Roll for Initiative

Goblins, orcs, and ogres… while I’m not so jaded as a high school principal to suggest that this is the clientele that fills our school hallways, I’m dorky enough to make the pitch that if I can handle a hoard of kobolds or bugbears, I can handle a hoard of teenagers. (A variation on that “classic” maxim, I suppose: “If you can dodge a wrench, you can dodge a ball.”) Hear me out.

This summer I had the opportunity to step in on a panel for a friend who was teaching a college class for aspiring administrators. It was a lot of fun and I was humbled by the depth of wisdom from the others on the panel. They were so thoughtful about such a range of topics, and I thought to myself: the lessons we learn and can pass on really can make a difference.

And while I have had my own fair share of formative experiences as a principal (and before that as an assistant principal) I’m also inspired by sources decidedly not academic. I’ve written before about how poetry, Star Wars, Star Trek, and even nautical fiction have inspired my work as a principal, and last spring I added another nontraditional source to that list: Dungeons & Dragons.

I posted about DMing for my kids not long after the pandemic started, and while I was far from a polished Dungeon Master (far, far, far from it), the experience was really fun and left me with a taste to do it again.

Now I’m a reader and the kind of person who likes to learn, so ahead of jumping back into the Dungeon Master’s chair I picked up a couple of books and took to YouTube to see what I could do better. It was a delightful exercise in seeing a whole new world I didn’t know anything about (my only other experience with D&D was playing a handful of games when I was in middle school back in the early ‘80s). My favorite surprise find, hands down, was Web DM.

With lots of wit, laughter, and easy Texas charm, Jonathan Pruitt and Jim Davis cover just about everything a fellow like me, who came late to D&D, needs to know. For anyone who hasn’t seen Web DM, it’s just two fellows sitting at a table surrounded by dice, miniatures, and the trappings of epic fantasy roleplaying. They introduce a topic, provide specific examples, and banter back and forth for about half an hour. I love that they’re engaging and knowledgeable, but also never judgemental about different ways of doing things. They have opinions, sure, but they’re not mean and always leave room for other points of view. They invite viewers to think, and one episode in particular had me thinking about the similarities between being a principal and being a DM.

The episode Problem DMs: Overcoming Game Master Issues in 5e Dungeons & Dragons pretty much sums up a good swath of the kinds of principals I’ve met in my quarter century in education. If I were putting together a college class for aspiring administrators this would be a required text.

Because as nutty as it might seem, Web DM’s description of different kinds of Dungeon Masters could serve as a great reminder of some of the important things about leading a school and a cautionary tale to anyone reflecting on his or her own practice as a school administrator.

The episode starts with a meaningful reminder: “The Dungeon Master is another player at the table. They have different tools, they have different pieces that they use, but … they’re not like this special figure…” So too, I would offer, the principal is one of a staff of adults working together to help kids, and as Jim Davis says of a DM, “they need to be empowered to make decisions, they need to be empowered to make rulings, the rules need to support the Dungeon Master in running the game, but it’s not like we’re sitting down to be ruled by the iron fist of tyranny.”

“What we’re talking about today,” Davis explains, “is really Dungeon Master styles, and a mismatch between Dungeon Master styles and player styles that create problems.” As they describe it, the different styles aren’t bad in and of themselves, but can seem so if mismatched with the players at the table. It’s not unlike a school, where it works best when the culture of a site and the personality of a principal are really in sync. To help this happen, principals, like DMs, should know their type.

And what are those types of Dungeon Masters? Well…

The Optimiser, always challenging those around him, planning, preparing, and showing no mercy. The result of this style, Jim Davis explains, can be a “well oiled machine” …by necessity. This competitive environment works for those who want a high pressure experience and the sense of accomplishment that comes from “winning” a difficult battle. Optimization, however, comes at a price. You can see this in schools, where it’s easy to understand that sometimes the motivation for “optimizing” comes externally, but the results can be as unsustainable as they would be when the players and DM don’t all agree that this style is the way they want to be playing.

Adversarial DMing is a way of describing a Dungeon Master who is interested in having power and control. While this might work for the DM, it can lead to players feeling animosity, fear, and maybe that they shouldn’t continue. Davis suggests that sometimes players second guess themselves when they’re in situations with adversarial DMs and wonder if they’re not having fun or succeeding because of “something I did.” Does this happen on a school staff? If you don’t know the answer, site administrators, go ask your staff.

The Rules as Written DM scolds players for not knowing the ins and outs of the Player’s Handbook, looks up every rule, or hesitates to make a decision on the fly in fear of doing something wrong. “Unless you have a table full of rule lawyers” Davis tells the audience, this style of play can be difficult. As in D&D, rules, protocols, and expectations help provide an armature on which education can be fashioned into a viable sculpture, and like D&D when those rules are placed above the humanity of the enterprise the results can be frustrating, disheartening, and lead to lamentable results.

Jim Davis makes the point, however, that Adversarial DMs and Rules as Written DMs should be seen as existing as a “matter of degree.” Sometimes, he explains, it’s appropriate to say honestly: “My f***ing dragon is trying to kill you. I hope he doesn’t. I like your characters.” (A note here: Web DM is peppered with occasional F-bombs; truth be told, behind closed doors, so too is school administration.) Rules aren’t bad, and a lack of structure can be. The dance that DMs and principals must master, or continue to attempt to master, is balancing between the two.

My Precious House Rules DM is the person who “hands over a 37 page living document” describing how things are done at this particular gaming table. Not unlike some schools, where specific traditions, agreed upon culture, and unique ways of doing business are a part of what makes things work, “homebrew” D&D, if agreed on by the party, can lead to special and marvelous results. As Davis says of such gaming groups, “more power to them, they are playing the game in a time honored way.” …if everyone agrees. Homebrew for a player who is a traditional rule follower, however, might not be the right fit.

That made me think of a friend of mine who is an AP History teacher at a high octane academic school in Southern California. His students routinely excel on the AP exams and he loves the pressure and rewards of working in a system that demands much and expects results. He delivers them, and he told me once that he couldn’t imagine teaching at my school (where tie-dye could be the official school color). It just wouldn’t be a good fit, he explained. As much as I respect him as a teacher, and that is a lot, I think he’s right. He’s comfortable with the educational version of an Optimizer DM and would feel out of step with my decidedly homebrew world. 

But even house rules happen on a continuum. 

Hater DMs, subscribe to the “not in my game” aesthetic. Davis gives an example from a game when he DMed in this way …for a specific purpose, but as Pruitt interjects: “maybe it’s okay to have personal preference, but you don’t have to impose it on someone else.” Good advice beyond D&D. For me that’s spelling bees

“There is a point,” Jim Davis says, “between too permissive and too restrictive that works for your gaming group. And that means that there is a compromise between everyone who is at that table, not just what one person wants and then everyone else has to deal with it.”

The Quiet DM v. The TMI DM. Davis and Pruitt use the example of under and over description to describe these two kinds of Dungeon Masters, admitting times they’ve each fallen into these behaviors. Describing the DM as “the players’ eyes and ears” and explaining the importance of fulfilling this role, they discuss how easy it is to struggle with the discrepancy between what the DM knows and understands (Dungeon Masters have the whole picture of the adventure) and the players know (who are experiencing the adventure a step at a time) and the challenge of the “slow releasing of information that takes place between the interaction of the game.” Quiet, TMI …as a principal, I have been both. Maybe both this week.

“One last thing,” Davis adds toward the end of the video that is as applicable to the gaming table as it is to the schoolhouse as it is to any environment in which we find ourselves, “if you have a DM who does not respect your boundaries that is a huge f***ing red flag. If they do not respect your boundaries when you are playing together, then they are not going to respect your boundaries outside of the play, they are not going to respect your boundaries in any other aspect.” This step back from listing styles of DMing and addressing the fundamental issue of respect and humanity is a reminder that the world we live in is fraught with opportunities both good and bad. His advice on gaming applies to more than the gaming table, and it resonated with me as a part of a staff when he said: “You want to play with people who you trust and you want to play with people who are going to treat you with respect.”

Pruitt brings the conversation to a close with a couple of questions that (if this connection between being a Dungeon Master and a principal is to be believed) would be the cornerstone to a meaningful discussion in that fictitious college class for aspiring administrators: “How do you not do all the things that we’ve talked about?” and “What are some ways to better align DM and player expectations?”

Because it’s that alignment of everyone in the group, gaming group or group of educators, that is at the heart of a successful, fun, and productive experience.

The last few minutes of the episode, addressing the importance of communication, honesty, and “knowing yourself” are heartfelt and wise. So too is the advice about asking for feedback, adjusting to those responses, and how to set clear expectations early in the process. “If you care about [your players] as human beings,” Davis says, “then you can avoid a lot of these problem behaviors.” 

Caring about others as people. What would happen if every educator started from here?

“Be kind,” he concludes, “and be respectful, and a lot of these problems will go away. Not all of them, so it’s good to know what you can do.”

The whole show is a fantastic 37 minutes of wisdom for DMs and principals, maybe not honestly something that will make it on a college syllabus, but more insightful than some scholarly articles that will.

…a side note, and if anyone is still reading this (thank you) then maybe you’ll indulge me a paragraph or three that I’d include if sharing this with RPG minded aspiring administrators… (What does the Venn diagram of D&D fans and school administrators look like?) Another episode of Web DM that resonated with me as a principal took on the important topic of sexism, as real in the world of high school administration as it is in Dungeons & Dragons. 

With Web DM co-founder Emma Lambert sitting between them, the regular hosts asked questions and listened as she broke down a reality that answered the episode’s premise “Let’s Talk About Stereotypes of Women in 5e D&D.”

I’ve known and worked with some amazing women in high school administration, but the reality on the ground is that when I look around at a meeting of principals my status as a white male has put me in the majority in every district where I have worked. So too, it seems, much D&D.

In 17 minutes or so, she holds up and knocks down stereotypes. Looking at her fellow Web DMers, for instance, she speaks truth while poking fun with lines like: “A munchkin stereotype or even a neckbeard stereotype… in some ways their problem is that they care about the game too much.” The fellows nod. “That’s not necessarily seen as an option for women.”

They make the point that from its earliest editions D&D has had inclusive language, but that has not always been the practice at the table (or, perhaps the schoolhouse). 

There were more parallels, from assumptions of motivation to how different genders are discussed in the system. “There has always been a very inclusive side to this culture,” Lambert explains, “and there’s always been a very exclusive side, and you’re always going to run into it.”

D&D, she means, not education, but…

The world of school administration can learn from lots of sources inside education and beyond. Web DM has made me a more thoughtful principal. And someday, who knows, maybe I’ll get to DM for a group of educators. Wouldn’t that be amazing. No promises that it would be as inspiring as that panel I got to serve on, and even after watching my share of Pruitt and Jim Davis I’m certainly no polished DM, but it sure could be fun.

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