5 Leadership Lessons from Dungeons & Dragons

The Dungeon Master in the popular fantasy role-playing game fills many of the same roles as a real-life leader.

DDI
7 min readApr 8, 2020

by Benjamin Shulman

Dungeons and Dragons (D&D) is a fantasy role-playing tabletop game that’s set in an imaginary world. The game, which has been around for nearly 50 years, tells the story of a party of adventurers.

It’s moderated by one player known as the Dungeon Master (DM), who is the main storyteller and acts out the roles of the “non-player characters” (NPCs). In the imaginary D&D world, these NPCs may be townspeople, monsters in the dungeon, or anybody not controlled by the other players in the game.

The DM also acts as the game’s referee, defining what the players can and can’t do, according the rulebook. For instance, a DM may say to the group, “Your party enters the tavern. The gruff-looking bar patrons halt their loud conversations and shoot violent stares at you. All is now silent except for the beating of your racing hearts. What do you do?”

The other players, meanwhile, each assume the role of a different fantasy character (e.g., a warrior, a wizard, or an archer.) and interact with the DM to work together to solve problems, gather treasure and knowledge, and even fight battles. Over a series of play sessions, the goal of the game is to create an epic and unique story. With quick wit and some lucky dice rolls, characters go on quests, delve into dungeons, and bring either harmony or ruin to their fantasy world.

What’s the connection between D&D and leadership?

You may be asking, what does D&D have to do with leadership? As a longtime lover of tabletop games and a graphic designer here at DDI, I started to naturally notice parallels between what I was learning at work about leadership and what I was witnessing during my campaigns of D&D.

I even went as far as to ask a group of my fellow tabletop game fanatics on Facebook what insights they had about how D&D relates to the business world-particularly to leadership, as DMs are considered the masterminds of the game, making for an easy comparison to how leaders run companies. I asked them what behaviors and skills they had witnessed DMs display that were positive or negative in advancing or hurting the gameplay.

I was astounded by the responses-and by how much D&D could teach us about leadership. Here are a few of the specific parallels that were mentioned, as well as some insights.

1. “Good DMs, like good leaders, let each player have their moments-moments to share an idea, a plan, a feeling, a success-to shine and have the chance to make a meaningful contribution.”

Creating an inclusive environment at work, where everyone’s opinions and thoughts can be shared in a safe atmosphere, is of utmost importance. Fostering this behavior starts with leaders because they set the tone for an inclusive workplace, acting as role models who exhibit the mindsets and behaviors at the heart of inclusion.

A good DM in D&D will often ask players that are not the de facto leader of the group what they would like to do in a certain situation. For instance, this may take the form of a trap in the dungeon that separates the leader from the group. The DM could cleverly put the player who is not as used to being the leader in the driver’s seat to make some big decisions for the entire group.

While developing leaders who operate with inclusive mindsets and behaviors will certainly impact a workplace for the better, remember that inclusion is only half of the equation-exceling at diversity is also key for your organization to see the full business benefits.

2. “Like a manager, a good DM should challenge players (employees) with difficult but not impossible odds, allowing players (team members) to fail as long as it isn’t truly fatal. People learn from mistakes, but you have to give them the opportunity to make them.”

This advice is paramount and especially relevant for C-level leadership teams, who may face a situation where they need to fill a leadership position fast, and quickly get that person ready to staff and manage a team to solve critical business issues.

Accelerated development is key here, and part of that development should include getting the individual involved with senior leaders who are solving real problems today and enlisting that leader-in-training to help solve those business challenges. That way, learning and growing happen simultaneously. Part of this learning/growth opportunity includes the opportunity to experience failures.

In D&D, character death in the game is very common, but a good DM will let players “reroll” their characters when they fail. Just as a good manager will give their team the chance to learn from their mistakes and come back with a smarter solution the next time.

DDI’s book, Leaders Ready Now, dives further into the tactics for readying leaders quickly. The book’s introduction touches upon the importance of exposing leaders-in-training to failure during their development. This shouldn’t be isolated failure, but rather failure that’s shared. And that’s the key-shared failure usually isn’t fatal because there’s an opportunity to glean lessons learned from risky assignments together as a team. The opportunity to struggle through failed attempts and then come back again to try different, hopefully better solutions, with support along the way, is a great way to give your leaders-in-training the insight they need to be ready to take on stretch assignments.

3. “Both managers and DMs need to be fair and treat everyone equally. The fastest way to sow disharmony is to play favorites.”

Nothing can build resentment among the players faster than a DM showing favoritism. A DM that puts one player and their character on a pedestal creates conflicts and causes confusion that can impede the group’s progression in the story. Playing favorites also can do the same thing in the workplace. How many times have you seen someone get a promotion just because he is friends with the boss, or someone get hired because she went to the same university as the hiring manager? Check out some considerations for making sure your hiring processes are fair and free of bias.

Also, according to DDI research, people who feel they’ve been overlooked for development opportunities are more likely to leave the organization-and they could even go work for a competitor, which can certainly make things exponentially worse for the organization.

4. “You may want to lavish praise and treasure on your players/staff, but such things have to be done only when earned. Rewarding minor accomplishments with major awards sets low expectations and doesn’t push your gamers/staff to be engaged and do their best.”

Rewards in the workplace should be given when they’re warranted, because they can be an effective way to celebrate successes and create a high-performance culture. “Leveling-up” in D&D is the term used for growing a character’s skillset and attributes (e.g. strength and intelligence) and players do this by gaining experience points (XP). They can earn XP by slaying monsters or accomplishing quests or feats in the story. A good DM knows how much XP is enough so that players feel like they really earned it. The same way a good leader knows how to reward team members, so they feel engaged in accomplishing their goals and the mission of the organization.

Effective leaders should recognize good work consistently, but they also should deal with poor performers in a fair and consistent manner. This is critical to having a top-performing team and retaining the best people.

5. “Adaptive thinking is a skill both DMs and managers should have. When a DM’s story doesn’t go as planned or the players aren’t focused on the story that’s been created, DMs must adapt and be flexible. This includes when a player can’t make a session, or an employee can’t make an important meeting.”

With technology transforming elements of all realms of our lives, keeping pace and learning to weather changes gracefully as they’re forced upon us is a great skill for both leaders and non-leaders to have. Imagine a DM that sulks if the players are not able to make their proposed timeslot for games. Would you stick around with someone who is unwilling to change to accommodate your needs? The same goes for managers who set unrealistic and immoveable goals that their team cannot meet without hardship.

Being adaptable and flexible both in D&D and in the workplace includes being nimble and being able to respond both quickly and intelligently to changes-whether those changes are expected or not. This article from Forbes, “ 3 Characteristics of Adaptive Thinkers,” outlines the three qualities adaptive thinkers have, including curiosity, which “generates inquiry which wields problem-solving which finds results.” Leaders who are curious, adaptive thinkers are much less likely to remain rigid in their worldview, and much more likely to find the potential within themselves and in others.

Learn how DDI’s Interaction Management® can help your organization develop exceptional leaders.

Benjamin Shulman is a graphic designer at DDI. Previously, he was the owner and founder of Jelly Bean Soup Games, a game graphic design and consulting studio, contributing to such games as Tiny Epic Galaxies, Heroes of Land, Air & Sea, and Herbaecous. Benjamin is still an avid gamer and geek and is always ready to play a fun game with awesome people. Special thanks to Carly Barry for her help in writing this blog.

Originally published at https://www.ddiworld.com.

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DDI

DDI is a global leadership company that helps organizations transform the way they hire, promote and develop leaders at every level. www.ddiworld.com