Learning to Roll the Dice Later in Life

By Jennifer Tracy, C.I.M., C.Mgr. | Chartered Managers Canada

I came to Dungeons & Dragons in my 40’s, without the nostalgia many players carry from musty childhood basements and dog-eared rulebooks. I had no long-running campaign etched into my memory, and no beloved character I was resurrecting decades later. Instead, I arrived as an adult – initially hesitant but curious, even if quietly skeptical about what a fantasy role-playing game (RPG) could possibly offer someone already immersed in executive leadership, governance, and organizational life.

What I didn’t expect was how quickly the game would begin holding up a mirror to the leadership archetypes I've encountered in my career. 

Bravado, Caution, and the Leadership Spectrum

Playing alongside younger players like my nephew (my principle inspiration behind learning to play) has been one of the most instructive parts of this journey. He plays with unapologetic instinct and confidence, often acting before fully understanding the risk. He charges forward, narrates bold choices, and assumes that success is possible until proven otherwise. When things go wrong, he adapts and continues with renewed determination, his swagger never faltering.

My experience playing with adults could not be more of a contrast. Adults tend to bring their life experience directly to the table. We ask clarifying questions, debate probabilities and we hedge our bets. Our characters often reflect our professional conditioning: risk-aware, efficiency-driven, and outcome-focused.

In a recent campaign with adult players, our group of misfits were strategizing how to clear a mine of some unsavoury goblins. A lot of the planning felt like it was going in circles, so channeling my 11 year-old nephew's spontaneity, I made a suggestion: "We have war horses. Lets just light the wagon on fire and send them in." Not an elegant strategy, I admit. And while it was initially met with humorous guffaws and dismissal, the horses were eventually adapted as a key element of our insurgent strategy, to the great success of our quest. 

When it comes to either bravado or caution, neither approach is inherently better. In fact, the most effective moments in the game, much like in organizations, emerge when these approaches balance one another. Courage without strategy can be reckless. Strategy without courage can become paralysis.

Dungeons & Dragons doesn’t just allow these styles to coexist; it requires them to.

D&D Classes as Modern Leadership Archetypes

For the benefit of those who have not played D&D, each class represents more than a fantasy trope. It mirrors recognizable leadership styles we can see in modern organizations. What makes the game powerful is that every archetype has strengths, blind spots, and moments when it must rely on others. Let’s look at a few:

The Fighter - The Decisive Operator

Fighters lead from the front. They value clarity, action, and momentum. In organizations, this is the operational leader who excels in execution, crisis response, and delivery. Fighters remind teams that progress often requires action, not endless deliberation.

Leadership lesson: Decisiveness builds confidence, but unchecked action can outpace strategy.

The Wizard - The Strategic Thinker

Wizards plan, analyze, and anticipate. They manage complexity and long-term consequences. In the workplace, these are your strategists, analysts, and subject-matter experts; those who bring depth and foresight to decisions.

Leadership lesson: Strategy creates sustainability, but over-analysis can delay opportunity.

The Rogue - The Adaptive Problem-Solver

Rogues thrive in ambiguity. They read the room, spot hidden risks, and find creative workarounds. In business, this archetype shows up as the innovator, negotiator, or relationship manager - someone who navigates complexity with agility.

Leadership lesson: Adaptability creates advantage, but secrecy or independence can erode trust if misused.

The Cleric - The People-Centered Leader

Clerics support, heal, and protect the group. They are often underestimated until something goes wrong. In organizations, these are HR leaders, coaches, mentors, and values-driven managers who sustain morale and cohesion.

Leadership lesson: Culture and care are strategic assets, not “soft skills.”

The Bard - The Influencer and Communicator

Bards motivate through storytelling, humour, and emotional intelligence. They influence outcomes by shaping narrative and connection. In corporate life, these are communicators, facilitators, and change champions.

Leadership lesson: Influence drives alignment, but charisma without substance can falter.

The brilliance of D&D is that no party succeeds without a combination of these roles. Leadership is not about being the strongest class. It’s about knowing when to step forward and when to support someone else’s moment to lead.

Natural 20s, Critical Failures, and Psychological Safety

One of the most profound leadership lessons embedded in RPGs lies in how the game treats success and failure.

A Natural 20 is the highest dice roll possible and represents moments of exceptional success. But it doesn’t happen because the player planned perfectly. It happens because they took a chance. In organizations, breakthrough moments often come the same way: someone tries something bold, timing aligns, and momentum follows.

Consequently, a Natural 1 is an instant failure. Plans collapse. Outcomes go sideways and yet, critically, the story continues.

D&D teaches players that failure is not an endpoint. It’s data that simply opens doors to create new conditions, unexpected consequences, and sometimes even better stories. The table doesn’t shame failure; it incorporates it.

For teams, this is a powerful model of psychological safety. When failure is treated as part of the system rather than a personal flaw, people are more willing to experiment, communicate more honestly, and recover faster.

What Teams Can Learn from Playing RPGs

For adult learners and professional teams, role-playing games offer a rare combination of structure and freedom. They create a safe environment to practice leadership behaviours without real-world consequences.

Teams can learn to:

• Make decisions with incomplete information
• Balance speed and strategy
• Navigate conflict and competing priorities
• Share leadership dynamically
• Build trust through interdependence

Perhaps most importantly, RPGs remind adults how to engage their imagination again - not as escapism, but as a leadership skill. Creativity, empathy, adaptability, and narrative thinking are no longer optional in modern organizations. They are essential.

Rolling Forward

Learning Dungeons & Dragons later in life has reframed how I think about leadership. It’s shown me that experience does not need to dull courage, and that courage benefits from experience. It’s reminded me that leadership is rarely about having the right answer, and more often about creating the conditions for a group to succeed together.

Sometimes leadership looks like rolling a natural 20.
Sometimes it looks like recovering from a critical failure.
And sometimes, it simply looks like recognizing someone better suited in the moment and enabling their moment to shine.

All it takes is a table (boardroom or otherwise), a shared story, and the willingness to roll for initiative.

About the Author: 
Jennifer Tracy, C.I.M., C.Mgr., is an employee of CIM | Chartered Managers Canada for over 15 years as Manager of Communications and Administration. She has worked in finance, legal and administrative roles in Canada and England. Having a diverse career and educational background in legal administration, management, communications, and marketing, she has gained key insight into adaptive and forward-thinking management practices which inspire her submissions for the Canadian Manager magazine. Jennifer is new to the world of RPG and Dungeons and Dragons, but would like to try adapt its format into some future team building and leadership exercises - if that interests you, please reach out for how to get involved.