Dungeons & Dragons & Design

Why a campaign of “Dungeons and Dragons” could be your next team event.

This isn’t where I thought I’d start with my first Medium post, but here I am.

Dungeons & Dragons.

Or as we call it on our weekly calendar invite: “Dn🐉”. I used to play Dungeons and Dragons as a teenager, against most social norms at the time and loved every second. After a twenty year hiatus I find myself in love with the game all over again: the role-playing, the shared world building, the magic, the monsters and most of all the built up camaraderie between people. The game is experiencing a resurgence as of late.

Image for post
Image for post
Stranger Things — “Demogorgon!”

Metromile Does Dragons (actual name of campaign)

Image for post
Image for post

About halfway through our third session, I had this light bulb moment about Dungeons and Dragons and Product Design: both are fundamentally about problem-solving. The success of the group of adventurers in Dungeons and Dragons relies on a high level of collaborative problem-solving. Great design is accomplished with highly collaborative teams.

Once that “aha” moment set in I realized how powerful of a bonding activity this was beyond the laughs, bloody goblin battles, hidden treasure, and good conversation.

We are becoming a stronger team.

When the game stops for the night someone updates our slack channel about our adventure in Phandalin. You see, some bandits are terrorizing the town, and everyone is searching for this map, and a dwarf was kidnapped, etc.

The next day at work people might act out things that happened the night before. Inside jokes pop up — whether it is about Haela the Ranger’s murderous tendencies (don’t mess with her two short swords) or Zelphar the Bard’s ability to play the lyre and persuade anyone to do anything (he plays music in real life to set the mood).

Everyone is able to show a side of themselves that may not come out in a product design review or sprint meeting, happy hour, dinner, or typical team bonding event. It is the type of bonding that can only come organically. The team also gets to see me in a new light — quirks and all. When we are in the room together with a dungeon before us and dice in hand there is no manager/employee dynamic. Instead of talking shop we’re talking about if it is feasible to hurl a fireball across a chasm into a trio of unlucky goblins.

Our group is now seven game sessions in. Each ranging from one and half to three hours. From our short time adventuring together here are the three main parallels I’ve noticed between Dungeons and Dragons and Product Design.

1) Problem Solving

Another great team activity focusing on problem solving is to do an escape room. The thing that sets Dungeons and Dragons apart from an escape room is, typically, for an escape room there is one solution. In Dungeons and Dragons a problem can be approached from multiple vantage points. Much like the conceptual or discovery phase of a design project.

2) Variability

This variability leads to some actions working and others not. Because of this, the party has to adapt to the situation and try out new solutions. Thus, more dice rolls. Or more innovative creative thinking. Because sometimes the dice do not need to be rolled.

In cases where the players creatively outline how they will go about something the Dungeon Master can just allow it. For example, a character may say she is searching for a secret door by feeling at all of the cracks and crevices in the wall. Sounds like a creative way to solve the problem of finding that door versus just stating they are looking for secret doors. The game drives the players towards being creative, and fully thinking through how to best solve their given predicament.

Product Design is much the same. There aren’t dice, but there are end-users and customers, changing requirements (but hopefully not too often!), technical limitations, analytics, stakeholders, and other inputs. There are times, hopefully many, where out of the box, divergent thinking is going to drive the team towards the “right” solution.

The most successful product designers are able to adapt to this variability.

Image for post
Image for post

3) Design Teams Aren’t Made of One-Size-Fits-All Designers

Product Design is the same way: UX designers focus on end-to-end solutions; user researchers provide insights and broader understanding of the problem space; visual designers craft designs to pixel perfection; interaction designers meticulously fine-tune an experience; content strategists take complex problems and simplify them into well-understood labels, prompts, and copy.

Without the balance of all of those roles and skills, the resulting solution may not be as robust.

Image for post
Image for post
The Party, WizKids.com

Design Is Not a Silo

Having strong relationships with members of other functional groups is imperative to designing, building, shipping, and iterating on a solution. It can’t happen otherwise. So if you are a design team of one or two don’t let that stop you from trying this out with other people in your company.


I’ve been leading the Product Design team at Metromile for four years. Prior to that I led design teams at Salesforce and Autodesk. If there is something you are interested in learning more about let me know and I’ll give you my take.

Written by

Vice President of Product Design @ Metromile. Formerly Salesforce and Autodesk.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store