Rolling for Initiative: How Dungeons & Dragons Taught Me Everything About Team Leadership
The Unexpected Training Ground
I never thought a game about pretending to be elves and wizards would teach me more about leadership than any management training I’ve ever attended. But here we are.
Growing up, Dungeons & Dragons was this weird thing you did if you had friends—which, honestly, I didn’t have a lot of. My best friend and I played these sort of solo-person adventures, just the two of us hunched over character sheets and dice on pumped up inflatable air beds in the living room. It wasn’t exactly the epic party campaigns you see on Critical Role, but it was still magic. Years passed. We got older. Eventually, we managed to rope in some other friends, and now? Now we’ve got a whole group that gets together yearly, and those weekends have become something we all look forward to more than just about anything else.
What I’ve come to realize—and this took me embarrassingly long—is that every single thing I learned about managing data teams, facilitating retrospectives, and building psychological safety came from those gaming sessions. Not from the HBR (Harvard Business Review) or other MDA-style courses. From rolling dice and pretending to fight dragons.
You know what’s wild? There are over 50 million people playing D&D globally right now. That’s not a typo. Fifty million humans regularly sit down with friends to collaboratively tell stories, solve problems, and figure out how to work together under pressure. And researchers are finally catching up to what players have known all along—this stuff actually works.
When You Need Friends to Play
Here’s the thing about role-playing games that nobody really talks about: they’re ruthlessly social in a way that modern life mostly isn’t. You can’t phone it in. You can’t multitask through a combat encounter. You have to be present, engaged, and actively listening to what everyone else is doing, or the whole thing falls apart.
I think that’s what drew me in initially, even when it was just two of us. In D&D, you can explore these characters in a safe environment with people you trust. You can test out social dynamics—practice improvising arguments, working through conflict, expressing emotion—without any real-world consequences. It’s like having a sandbox where failure doesn’t actually hurt.
Glen Weldon, talks about discovering D&D as a closeted gay teenager in 1980s Philadelphia. He describes casting an illusion spell that made orcs believe they’d fallen into a pit of acid and spikes, causing them to die actual deaths from imaginary wounds. For just those few seconds, he felt cool. And when you’re going through “the deepest, most tortured throes of your closeted, excruciatingly awkward puberty,” that feeling matters more than you can explain to someone who’s never been there.
That’s what D&D does. It creates space for you to be someone else—someone braver, smarter, more confident—while simultaneously being more yourself than you might feel comfortable being in regular conversation.
The Science Nobody Knew They Were Doing
Let me tell you about some research that blew my mind when I found it.
Researchers at College of Charleston ran an actual study where they had college students play D&D campaigns with embedded moral dilemmas—including scenarios about torture, which is about as heavy as it gets. They measured the students’ moral development before and after using validated psychological instruments. The results? Significant growth in moral reasoning that wasn’t replicated in control groups who didn’t play.
Their conclusion: “Imaginative role-play gaming structures can function as an engaging, interactive ‘moral training ground,’ a medium that promotes moral development.”
But it gets better. A comprehensive 2024 review analyzed 51 papers from the past decade and found that tabletop RPGs provide benefits for cognitive skills, psychosocial development, stress prevention, and even therapeutic intervention for social anxiety, depression, and autism spectrum disorders. Empathy development happened in two ways—toward other players and toward fictional characters. Social skills improvement was the most common outcome across basically every study they looked at.
Dr. Sarah Lynne Bowman from Uppsala University has been researching this for years, and she’s found that role-playing games encourage creativity, self-awareness, group cohesion, and what she calls “out-of-the-box” thinking. These aren’t just soft claims from enthusiasts; this is peer-reviewed academic research showing measurable improvements.
There was even a study tracking six subjects with autism spectrum disorder across 12 months of RPG sessions. After six in-person sessions, mean frequency scores for social interaction increased while difficulty scores decreased. One participant said: “After trying the tabletop RPG, I like to talk more than before.”
That’s the kind of thing you can’t fake. That’s real human development happening through collaborative storytelling.
The Pandemic Proved Something
When COVID-19 hit, something interesting happened. Search interest in D&D jumped 85%. Sales increased 33%, making 2020 the most successful year ever for the game. And a theology professor named Emily Hunter McGowin—who’d been taught during the Satanic Panic era that D&D was basically evil—found herself becoming a Dungeon Master for her family.
She writes about how e-learning during lockdowns became “remarkably difficult. Motivation was low, and joy seemed nonexistent.” Her son asked, “Why not play D&D together?” So they started playing every Saturday, her husband, her friend, and their two oldest kids.
After two years, when her daughter’s character Navarra died unexpectedly, “a few of us wept openly around the table.”
Think about that for a second. They cried over a fictional character dying in a game. Not because they were sad the game was over, but because they’d invested so much emotion and connection into this shared story that losing a character felt like losing something real.
McGowin concluded: “I never thought we’d become a ‘D&D family,’ but now I can’t imagine our life without it.”
That’s what isolation does—it makes us realize what actually matters. And apparently, what matters is sitting around a table with people you care about, telling stories together, and creating something that exists only in your collective imagination.
Every DM is Secretly a Project Manager
Kane Hadley is a software development team lead who’s also a Dungeon Master. He’s got this great line: “Everything I know about project management I experienced playing Dungeons and Dragons.”
When he first took on project management responsibilities, he thought, “How hard can it be?” Then he realized that the people who’d been doing it before were actually working incredibly hard to make everything run smoothly, and he just hadn’t noticed.
Here’s what he learned from DMing that transferred directly to managing projects:
You can’t just wing it. When you start playing D&D, you might think, “Let’s just play out the first session and figure out the rest as we go.” But once you try that, you realize why planning matters. You need to figure out what needs to be done and how to get it done. There’s a business need you’re designing a solution for, and the team needs to understand the overall strategy so they can make good local decisions.
Communication has to be crystal clear. Early on, Hadley had his story in mind but didn’t communicate it well. He expected to just say some things and the players would understand what he wanted them to do. Very quickly, he realized they couldn’t read his mind. He needed to be clear about the direction so everyone understood. Same thing with project teams—you want to encourage and empower them by giving clear instructions, but you don’t want to micromanage. You want them to feel empowered, but not like they can just go in any direction. There’s a balance.
Motivation matters more than mandates. In D&D, you need to motivate your players to want to continue playing. It’s a long game, and they could get bored or decide not to show up anymore. Same with team members—you want to motivate them to not just complete tasks, but to do the work effectively and exceptionally. You want to give them confidence to learn and grow. You want to bring the best out of your team, not just extract the minimum.
These aren’t abstract leadership principles you memorize from a textbook. They’re lessons you learn viscerally, through experience, when you’re trying to keep six players engaged in a story where their characters might die and they have to actually care about the outcome.
The Class System is Actually Genius
One of the smartest design choices in D&D is the class system. You can’t have a party of all wizards and expect to survive. You can’t have all tanks and expect to solve puzzles. You need diversity—not because it’s politically correct, but because the game mechanics literally require it.
Tanks absorb damage so the squishy casters don’t get one-shotted. Casters deal area damage and control the battlefield. Healers keep everyone alive. Skills specialists handle traps, gather information, and sweet-talk NPCs. No single character can succeed alone.
This creates functional interdependence. You have to cooperate. You have to understand what everyone else brings to the table. You have to develop strategies that leverage complementary strengths.
Sound familiar? It should. That’s exactly what good data teams do. You need people who can write SQL and people who can communicate findings. You need folks comfortable with ambiguity and folks who insist on rigor. You need engineers who build pipelines and analysts who understand the business context. The diversity isn’t just nice to have—it’s functionally necessary.
Laura Comacho from the Mixonian Institute puts it well: “Getting to know your colleagues at a deeper level through creative activities creates the space to build trust. The goal is for everyone to feel encouraged to speak up.”
Or as one team-building consultant says: “The beauty of a well-balanced team—or adventuring party—is that individual weaknesses are overcome by collective strengths. Just because you’d never send your barbarian to negotiate a peace treaty doesn’t mean she’s not the best head-smasher on the team.”
Active Listening or You Die
Here’s a rule I’ve noticed in every successful D&D group: you have to pay attention even when it’s not your turn.
The battlemap changes constantly throughout combat. You need to adapt your tactics to match. If you zone out and then spend five minutes on your turn figuring out what to do, everyone gets annoyed. More importantly, you miss opportunities to support your teammates, combine abilities for better effects, or prevent someone from making a terrible mistake.
This translates directly to data teams. How many meetings have you sat in where people are clearly not listening? Where someone asks a question that was literally just answered two minutes ago? Where people are thinking about their own agenda instead of engaging with what’s being discussed?
In D&D, that behavior gets punished immediately. Your party wipes because you didn’t hear the DM describe the hidden trap. Your friend’s character dies because you didn’t realize they were low on hit points and needed healing. The consequences are fictional, sure, but they’re immediate and social—everyone knows you weren’t paying attention, and they’re frustrated.
Best practices from experienced players emphasize: “Learn their stories. Boost their characters. You might notice and point out an opportunity for another player to show off their skills, share their backstory, or achieve a major objective.”
Imagine a rogue and a ranger tracking gnolls through the woods. The rogue could ask to make a Survival check to track the horde himself—or he could ask the ranger to lend her expertise. When players shine the spotlight on others, they strengthen the bond between characters, improve the party’s ability to achieve goals, and deepen collaborative storytelling.
That second option—asking the ranger for help instead of doing it yourself—that’s the move that builds teams. That’s what creates psychological safety and trust.
The “Yes, And” Principle
Here’s something I stole from D&D that I use in every retrospective now: the “yes, and” principle from improv theater.
The key to being a great D&D player isn’t telling your character’s story. The goal is to build something awesome with all your friends. That means when another player does something crazy or dumb, you don’t shut them down—you jump in and help them succeed.
Other than rare circumstances where someone’s about to derail the entire campaign, you should never try to stop another player’s actions or plans. You support them. You build on their ideas. You make them look good, even when their plan is objectively terrible, because the story of a terrible plan somehow working is way more interesting than the story of someone vetoing it before it happens.
I’ve run retrospectives where I basically turned the sprint into a D&D encounter. The work we did manifested as creatures or challenging environments. The ways the team countered those challenges became their character abilities and tactical decisions. When someone said, “This bug was really frustrating,” I’d describe it as a monster with specific attack patterns. Then I’d ask, “How did you damage it? What abilities did you use?”
It sounds silly written out like that. But it worked. People who normally stayed quiet in retros started jumping in with creative descriptions of how they solved problems. The metaphor gave them permission to be playful and take risks. The gaming frame made it safe to admit mistakes because, hey, everyone’s character fails saving throws sometimes. To this day, people still remember it as one of more fun retros they have had.
Corporate America is Finally Catching On
So here’s the thing that blew my mind: actual companies are now using D&D for team building. Not small startups. Big companies.
HashiCorp’s VP of Developer Relations created a custom D&D campaign called “The Tower of Hashi” for their community team offsite. Each floor of the tower themed around their products and company philosophy. They made it open-source so other companies could use it. The team’s feedback? “It was great for the rest of us, who wanted more time together engaging in conversation… exploring a darkened tower, solving puzzles, cracking bad technology jokes, and battling monsters.”
Code & Theory in One World Trade Center runs bi-weekly D&D game nights for developers, designers, and digital strategists. A front-end developer there says: “My role at work is not social. Playing D&D gives me a chance to talk—make stuff up, in fact—and BS with coworkers.”
NBC Universal’s Senior HR Manager observes that D&D “breaks down the barriers people put up at work” and allows interaction “in a different way.” Amazon’s Head of Alexa Games Marketing recognizes the value of “short-term D&D sessions” for achieving team goals through role-playing.
There are even professional DM companies now that specialize in corporate events. They’ll come to your office, bring all the materials, and run custom adventures designed to develop specific skills your team needs. Some of them work with Sony, Amazon, and Deloitte. They’ve run games for teams ranging from 3 to 300 people.
The really interesting part? Research shows 83% of employees who experienced gamified learning were more motivated. 72% felt gamified elements inspired them to work harder. 90% felt it made them more productive. Knowledge retention increases 30% with gamification versus traditional methods.
That’s not just correlation. That’s measurable improvement in outcomes that companies actually care about.
The Skills That Transfer
Let me get specific about what skills developed through D&D actually transfer to professional contexts:
Communication: You learn active listening by having to understand party members and develop strategies together. You practice clear articulation by explaining ideas to advance the narrative. You improve verbal confidence through role-playing. You get better at real-time response in dynamic, high-stakes situations.
Teamwork: D&D is inherently cooperative, not competitive. You learn to leverage complementary strengths. You develop a shared success mentality—a rising tide lifts all boats. You understand interdependence viscerally because splitting the party is basically a death sentence. You build trust by relying on each other’s unique abilities.
Leadership: Everyone takes leadership roles at different times. The structure is adaptive and flexible. You make decisions under pressure with limited information. You learn to inspire others by rallying party members toward common goals. As a DM, you develop skills in managing groups, organizing experiences, and facilitating discussions.
Problem-solving: There’s no set path to victory. You can approach problems from infinite angles. Lateral thinking gets rewarded. Strategic planning matters because you need to anticipate outcomes and formulate plans. Adaptability is crucial because your first plan will definitely fail. Risk assessment improves because you’re constantly analyzing options with incomplete information.
Trevor Kincy, a founder who writes about this stuff, makes a great point: “Because unlike other team building exercises, D&D necessitates that everyone involved pretends to be someone else—making it much easier to self-reflect and be open to new ideas.”
The problems the party faces aren’t mundane or tedious—they’re exciting, sometimes terrifying, sometimes desperate, sometimes hilarious. When your (pretend) life and your teammates’ (again, pretend) lives are on the line, the lessons you learn stick that much more than a typical team-building exercise.
What the Research Missed
For all the studies proving D&D develops skills, there’s still a lot we don’t understand. Nobody’s done longitudinal studies tracking the same players across multiple campaigns to see if skills compound over time or plateau. We don’t have comparative studies of different RPG systems to identify which mechanical features most effectively develop specific capabilities. Does Pathfinder’s complexity build different skills than D&D 5e’s streamlined approach? Probably, but we don’t have data.
We also don’t know if benefits translate equally across different cultural contexts. Gaming culture in Japan looks different from gaming culture in the US, which looks different from gaming culture in Brazil. Do the social skills you develop transfer the same way?
But honestly? I’m not waiting for more research before I keep using these techniques. The evidence I need is sitting in my retrospectives when quiet team members start speaking up. It’s in the Sprint Reviews where we’re all genuinely excited about what we built together. It’s in the one-on-ones where people tell me they feel heard and supported.
The Dice Keep Rolling
Here’s what I’ve come to believe: D&D succeeds where traditional training fails because it smuggles the lesson inside the fun. You’re not sitting through a PowerPoint about the importance of active listening. You’re trying to figure out how to defeat a beholder, and you miss the crucial detail your teammate mentioned, and your character gets disintegrated, and everyone learns the lesson without anyone having to make it explicit.
The game creates low-stakes environments where you can experiment without real consequences. You can attempt creative solutions, fail spectacularly, analyze what went wrong, and try again. The worst outcome is fictional character death, not actual career damage. That safety enables risk-taking and learning in ways that real work environments rarely permit.
When Emily Hunter McGowin’s family wept at Navarra’s death after two years of Saturday sessions, when Glen Weldon felt cool for fleeting seconds during tortured adolescence, when Kane Hadley realized everything he knew about project management came from DMing—these moments reveal D&D’s essential function: creating space for humans to collaboratively imagine, fail safely, support each other, and emerge changed.
I think about my own yearly gaming weekends now, and I realize they’re not just fun—though they are absolutely that. They’re also maintenance. They’re how I practice being present, how I remember what collaboration feels like when it’s working, how I stay sharp on skills that atrophy when I’m stuck in back-to-back Team’s meetings.
The stigma has dissolved. The Satanic Panic is over. The question isn’t whether D&D provides value—the research confirms it does, repeatedly, across multiple domains. The question is how to optimize its transformative potential across contexts.
So yeah. I love role-playing games. And I’m not remotely embarrassed about that anymore, because I’ve seen what they do. I’ve watched shy team members become confident contributors. I’ve watched conflict-avoidant engineers practice having difficult conversations. I’ve watched data analysts develop intuition about storytelling and narrative structure that makes their presentations dramatically more effective.
The dice keep rolling. The story continues. And the real-world benefits accumulate—one session, one character, one collaborative decision at a time.
Maybe it’s time to stop calling it a game and start calling it what it actually is: one of the most effective training systems ever accidentally designed for developing the exact skills that humans desperately need in the 21st century.
Initiative has been rolled. Your turn.
References & Further Reading
Research Studies:
Wright, J. C., Weissglass, D. E., & Casey, V. (2020). “Imaginative Role-Playing as a Medium for Moral Development.” Journal of Humanistic Psychology. College of Charleston.
Yuliawati, L., Wardhani, P. A. P., & Ng, J. H. (2024). “Benefits of Tabletop Role-Playing Games: A Scoping Review.” Universitas Ciputra Surabaya and IMU University. Analysis of 51 papers, 2013-2023.
Bowman, S. L. (2010). The Functions of Role-Playing Games: How Participants Create Community, Solve Problems and Explore Identity. Uppsala University, Sweden.
Henning, et al. (2024). “Social Skills Development Through RPGs in Autism Spectrum Disorder.” University of São Paulo. 12-month longitudinal study tracking 6 subjects.
Spinelli, L. (2018). “Creativity and Tabletop Role-Playing Games.” Pace University. Study of 85 participants aged 18-25.
Chung, T. (2012). “Table-top Role Playing Game and Creativity.” Thinking Skills and Creativity, using Wallach-Kogan Creativity Tests.
Rivers, et al. (2016). “Empathy and Fantasy Role-Playing.” Research on empathically-imaginative style in role-players.
Abbott, et al. (2022). “Tabletop Role-Playing Games as Therapeutic Interventions.” Social Work with Groups. Research on social anxiety, loneliness, and depression.
