Everything I Know about Worksessions, I Learned from Dungeons & Dragons

As the party approached Phandalin, they knew they were in for some heavy lifting. See, the town was overrun with Red Cloaks, and freeing it from the enslavers would not be easy. It would take more than sheer will. It would take strength, charisma and maybe a little luck.

Buckle up, y’all — we’re going in.

Forget what you think you know about Dungeons & Dragons, and please, put the cheap jokes aside. I’m talking about a multifaceted, collaborative game that is fully shaped by the people who play it. Fundamentally, it is about friends, storytelling, action, creative thinking and probability. What’s not to love, or at least respect?

Many people discover D&D as teenagers, but I was introduced to the game as an allegedly serious adult, so I had a fair amount of work experience by the time I began playing. As a result, I’ve come to understand that D&D can bring an exciting — even magical — perspective to that typically dry, boring professional experience: the worksession. In fact, these things have a lot in common.

So what can serious(ly bored) businesspeople learn from D&D?

A game is only as good as its Dungeon Master

Think of a Dungeon Master (DM in the biz) as the facilitator of the game. They set up narratives, articulate the mission and challenges, act as a point of reference for rules and occasionally punish players. However, a DM is not a manager or boss of the players. Rather, they enable player agency and allow people to control their own decision-making and storytelling. A good DM is empathetic, reading the room and guiding everyone with the right questions, hints and tools.

Considerations

• Do you have the right facilitator for your session?
• Is the facilitator properly prepared and set up for success?

Epic challenges require an epically diverse team

Who’s in the room matters. A room of wizards will always find a magical solution, a room of rogues will always find a sneaky solution and a room of bards will always attempt to sing their way out of trouble. However, the hardest puzzles in life and D&D cannot be resolved by a single skill set. They require a diverse mix of skills, backgrounds and perspectives. More than any other factor, who is in your party determines your party’s success.

Considerations

• Do you have the right people in the room to make informed decisions? Do you always turn to the same group or similar people?
• Who’s missing? How can you add additional perspectives or expertise to your session?

Make the mission explicit

A collective mission is what ties a party together. Beyond personal goals — like avenging one’s family or getting a raise — the big mission spans a campaign. You want success that goes beyond yourself by bringing justice to the region, stopping the Black Spider, slaying the dragon and meeting quarterly revenue projections. Your mission must be explicit (otherwise, how will you know what you’re doing?), but the method of accomplishing it shouldn’t be. That’s for the party to decide, together.

Considerations

• Can you articulate your team’s mission or purpose? Can your team?
• How can you make sure the short-term goal of your session ties back to your big mission?
• Are your team’s personal goals aligned with your overall goals?

A sense of closure

Like a great organization, a great game of D&D can last decades, but within that game there are a series of distinct campaigns and story arcs. There’s a balance of short-term and long-term goals, and a wise DM will guide a session by limiting the scope of play to the time allotted.

Few things are as frustrating as seeing smart, talented people spin their wheels for several hours without landing on a clear way forward. Proper planning, defined rules, effective facilitation and good old soft skills can ensure that every session ends on a note of accomplishment.

Considerations

• Beyond your overall mission, what is the mission for this specific session?
• Do we have the right tools, data, expertise, etc. in the room to make an informed decision?
• If not, can we map out a plan of action to get what we need?

Culture is critical

D&D can be as deep or shallow as its players want it to be. Some players are into very precise inventory management: “Come on, Rebecca, you can’t use your rope to scale the building! Your rope is only 30 feet long and the building is 50 feet tall.” Others prefer to focus on combat, in all its many forms. Still others are just looking for an excuse to tell ridiculous stories.

The collective mission is important, but alignment on how you play and prioritize the tasks at hand is important too. Your team can become frustrated when different players’ styles start pulling a session in opposite directions. Understanding different play styles, along with having a clear mission, explicit frameworks and a good facilitator can help navigate this challenge.

Considerations

• Who is going to be in the room? What are their “play styles”?
• Are there areas where the team may get sidetracked in unproductive ways?
• How can you best align and focus your team before the session begins?
• What frameworks and activities are most relevant to the goals and people involved?

Rules are meant to be broken

For any DM, the official D&D rules are just a jumping-off point. There are no D&D police (although I would watch the hell out of Law & Order: D&D), so it’s up to you and your party to figure out what helps you accomplish your mission. There’s more than one way to run a worksession, meeting or offsite. What matters is keeping an open mind and learning what works as you go. Don’t be afraid to start with some basic guidelines and then take off from there. Remember, it’s supposed to be fun.

While the rest of his party watched in amazement, Gunt Goodbarrel clambered up the decrepit tower at the top of the mountain. Without pausing for breath, he leapt, brandishing his knives and letting loose a fearsome howl, throwing himself on the dragon below.

When was the last time your worksessions had such adventure?

P.S. Okay, so Gunt ended up missing the dragon entirely (damn that die roll), but he was saved from the cold hard ground by a spell from Gem Glasshatter. Having a backup plan never hurts.

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This piece was made in collaboration with the amazingly talented Matt Lubchansky. Special thanks to my guild, you all rock (especially our DM Dan).