Real World Problems, Fantastical Solutions - Critical Thinking through D&D

Real World Problems, Fantastical Solutions - Critical Thinking through D&D

Last year, I had a party of students, some more experienced than others, but none had been playing much more than a year. They came across a large mound of boulders stacked 60 feet high and they had been given instructions that there was a treasure trove at the top of the mound. When asked what they were going to do next, they shrugged and said, “Let’s climb the mound”. I asked them to roll an Athletics check and the dragonborn wizard failed, fell down and sustained damage. Already hurt from the fight that had just happened, and of low level, the wizard was looking pretty hurt. At this point, the party had reached halfway up the mound. I asked them what they were going to do. They said they would wait for the wizard to catch up. The wizard got up, dusted himself off, and held his breath as he made the Athletics check. He made a sigh of relief as he managed to make a successful roll. 

“What now?”, I said with a neutral and blank face, all the while slightly frustrated and a little amused at their lack of forethought. I knew where this was going. They said they would climb the rest of the way. Unsurprisingly, with the significant negative modifier on his Strength, the wizard failed his next roll. He also failed the Dexterity check to catch himself halfway down…. And so we had a situation of the party most of the way up the 60 foot mound, and their wizard friend at the bottom of the mound bleeding out and making death saving throws… The elven ranger came to the rescue and even had the presence of mind to wedge his 50 foot rope between the boulders before repelling down with a healing potion in hand.

After the session, I asked my students to look at their inventories. I then asked them how they could have better climbed the mound. 

“Ropes!... Oh, grappling hooks!” a couple of them said. Eventually, after eyeing them over a pregnant pause: “...we probably should have sent one person up first.” 

The amazing thing to me was that these were amongst some of the brightest students in the school. Certainly, I know that I had at least three of the top mathematicians from three different year groups, and also one of the top debaters/public speakers in his year. This perplexed me: Why is that they couldn’t think logically and strategically in this situation?

Perhaps part of it was because they were still thinking of this as an abstract exercise. If they were presented with a real mound of boulders, with real backpacks, real ropes and grappling hooks, and a real climb, they might have sent up their best climber first, and made good use of the ropes and grappling hooks. I think perhaps because of the open nature of D&D, where rope and grappling hooks are just part of a standard pack and they hadn’t used them before, they thought those items were just part of the furniture. They also hadn’t had to work hard to gain them or even bought them. Not too long ago, there were video games where, if you gained a piece of equipment, you knew you had to use it somewhere, so you were always on the lookout for a situation to use it.

SOURCE:  Walmart

SOURCE: Walmart


These students were also experienced game players as well, so why didn’t their video game experience help them with this situation? Surely computer games tested their ingenuity?


In a computer game, the game would probably have highlighted a way to use the rope and grappling hook, probably with a specific button to press or tutorial and then made a feature of them, or given specific cues to use them. I have also realised what usually happens with a difficult task for most computer gamers (apologies to those who don’t do this): 

1. You come across a difficult task. 

2. You might make one or two attempts at it, maybe even three or four if you’re persistent.

3. You go and look up the solution on the internet. 

I know because I do exactly the same, and I usually love solving problems. The problem with computer games is that there can sometimes be just one solution, and that solution isn’t always obvious. Creativity and innovation aren’t really rewarded in computer games, but a good DM usually will. Also, even if there is more than one solution, there may be an optimal solution and that can go a ways to “winning the game.” “Winning the game” just isn’t part of the mentality in D&D, unless you count staying alive and becoming more experienced, but that’s a discussion for another time.

At the end of the day, I think moving from the abstract to the applied and problem solving in unfamiliar situations, especially when there isn’t a single “best” answer would definitely be classified as “Critical Thinking” skills.   

SOURCE:  eschoolnews

SOURCE: eschoolnews

Critical thinking is one of those buzzwords in education; one that I suspect many cannot properly define (it’s interesting to note that even Wikipedia says that “the subject is complex, and several different definitions exist”). To me, critical thinking is the ability to solve problems (mostly real world ones) that haven’t been prepared for, perhaps something you have never seen before; in effect, thinking on your feet. If you look at the list of qualities that employers are looking for in graduates, or the lists of skills that employers want schools to teach, or lists of things that school should teach but don’t, critical thinking will probably be in there somewhere.

So how, in the rarefied atmosphere of academia, do we train good critical thinkers?

In some regards, we can’t prepare students for every situation, and in some ways we can only simulate what students might experience in the real world and you will never know how a student will react to an unfamiliar problem or situation until they face it, especially in a crisis or under pressure.

SOURCE:  stickpng

SOURCE: stickpng

On the other hand, we can make students more familiar with the idea of thinking for themselves, to become more comfortable with dealing with the unfamiliar and not to panic if they come across something they have never seen before.

As a mathematics teacher, I often throw unfamiliar questions on the board at the start of my lesson and ask the students to solve them without discussing them. I encourage the students to try the problems and just to “have a go” rather than freezing and putting down nothing at all. A mantra I often use is: “If you write nothing, what do you get?” “Nothing!”, my students reply. 

Since I don’t take in the marks for these questions, I encourage them to explore and try things. This hopefully takes out the fear of getting things wrong. 

Whilst some of the questions are consolidation of things we have been working on, or even reminders of previous topics and revision from previous years, I occasionally put up a question that they will have never seen before and ask them to see if they can figure it out. For example, this is where I might introduce a simultaneous equations problem with no solutions (graphically, two parallel lines). This should leave them scratching their heads, but with some thought, they should be able to vocalise some understanding of what went wrong with the question, or at least their traditional way of solving the question. This kind of situation teaches them a few things: 

Firstly, that it’s ok to try and fail. 

Secondly, they learn not to panic if they come across something unfamiliar. 

Thirdly, they can sometimes just work things out, and don’t need to have been formally taught a method to solve something. 

In my mind, these are very much critical thinking skills. 


So how do these translate into real world critical thinking skills? Well, students are far too ready to put on their different “hats”, and I know this from my own experience. A student is who is good at Mathematics, may not be good at English, or French, or Art. I was very good at Mathematics, so throwing an unfamiliar problem at me when I had my “Mathematics Hat” on would be fine. I was so confident in my ability in mathematics, I relished being given something harder and more interesting, partly simply because it was more interesting (a good way to teach maths is to try and get students to see the problems as little puzzles to figure out), and also partly because it gave me an opportunity to show off how good I was. When I had on my “French Hat,” I would freeze up. My confidence was tiny when it came to my ability with foreign languages. 

I asked some of my students about how critical thinkings skills are used in English. They suggested “unseen poems”, where they are given an unfamiliar text and have to figure out the meaning, metaphor and subtext within the poem. I was good at English, and so I still love to hear, and occasionally dabble in word play. As long as it wasn’t examined, this is something that I would have considered quite fun. 

SOURCE:  DM Magazine

SOURCE: DM Magazine

Having these “subject hats,” whilst having confidence in any subject and teaching critical thinking skills through that subject will be useful, makes the skills less transferable. I do believe that some of these walls do break down over the years, however, I still shy away from learning foreign languages and struggle when put in a situation where I might need to communicate with someone who doesn’t speak any English. I think this just shows some of the benefits, and damage, that a teacher can do to their students and how important it is that they build their confidence, even if they are weak in a particular subject. Again, a good reason why I take my job as a teacher so seriously, but that is a topic for another place and another forum.

D&D and other roleplaying games break those academic constraints. Embodying heroes, or at least extra-ordinary individuals, players throw themselves at difficult situations. An adventure would become very stale and boring if there wasn’t some test of their ingenuity and this is what most DMs crave. I am a member of a few DM groups on Facebook, and it is heartening, encouraging and inspiring to see the passion these fellow DMs have for creating new and interesting challenges. They are not just satisfied with the same Dungeon Hack. If they were, there are plenty of board games that can scratch those itches, with no need for Dungeon Master. Some like riddles, some do not. Some like puzzles, whilst others like devious traps. I love the creativity of these DMs and a lot of it is driven, not just by the DMs, but by the players themselves who seek out the difficult situations and relish in the challenges. And it’s not just intellectual challenges like riddles, puzzles and traps; it can be roleplaying challenges, or moral quandaries (GM Advice: 6 Moral Dilemmas for Your PCs). DMs in these groups ask, discuss, agonise and debate over things like how to encourage their players to be better roleplayers, problem solvers, less like murder hobos, less combat oriented, and more creative. They are passionate about putting their players into unfamiliar situations and even uncomfortable ones.

SOURCE:  Blogspot

SOURCE: Blogspot

A few years ago, I ran the Dark Legacy of Evard (4E) adventure with some students. There was a mix of experienced and inexperienced players, some had played for a few years. Despite this, perhaps partly because they had a large unwieldy group of eight, when given a choice of two options, they foolishly decided to split the party. Four of the party went to the Armory (pictured below) to get weapons and equipment for the local militia.

Whilst they dispatched the three Leeching Shadows (minions with 1 hp each) fairly easily. The two spider swarms proved to be much more difficult. They saw on top of the Armory a large Deathjump Spider. Rather than helping his friends finish off the spider swarms, the human rogue decided to climb the armory to attack the currently unmoving giant spider. The subsequent combat resulted in three of the party dying, and the other fleeing for his life as the giant deadly, but previous uninvolved spider joined the fight . In the post match analysis, the rogue admitted that it was foolish to engage with a creature, clearly visible but out of range from being involved, before finishing off the other creatures first. Whilst they did use the bridges to good effect as a bottleneck for the Leeching Shadows, they figured out afterwards that they may been able to use the canal as a place to retreat to, but also a place from which to launch attacks against spider swarms who would not have followed them there. I certainly have found DMing students that a “post-match analysis” is a great way of teaching them tactics and to make them more aware of the things they might do to improve in future.

In the real world, many interview processes involve asking their interviewees awkward questions or try to hypothetically put them into difficult situations to roleplay. Some may even use group work to see how they fare as part of the group: to see who are the leaders and whether as a group they can think clearly, logically and strategically, as well as whether they can communicate well when put into difficult situations. All of these skill, and especially “critical thinking skills” - thinking clearly, logically and strategically when put into unusual and difficult situations - are practiced and greatly improved by playing D&D. I think this is true, especially when coupled with a “post-encounter” analysis. For anyone DMing with young groups, I would high recommend an occasional debrief of this sort. It will greatly improve their thought process and tactical skills, give them an appreciation for how to approach the game logically and strategically, and add a lot of depth to their combat. So too, would I recommend that DMs think how they can plan combats and in fact, all other encounters and challenges so that the players can be strategic about their play. Encourage and reward creativity, and the joy the success will do the rest.

Moral of the story: encourage your players to stop and think and plan. 

For now, I’m just waiting for the day when an interviewer starts a question with: “So you and your party are guarding a caravan on a road well known for Orc attacks….”


As a mathematician, I am well aware of that my opinions and even observations are from a very small sample group. This is why this is a blog and an opinion piece. I would love to hear of your experiences and opinions. 

Many thanks, 

Sam, The Educational DM (Twitter @DMEducational )

Image Header: DnD Next Playtest - WotC

Getting into D&D

Getting into D&D