What if stepping away from reality gives us a better way to practice dealing with it?

Think about the last time you were in a meeting where someone had a terrible idea.

Did you speak up? Did you stay quiet? Did you try to diplomatically steer the conversation in another direction?

Now imagine that same situation, except you're a wizard, your colleague is a barbarian, and the terrible idea involves negotiating with a dragon who has already eaten three diplomats.

Suddenly, the stakes feel a little different.

You might be more willing to challenge the plan. To take a risk. To try something you wouldn't normally do.

And that's where things get interesting.

Because sometimes we need to step outside our everyday reality to see how we behave inside it.

At work, we're constantly navigating invisible pressures.

We want to be respected. We don't want to embarrass ourselves. We worry about how our colleagues perceive us. And we certainly don't want to damage relationships with people we have to see again tomorrow.

These concerns aren't irrational. They're part of navigating professional relationships.

But they can also make it difficult to experiment with new behaviors.

A manager who wants to become more collaborative may struggle to relinquish control during an important meeting.

An employee who wants to speak up more often may hesitate when a senior leader is in the room.

Someone who avoids conflict may understand the importance of healthy disagreement but still find it incredibly uncomfortable.

Traditional leadership training can explain why these behaviors matter.

But understanding a behavior and practicing it are two very different things.

That's where tabletop role-playing games offer an interesting opportunity.

In games like Dungeons & Dragons, participants step into fictional roles and work together to navigate an unfolding story.

They might be a charismatic bard, a cautious wizard, a fiercely protective paladin, or a barbarian whose preferred negotiation strategy involves a very large axe.

Each character brings different strengths, limitations, and perspectives.

And participants make decisions on their behalf.

Here's the interesting part: Playing a character can create some distance between a person and their everyday professional identity.

When you're pretending to be someone else, experimenting with unfamiliar behaviors may feel less personally risky.

A quiet employee might try being the person who leads the conversation.

A manager who usually takes charge might practice stepping back.

Someone who tends to avoid disagreement might explore what happens when they challenge a decision.

Not because they're being told to change their personality, but because the fictional situation gives them permission to try something different.

This doesn't mean a game automatically changes someone's workplace behavior. But it can create opportunities for experimentation that might be harder to arrange in an ordinary meeting.

Imagine bringing five managers together for a professional development experience.

Their mission sounds simple.

A village is in danger. Resources are limited. Information is incomplete. And they need to agree on a plan before time runs out.

Nobody has a script. There's no single correct solution.

Within minutes, familiar patterns start to emerge.

One person takes charge before anyone else has spoken.

Another immediately starts evaluating risks.

Someone tries to keep everyone happy.

One person wants to act immediately. Another insists they need more information.

And someone with an excellent idea can't seem to find an opening to share it.

Sound familiar?

The village might be imaginary, but the group dynamics are very real.

Participants are making decisions together, negotiating priorities, responding to uncertainty, and figuring out how to work with people who think differently.

The fictional setting gives them a shared experience they can examine afterward.

And that's when the real professional development begins.

At Once Upon a Roll, we use tabletop role-playing games as a foundation for experiential leadership development.

But we're not simply gathering coworkers around a table and hoping that playing D&D will magically make them better leaders.

Our experiences are intentionally designed around workplace challenges.

And while participants are navigating the adventure, a trained facilitator is paying attention to how the group interacts.

Who gets heard?

Who makes decisions?

How does the group respond to disagreement?

What happens when a plan fails?

Does anyone notice when a teammate is being left out?

These observations become the foundation for a facilitated conversation after the game.

We might ask:

Sometimes, a conversation about a fictional village reveals something important about how a real team functions.

And because everyone experienced the same adventure, they have a shared reference point for discussing it.

Instead of saying, "Our team needs to communicate better," they can talk about the specific moment when three people had different ideas and nobody stopped to listen.

That's a much more useful place to begin.

There's a reason professional development can't rely on information alone.

Think about learning to ride a bicycle.

You could attend a lecture about balance. Read a book about steering. Watch someone demonstrate proper technique.

All of that information might be useful.

But eventually, you have to get on the bicycle.

Leadership skills are similar.

We can teach someone the principles of active listening, emotional intelligence, or collaborative decision-making.

But developing those skills also requires practice.

Educational theorist David Kolb's experiential learning model describes learning as a process involving concrete experience, reflection, conceptual understanding, and experimentation.

In other words, we learn not only by being told what to do, but also by doing something, thinking about what happened, and applying what we discover.

Tabletop role-playing games can provide a flexible environment for that cycle.

Participants encounter a challenge, make decisions, experience consequences, and reflect on their choices.

The value comes from connecting those experiences to situations outside the game.

One of the most useful things about fictional scenarios is that they allow us to explore recognizable workplace challenges without recreating an actual workplace conflict.

Imagine asking a team to discuss a recent meeting where people felt ignored.

That could be a productive conversation.

It could also make participants defensive, especially if the meeting involved their manager.

Now imagine discussing a moment during an adventure when the group's wizard had important information but nobody listened.

The group can examine the interaction without immediately assigning blame for a real workplace incident.

That psychological distance may help participants reflect more openly.

Of course, an imaginary setting doesn't guarantee psychological safety. Skilled facilitation, clear expectations, and respect for participants' boundaries are still essential.

But fictional situations can create another way into conversations that might otherwise feel uncomfortable.

And sometimes that change in perspective is exactly what a team needs.

Most professionals already know they should communicate clearly, listen to different perspectives, and work collaboratively.

The challenge isn't always knowing what good leadership looks like.

It's demonstrating those behaviors when the pressure is on, personalities clash, and the right answer isn't obvious.

That's why we believe professional development should create opportunities to practice, not just opportunities to listen.

At Once Upon a Roll, we bring together purposeful storytelling, collaborative problem-solving, and facilitated reflection to help teams explore how they lead and work together.

Participants don't need to know how to play Dungeons & Dragons. They don't need to memorize complicated rules or have any previous experience with tabletop role-playing games.

They just need to be willing to step into a story, make some decisions, and get curious about what happens next.

Because the dragon isn't really the point.

The point is what happens when five people have to figure out how to face it together.

And what they discover about themselves along the way.

Bring a little adventure to your professional development.

Once Upon a Roll creates facilitated, tabletop role-playing experiences designed to help organizations explore leadership, communication, collaboration, and team dynamics.

If you're looking for a different way to help your people practice working better together, we'd love to introduce you to our world.

Learn more about Once Upon a Roll and our experiential leadership development workshops.