Your Workshop Needs More Dragons

What talking to from Dungeons & Dragons Masters taught me about running better workshops.

It was a quiet Friday evening in the agency basement when an account director took a longsword and sliced a goblin’s head off.

And no, this wasn’t one of the caffeine-dreams I sometimes have after working too long on a pitch. This was part of an office Dungeons and Dragons game — one we’d started having every couple of months. But as our party delved deeper into the dungeon, slashing trolls and facing down mind flayers, I realised I was a bit …distracted.

A bigger monster plagued my mind — the workshop I was about to run the following week.

Of all the crazy things strategists are often faced with, workshops have always seemed the scariest. You face a staggering number of obstacles — tight agendas, belligerent clients, overrunning interruptions, and an overall underlying sense of wankiness that permeates the whole affair.

And unlike my D&D character (a flaming demonic sorceress named Karen), I couldn’t just blast annoying clients out of the way with fireballs. Workshops made me feel a bit… powerless. But there was one person in the room who knew exactly what I felt — and she was sitting across the table from me, rolling dice in my face.

Meri, our Dungeon Master (and, in the daytime, account manager).

Every D&D game is led by a Dungeon Master, or DM. The DM knows the rules, creates the story, and works with you to develop your characters. But as the journey goes on, the DM must be led just as much as she leads. The players decide who they are, what they do, where to go, who to fight, what move to make.

And while she can uphold rules and keep them on track, the DM’s precious narrative is at the mercy of the players. She must adapt the narrative, reroute the obstacles, and rebuild the world and story (on the spot) with every new choice the characters make.

She’s not Tolkien delivering a novel — she’s a facilitator, running a workshop.

I realised then that the things we do when we run a workshop — managing people, moving things forward, setting them challenges, keeping everyone on the same direction — are the exact same things DMs are experts in.

So I spent the last month talking to DMs from across the world — and watching over 100 hours of D&D games through streams like Critical Role. Here’s what I’ve learned.

Starting the quest

Starting a workshop means diving into unknown (and often hostile) territory. A lot of your participants will see a workshop is typically a disruption to their work, a challenge to their opinions, with no clear outcome in sight. Having clarity is key. And DMs approach this with the same basic ingredients that fantasy storytellers use.

The Genre

There are as many types of campaign and story as there are DMs. And there are many tropes to choose from. A long, complex tale of political intrigue. A dark, spooky supernatural thriller. An epic LoTR-style adventure. It’s important for the DM to have an idea of the genre and type of story she’s telling.

In the same way, every workshop has different styles. Loose and free-flowing brainstorm, a structured and time-pressured sprint — decide what works for your style, and which you can best pull off as a moderator.

The Quest

Narratives can bend and shift, but in fantasy and D&D, there’s always a single set goal. Kill the dragon. Destroy the One Ring. Take the Iron Throne. In a D&D game, how you get there doesn’t matter, as long as you get there.

It’s the same in a workshop. You need to be crystal clear about what the goal is, what the scope is, and how each exercise gets you closer to that goal. The biggest killer of any workshop is ending without a clear outcome –the biggest motivator is starting with that ending in mind.

The Characters

In a D&D game, it’s important to know who your party is — and having a discussion with the party members is critical. Too many spellcasters and you’re vulnerable to blunt force. Too many healers and you won’t be able to do any damage. Again, it’s the same with workshops. Brand Team. Insights Team. Supply Chain. Content. Legal.

If you understand (and discuss) who’s coming to the workshops, you can make use of them, work around them and make them feel included.

After all, every person has their specialty, their own expertise to bring; consider using them as resources or point person whenever a related question comes up. But also give them the time to shine. Meri says she builds special parts in her games to give everyone a chance to play up their role and expand their backstories.

If I notice someone sitting a little in the shadows, I’ll purposefully give them mini-missions or single them out for non-lethal encounters. Sometimes I’ll take them aside and give them a secret mission which helps build up their sense of purpose and intensifies their involvement.

We can do the same: give different people roles, chances to speak, chances to contribute. Otherwise they’ll feel like background characters… and we all know nobody wants to be a sidekick.

Facing the monsters

The thing that makes workshops different from other strategic work is uncertainty. People will go on tangents, exercises will overrun, arguments will flare endlessly — shit gets pretty crazy. Luckily, DMs thrive on the uncertainty of a campaign, and they’ve developed tactics to deal with it.

Don’t be a Rules Lawyer

D&D has a complex web of rules and guidelines, and DMs have often had to learn an encyclopedic understanding of these rules. But quite often, they need to let those rules go — especially if it comes at the expense of simple, creative ways of solving a problem. Otherwise they end being what David Griner, Adweek editor and occasional DM, calls a rules lawyer.

I think the people who are flexible in the ways they engage with people, they’re the ones who succeed. Compared those who are really inflexible — if you’re very rigid about your expectations, if you’re very rigid about rules, if you’re a rules laywer.

In workshops, it’s important not to get too caught up in carefully crafted agendas. Quite often, you’ll realise that an exercise can’t happen without first addressing a previous issue, or that an exercise might not make sense at all for the brand you’re working on. Allowing those changes to happen is key to making your workshop work.

Prep branching

The best DMS adapt to those changes using something called prep branching. As DM Andi Ewington (famous for his animal-themed DM tweets) says, preparing for every eventuality can actually make players feel more free.

One word, ‘preparation’ — you have to think ‘branching’ whenever creating a story, get all those ‘what-if’scenarios crossed off. You won’t be able to cover everyeventuality, but having a good sense of direction just in case the party go left, instead of right will help give a sense of freedom to your players.

Great DMs do this by preparing in advance, understanding their players — or in our case, the client. more you know the client, the more you know what their issues are, the more you’ll be able to address those issues beforehand and match them if they come up.

Breathing room

DMs have what’s called breathing room characters — a reserve collection of side characters, and enemies that they can drop in at different points. If you get through a dungeon too fast, a DM can immediately drop in a set of trolls to slow you down. If you take way too long, she can instead drop in a helpful elf to guide the way.

In the same way, you can build breathing room into you workshop — have filler exercises prepared for workshops that are running too fast, and have fat in the agenda for workshops that are running over time.

Letting go

It can be tempting to judge a workshop by its smoothness, whether it finished on time, whether you crushed any participant arguments. But that’s not always what matters, and DMs know it too. As David says…

“It doesn’t matter if the players won the game, if they didn’t have fun doing it.”

In the same way, your workshop doesn’t lead to real, actionable work that has everyone included, then you haven’t done your job right. And yes, you can’t guarantee that clear, actionable work will happen. But that’s the point.

A workshop means, at its core, letting go, choosing collaboration over control. Because like all strategy, it’s not about you. As David says,

“They didn’t succeed because of you, they succeeded in many ways in spite of you’

But according to Andi, letting go is what makes the whole experience fun.

Feeling like a conductor who is about to let the orchestra run riot with the music — the chaos of the whole thing is exhilarating, especially when players suggest something which makes you think on your feet.

Workshops will probably always give me the shivers. But like any quest, there’s always a way through the dungeon, always a treasure chest after each dragon fight. And it helps knowing I can take inspiration from the DMs who deal with monsters in and out of the game.

Know your story, adapt to each challenge, and let go.

And if that fails, you can always grab a longsword.