How Learning to Play Dungeons & Dragons Makes Me a Better Creative Leader

December 29, 2015


With the holiday season upon us, and lots of hours spent with friends and family sprawled around living rooms, assembling toys and reading/arguing over directions to gadgets and games I’m grateful for a very particular game I’ve been learning to play this year and its singular effect on my own creativity: Dungeons & Dragons.


That’s right – I’m in my mid-30s and learning to play DnD for the first time. This kind of statement is often met with derision or “L-shaped” hand-signals on people’s foreheads, though for the most part geek culture has moved into the mainstream these days.  Some folks will have memories of this imaginative role playing game, and the fantasy novel dynasty it also spurred, during the 1980s frenzy in some religious circles over accusations of devil worship and satanic possession supposedly inspired by the game. The only things I have been possessed by in the five months I’ve been playing are a sense of joy from the challenges my imagination has faced and the endless creativity of my fellow players and our brilliant Game Master (GM).

I am proud and excited to be a total novice, and when I say novice, I mean to the whole gaming/quest culture, not just DnD:  I stopped playing video games when they went 3-D; I don’t even play Candy Crush. I text in complete sentences. I only learned what Leet speak is because of a friend who was texting me in what felt like cell phone hieroglyphics. As an only child, I have absolutely no street cred in terms of understanding combat – my natural combat defense is to run to a corner, curl up in a ball, and shriek.

In fact, all four of us in the group are novices at DnD, though at least two have significant video gaming experience and the third has a multi-player board game history. But, as my GM pointed out, I have a theatre background, and working on new plays for most of my career has honed my narrative skills and enabled me to create a backstory for my character that influences how she operates in this DnD world – all creative, innovative acts, particularly when put to use in real time to solve problems or spur action in our campaign’s storyline.


Here, in short, is how the game works:  The version of Dungeons & Dragons that I am playing (a combo of 3.5 and Pathfinder for my fellow DnD-ers) is in essence a hybrid between a board game and a role-playing game.  Each player creates a character, and the merry company of characters are given a quest to pursue.  Our company consists of a Minotaur, a half-elf monk, a gnome (me) and a kender (like a hobbit but with no fear, more excitability and obliviousness, and very quick fingers when it comes to “acquiring” things from others).

When a character wants to take action on something – from fishing for information, to jumping over a pit, to firing an arrow accurately – a player rolls dice to determine the character’s success at that action. The game is officiated by the Game Master (GM) or Dungeon Master (DM), who is the master storyteller, rule keeper, and player of all other characters (evil and good) that the players encounter during their quest. A “campaign” can last months or even years of real time, with a player’s character getting stronger, more experienced…or killed off. The complexity of the world and its rules are codified in 300-plus page player handbooks and the scope of imagination on display in those books is quite stunning.

Beyond the fact that I enjoy the company of my fellow players, I always look forward to the ways in which I will be required to exercise my imagination, stretch my creative-problem solving skills, and how I can take the skills I’m honing during this play into my work and my role as a leader.


Playing DnD is like getting a creativity workout every couple of weeks. The more I do the workout, the more imaginative and creative I get at solving problems. This time to play inspired me to draw my character, though I rarely do visual art. It’s inspired me to cook a spiced potato dish that is referenced multiple times in the novels. It’s also drawn my attention to the many life skills I’m learning in the process of viewing the game both from my character’s viewpoint and my own, including:

Learn to work with your strengths and those of your team. I’d like to introduce you to Trig Conniption – the middle-aged Gnome rogue I created who has a major chip on her shoulder for being kicked out of her homeland because she was good at inventing things that actually work.  Trig is only three and half feet tall, which means she has limited capabilities in combat.  Once I’d received several sessions of instruction from our GM to learn how to best utilize my character, I’ve been able to help play to my character’s strengths and aid my companions.  I’ve also managed to die a whole lot less.  Lesson: Look at the strengths and weaknesses of your teams – strategize together or guide each other to help the entire group become more effective.

Sometimes, you just roll a 1. The most common die used in DnD is a 20-sided die.  Roll a 20 and you automatically succeed at whatever you’re trying to do (with a few exceptions).  Roll a 1 and you automatically fail.  In life, sometimes you just roll a 1 and whatever cool idea you had planned not only fails but often ends up causing some damage to you.  Deal with it and figure out what you’re going to try the next round.

roll 1

Go for the called-shot.  Called shots are often very specific maneuvers in combat that require hitting a smaller area of the body or trying to go for a specific object, and you incur all sorts of penalties that will lower your chances of succeeding.  But the one time you DO succeed you can have some game-changing success.

Delay your action. At the beginning of every combat sequence the company has to “roll for initiative” which determines, based on your die roll and your character’s inherent qualities, what order each player – and opposition characters – take in the combat.  My character’s initiative is fairly high, which can allow her to get into a beneficial position because she would go near the top of the order.  But sometimes it’s worth delaying in order to assess the situation and determine where the real threats and opportunities lie.  Even if I can act first it doesn’t mean that I always should.


Prepare, then improvise.  “Hold lightly to goals and firmly to intentions,” as Pixar President Ed Catmull states in his book Creativity, Inc.: The GM’s job is to create the campaign – the main quest, the side adventures, all the characters the company needs to meet to get information, all the creatures the players will have to fight.  Many times a GM will have a plot line painstakingly developed, but if the players decide to turn left at the crossroads instead of right, that whole plot line goes unused.  As someone who likes to plan and ferret out all potential challenges through advanced trouble shooting, I know it can be hard to let go when the group decides to go in a different direction.

Along those same lines, people are motivated by different things that you.  Sometimes when you think everyone’s on the same page, you’re not, and it’s important to not make assumptions about what motivates people.  The best creative thinking, however, often comes from people who have motivations and points of view different from yours and it’s important to understand those two key factors when trying to accomplish a task.

Share information strategically. I know my character’s backstory and the information my character hears.  I can choose if, how, and when I share that information with my fellow players.  It has made me aware of the ways I can motivate others, depending on how and when I share information.

Bonding is important.  I can sometimes get too focused on getting things done and don’t leave time for building the social bonds that will help the teams I work with be more efficient.  A good leader learns when to allow the space for that, and our GM did just that after a particularly difficult combat.  Our GM knew we were about to head into an even more challenging combat, so he allowed us the space to grow our character’s interplay in ridiculous ways before we traveled into the new challenge, and I’ve never laughed so hard.  Months later, we still reference the jokes that came out of that “night” our characters spent stuck in a lean-to in a downpour.

When you need to invest in others you end up also working to create the circumstances that allow them to shine.  This is akin to the idea of basketball or hockey “assists” – where the person who gets the ball/puck to the goal-scorer is given credit for setting up the shot.  When you are invested in your teammates you are more likely to think about how you can influence the circumstances to set up your partners for success.


Step into another’s shoes. By role-playing a character that has different skills, emotions and reactions than I do I’m forced to think about how my character would act in a situation.  What might set Trig off?  What might she get excited about?  Who does she trust?  How do her abilities help her to achieve her goals?  These are questions I can ask myself in all my interactions with people to build understanding.

I can change the story line.  At any point, my actions can change the narrative I’m in.  I just have to lobby hard enough for it.


To run a successful campaign, you have to nurture it and the people involved in it.  Our GM is particularly talented and creative – not just because he knows the rules inside and out, and not just because he puts in hours creating the adventures and the creatures that our company meets along the way.  What makes our GM talented and creative is that he also operates as a mentor and teacher to each of us.


He is expert at pushing us when we get bogged down in the rules or need to form better role-playing habits (like not stopping the action constantly to ask questions).  As I mentioned above, he knows when to give us the time to bond as characters.  He also crafts and introduces scenarios into the storyline that enable the players to practice or grow certain skills, and to put each one of us in a leadership position in different scenarios.  He invests time, as he did with me and my combat skills, to work collaboratively to address the weaknesses of players.  He also regularly asks for feedback on how the session went and how he can better support us, he makes changes, and gives rewards.  It’s been a true education watching him mold and support our team to achieve success.


There is rampant creativity, artistry and innovation at every turn in my experience of Dungeons & Dragons, and it has deeply influenced how I view issues that come up in my life and work.  Playing has also increased my creative agility.  So as we sit around in our living rooms these next couple of weeks, perhaps planning our New Year’s resolutions, maybe it’s time to dust off the old board games or embark on learning something new, something un-digitized.  My resolution is to remember how important it is to play, to risk doing something I don’t fully understand, and to gather together people who share my joy in creativity.  And who knows?  I may just roll a natural 20.



Kacy O’Brien is the Program Manager at Creative New Jersey, a statewide initiative dedicated to fostering creativity, innovation, and sustainability by empowering cross-sector partnerships in commerce, education, philanthropy, government, and culture, in order to ensure dynamic communities and a thriving economy.