies
Watch good TV shows
Read good books
Listen to good audiobooks
Read good RPG books

Suck in ideas from everywhere. Absorb good fiction from whatever form it comes. Think about how you might use parts of it in your game — NPCs, locations, fantastic monuments, cool situations.

Be wary, however, of trying to use plots from fiction as plots for your roleplaying games. Most of the time they don't work.

Here are some good quest ideas from movies like Seven Samurai but there are also some bad ones.

Instead of taking stories from fiction, take other discreet ideas like NPCs, locations, monuments, and situations. Take small ideas.

Roleplaying NPCs

How to roleplay NPCs is a common hurtle for newer dungeon masters. Luckily, it's only as hard as we want it to be. If you worry that roleplaying an NPC is going to be like bad grammar-school theater, you can describe how an NPC acts or interacts in the third person:

"The innkeeper greets you warmly and offers you some fine stew and bread before mentioning that, as adventures, he could surely use your help".

Or, even better, don't give a shit. Ham it up. These are your friends. You don't have to be perfect. You don't have to be great at it. Just drop yourself into the character and enjoy their shoes.

One good way to get better at voices is to listen to how audiobook narrators do it. Listen to how they voice their characters. Practice it. And listen to some great fiction at the same time. Audiobooks are great.

Keep It Simple

These aren't the only rough bumps you might roll over while trying to set up a D&D game, but they cover the most common ones DMs share over the years. Most importantly is to not let "the resistance" push you away from it. Get past it. Call some friends, even one friend, and plan a nice, short, and simple D&D game. Keep things simple. Keep things focused. Cut things down to the minimum you need to enjoy a great game of D&D.

Play a D&D game. Then play another.