Designing the adventure

From the basement to the boardroom: A dungeon master's guide to human-centered design
Wednesday, June 5, 2024
Author’s Message:

I grew up playing one of the most well-loved (and misunderstood) games of our time—Dungeons and Dragons. Popularly referred to as D&D, the premise of the game is simple: each player assumes the role of a unique character in a fantasy world and joins with other players (in person, around a real table) to seek adventure and fortune. A Dungeon Master (also known as the DM) facilitates and narrates the adventure, improvising with the players who must use their character’s skills (and their own wits) to overcome whatever challenges befall them. Whether reclaiming a lost treasure from an ancient dragon (think J.R.R. Tolkien’s The Hobbit) or saving a village from marauding raiders, the point wasn’t always to “win” as in most games, but to enjoy the adventure as it unfolded. For the majority of my time playing D&D, I was the Dungeon Master. As the DM, I built the world in which the characters lived (and sometimes died); constructed the adventure, set the scene and engaged with the players (often as another character) and watched the players (my friends) interact as the story unfolded. I loved all of it.

Little did I know at the time that I would establish a company in which the skills I developed playing D&D would help teams at some of the world’s largest organizations navigate challenges and co-create solutions. Consultant-strategists at Territory essentially play the role of DM for our clients. We help them clarify what “winning” looks like; identify the players and skills needed; plan and facilitate the journey for the team; and use our experience and expertise to navigate and adjust as needed to help them arrive at their desired goal. 

I hope you enjoy the adventure.
Matt Morasky
Partner and co-founder, Territory, Inc.

Designing the Adventure

For most people (and certainly for gamers), the promise of immersing yourself in an experience outside of your daily routine, one that fires your imagination, tempts you with riches and power and challenges your resourcefulness, is a welcome adventure. Sadly, in the gaming world (and in our daily lives), many of us have seen these promises fall far short of the mark. Whether an awful experience or simply a dumb game, the source of failure is almost always the same: poor design. I first learned this lesson in my early teens, as a Dungeon Master trying to create the ultimate fantasy adventure for my friends. The game was extremely well designed, but the players’ experience of it depended entirely on my ability to plan an epic adventure. Believe me when I tell you that a group of teenage friends will tell you without hesitation how far you fell short of the mark. With an audience like this, I quickly learned the importance of extensive preparation.

Today, in my work at Territory, ensuring the client team reaches their goal and gets the most out of the experience still requires thoughtful planning. As you might expect, more time goes into understanding the end goal, identifying who is playing and what activities are best suited for the team to succeed than is actually spent in workshops. Three elements are as essential today as they were then: the goal, the party and the path.

The Goal

Players, just like clients, are almost always focused on the end goal or completing the quest. Sometimes, the goal was clear. For example, defeating a powerful enemy to retrieve a priceless magical artifact. At other times, the objective wasn’t so clear. Players started the game with a vague notion that they would “seek their fortune beyond the borders of the kingdom.” Whether their destination was immediately apparent or not, players always rallied around a collective sense of purpose. The DM’s job was to learn about the player’s purpose, provide them with a specific quest and steer the party toward it, or allow players to find their own way.

Today, we begin the planning process by asking our clients “What does success look like?” We ask this not only because it defines a clear deliverable or milestone but because it also establishes a sense of purpose. Whether executives in the boardroom or friends in my basement, people inherently want to be motivated to take action and get excited about what it will mean to finish.

The Party

Dungeon Master: “Your small boat is suddenly surrounded by creatures who are half human and half fish. They are armed with tridents and appear to be beckoning you with high-pitched squeaks and clicks.” 

Player One: “I don’t think any of us speak ‘Merish’.  Do we have a magic user who could use a spell to translate?”

Player Two: “Ummm… Nope, we all chose to be fighters.”

In D&D, the group of players is called the party. Just like participants in workshops, each of them brings their own specific talents and unique experiences to the table.

But players are not just the sum of their talents. They are people with very different experiences, attitudes, and agendas. Under the pressure of “the game,” player relationships can become unpredictable, even volatile. Understanding the different skills, experiences, and attitudes of each player is essential. In our work, we always seek to identify the basics up front:

  • Who is coming on the journey with you?
  • What roles do they play?
  • What level of skills and experience do they have?
  • Have they worked/played this way before?
  • If so, how well do they work together?
  • What roles/skills/voices are we missing?

D&D was usually played with friends, so the answer to many of these questions was well known to me. In the business world, we are always working with new ‘players.’ Sure, we may get to know them during initial meetings, but we may not know how they behave around one another and what they really want to accomplish until we’re in the room together. The more you know about the players, the better you can work with them and adjust how you run the workshop to fit their needs.

One of the greatest satisfactions of being a Dungeon Master was making the game a great experience for everyone in the party. This involved providing opportunities and space for players to interact and explore problems together—leveraging their knowledge, skills, and experience to make decisions and move forward. Today, we don’t always know what chemistry the client team will have, but we focus on creating combinations and providing opportunities to build connections and confidence within the team so that they will become even better at the game while working toward their goal.

The Path

One of the biggest mistakes any DM could make was designing an adventure that didn’t fit the skill level of the players. While parties were eager to jump straight to the end (or leap directly into the dragon’s den), rarely were they ready to take on the final challenge straight out of the gate. A good DM knows how to develop a path that develops the right skills, provides the right tools, and instills the right amount of cunning that can be brought to bear to help the party overcome the challenges that lay between them and their much-desired treasure.

As we plan engagements at Territory, we also think incrementally. Once we know the type of journey we’re taking, we can define the steps and identify what we’ll need from the client participants and the most effective way to engage them to get it. We divide the stages of the engagement into activities, the activities into exercises, and each exercise into outcomes. Careful planning allows the team to focus on clear and right-sized tasks, the outcomes of which progressively contribute to reaching the end goal.

In a transformation journey, for example, the team must work to understand each of the audiences they seek to change. They may explore the lives and experiences of each audience to identify their unique barriers and accelerators to the change. Then, they might develop tools and training as well as calendars and communications that resonate with the audiences to help drive the change.

An incremental approach has the same impact on improving the odds of a junior product team developing a viable innovation strategy as it does a group of apprentice thieves stealing a treasure hoard from under an ancient dragon. As a DM, the range of possible encounters was limited only by my imagination. In business, we don’t have quite as much liberty, but we still have many engaging ways to approach workshop activities.

Incorporating drawing, movement, puzzles, even role-playing can create a productive, safe and fun environment for working. It all depends upon the creativity and resourcefulness of the facilitator. But even when we develop the most understandable, manageable and feasible path, it doesn’t mean the players will follow it.

Teams make their own choices, and sometimes, we must deviate from the plan to address unforeseen obstacles. The ability to react and facilitate in an impromptu manner, but still keep the team focused on the end goal is essential. Good planning is about knowing where the team needs to go and how to get there while also remaining open to unanticipated yet essential detours.


The similarities between preparing and planning for a D&D adventure and a Territory engagement are remarkably similar. Regardless of how much work you put into planning or how detailed your plan is, the golden rule remains: your plan and the path should always serve the ongoing needs of the party while flowing in constructive and cumulative ways.


The hours I spent preparing for D&D games showed me the value of hard work, the importance of thinking about how to engage with people and the joy everyone experiences when it all comes together. But perhaps the most valuable lesson was when I discovered that work, even an entire career, could be as fun and engaging as embarking on an epic adventure with your best friends.

Matt Morasky

Co-founder and Partner at Territory, Matt focuses on helping organizations approach, develop and execute co-creative solutions to strategic challenges of all kinds. A veteran visual thinker and consultant, Matt works shoulder to shoulder with leaders and their teams to provide the insights, skills and tools to keep pace with increased complexity and accelerated change. He is also co-author of The Art of Opportunity, a practical guide to identifying, developing and seizing growth opportunities through strategic innovation.

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