Tuesday Jun 10th, 2025

Rolling for Initiative at Work

It sounds kind of dorky

About a year and a half ago, a coworker casually mentioned that Dungeons & Dragons “sounded kind of dorky.” The funny thing wasshe didn’t actually know what it was.

At the time, we were chatting about my bi-weekly campaign with another coworker, and I realized something: she did enjoy fantasy. She had watched Game of Thrones and had just enough exposure to storytelling and worldbuilding to appreciate the genre. So I told herhalf joking, half serious“You’d probably love it.”

That offhand comment turned into something much bigger.

Starting Small: A Beginner-Friendly Adventure

We kicked things off with the Lost Mine of Phandelver starter campaign. It was something I had both played and run beforeonce even as the Dungeon Master for my son and his friendsso I knew it was a great entry point.

But I didn’t want this to feel like just another game. I wanted it to feel immersive, collaborative, and memorable.

So I added a few touches:

  • I built terrain maps using XPS foam to give encounters a physical, visual depth

  • I created custom character miniatures out of LEGO (a 2x2 base fits perfectly on a grid, which worked surprisingly well)

  • I helped everyone create their own characters, even if they had zero prior experience

What started as curiosity quickly turned into investment.

The Unexpected Outcome: Real Team Building

Over the course of about a year, we played through the entire campaign.

And something interesting happened along the way.

People who normally wouldn’t collaborate closely at work began:

  • Strategizing together

  • Solving problems under pressure

  • Listening to each other’s ideas

  • Supporting each other’s decisions

D&D naturally creates situations where success depends on teamwork. There’s no single “winner”only shared outcomes. That dynamic translated surprisingly well into how people interacted outside the game.

It wasn’t forced team-building. It just… happened.

Problem Solving in Disguise

Every session presented new challenges:

  • Negotiating with NPCs

  • Navigating traps and puzzles

  • Figuring out how to survive encounters that didn’t have obvious solutions

And the best part? There was rarely a right answer.

The group had to think creatively, adapt quickly, and sometimes recover from mistakes. Watching people approach problems from completely different anglesand then combine those ideaswas one of the most rewarding parts of running the game.

It’s the kind of problem solving you want in a workplace:

  • Collaborative

  • Creative

  • Low-risk but meaningful

Creativity as a Shared Experience

Once the group got comfortable, creativity really took off.

Players started:

  • Developing backstories

  • Making bold (and sometimes ridiculous) decisions

  • Thinking beyond “what’s optimal” and focusing on “what’s interesting”

As the Dungeon Master, I leaned into that energy. After finishing our first campaign, I began building a custom onepulling together elements from past games, favorite encounters, and original ideas.

The new campaign is set in Greyhawk and includes recurring characters and evolving storylines. But one of my favorite additions has been weaving in loosely inspired scenarios from real client experiences at work.

There’s something uniquely satisfying about seeing your team navigate a fictional challenge that mirrors real-world dynamicsonly with a bit more magic and a lot more fun.

Why It Works

D&D works in an office setting because it taps into things that traditional team-building exercises often miss:

  • Agency Players make meaningful choices

  • Collaboration Success depends on the group

  • Creativity There’s no single correct path

  • Engagement People want to participate

And maybe most importantlyit gives people something to look forward to.