Storytelling for Architects, Tips from Unfamiliar Places



"Very literally, leadership is storytelling and leaders are storytellers"


Why tell a story: a story

I had just started a new position at a large healthcare company, and was invited pre-employment to attend a seminar and course being led by a technology leader; the focus and topic: Storytelling. This was an intriguing (and required) proposition, not only was I interested in storytelling as an art, but pretty fascinated with the motivations for this topic as well. I arrived in the room as a guest, surrounded by architects of all creeds and rank in this large corporation; bagels were ate, coffee was imbibed, hands were shook. This was my first glimpse into the architectural culture of my new employer. 

What took place was a long presentation on the values of storytelling for technologists, architects, and leaders; it was well made, and I won't go into any criticisms I have here. It was a long day, interspersed with role-playing elements which piqued my interest, as I had just recently made my foray into the world of Dungeons and Dragons. What I gleaned from this course was a mix of personal agreement, some obvious missteps, but most importantly (and perhaps a testament to the presenter) I started to reflect on story-telling.

Technical people are usually introverted
— Recent course at a major company

This was the paramount part of the course introduction, and I relatively believe this to be true. Most often the stigma of the introverted technologist holds up, but I began thinking about the years of gaming I've done, and my own beginner foray into fantasy role playing and storytelling. More importantly I began to think about how many introverts I've gamed with in the past; whether it was Everquest in college or more recently online role-playing, a correlation rang true: introverts as gamers are escapists, escapism requires a story, and games are technical.


Leadership and Architecture

I've touched on the every-changing definition of the profession of architect before, but what is always true, is that an architect should be a leader. Early on in my career I looked up to architects as all-knowing sages, and as a practicing architect I am looked at for decisions and leadership in the majority of my meetings, discussions, or governance. To be a storyteller, is to be a leader. Andy Raskin's article at is a great summation of why great storytellers make great leaders. Andy helps craft stories for leaders, most of his clients are venture capitalists such as Andy Horowitz of Google Ventures.

Very literally, leadership is storytelling and leaders are storytellers
— Andy Raskin, Advisor to CEOs and VCs

Storytelling however isn't a new concept, every culture and every person has experienced a story in their life; told, read, or seen. One great storytelling device I've recently found has been Dungeons & Dragons. There has been a recent resurgence of this board-game in popular culture; this New Yorker article from 2017 sums it up nicely. Being a nerd is cool in the 21st century, and there aren't many nerdier things than Dungeons & Dragons. Some of the resurgence can be attributed to:

  • Popular actors and actresses such as Stephen Colbert, Drew Barrymore, and Vin Diesel have attested to playing D&D on a regular basis. 
  • The popularity of The Big Bang Theory, where the characters regularly play D&D. The Big Bang Theory had at one point, over 20 million weekly viewers in the United States.
  • The web series Critical Role, which is played by several professional voice-actors, reached 140,000 concurrent viewers on their 2nd campaign debut in 2018. Critical Role has over 20 million Youtube views.
  • The popularity of the show Stranger Things on Netflix, where season one featured the protagonists playing Dungeons and Dragons.

It's clear that there are many prevailing reasons why a tabletop game created nearly four decades ago is making a comeback, and can be further summarized below:

Last year, Dan Harmon, the creator of “Community” and an avid D. & D. player, produced and starred in “HarmonQuest,” a role-playing television show with celebrity guests. He offered his theory of the game’s popularity: we have always been geeks, but we didn’t know how to break it to each other. Being a nerd is “not about IQ or different characteristics, it’s all about obsession and focus and taking something seriously,” he told Entertainment Weekly. “The internet really allowed everyone to realize that everyone was a nerd.” - The Uncanny Resurrection of Dungeons & Dragons, New Yorker


Unfamiliar inspiration

"Well, great and all, but how does a board game help me become a better leader and storyteller?" you might be asking. Let me sum up what happens in a typical session. First off, most D&D is done in person, where a group of players gather around the table usually with snacks and await the Dungeon Master / Game Master. The role of the DM, aka. Dungeon Master, is to tell the story and play referee to the players through a huge set of documented rules. We have our storyteller! But wait, there's more; the players are role-playing, and are tasked with telling their own story as well. The whole point of this is role-playing, allowing the players to escape to a new imaginative land through storytelling, both on their own and through the DM. Some players, such as Critical Role take this to the next level through professional voice acting, and some focus on the narrative. But one thing is sure, Dungeons and Dragons is all about story-telling.


A new GAME Master

Around the end of 2017, I decided with a group of people I normally just video game with, to embark on 'the experiment'. The experiment, being Dungeons and Dragons; none of us have ever played. I had a basic understanding through a nerdy collection of D&D books and some great video games like Baldurs Gate; but we needed a DM. I volunteered for this role. My first task was to pick an adventure, and fortunately the publishers of D&D have this readily available. The next task was choosing a way to do this, we chose our familiar voice chat and a couple online tabletop platforms: and


One of my characters, a salty pirate Tortle Warlock

One of my characters, a salty pirate Tortle Warlock

I began my role as a Dungeon Master. I chose a pre-arranged adventure "Tales from the Yawning Portal" as opposed to "homebrew", essentially an entirely original story written by the DM. I introduced my players to their world, provided hooks for the adventure, and on they went. I attempted voices for the characters and monsters they engaged, and over time I feel I became a better story teller. Where this differed from a book or a movie however, is that the players can attempt to say and do ANYTHING. More often that not, I was put on the spot, and story-telling took on a very impromptu creativity. I won't go into too many details, but at one point the adventurers decided they REALLY wanted in a door I had informed them was locked. Eventually a narrative evolved as after many attempts to knock down this door, they were met with a burly figure that was clearly not in the mood as he had some intimate company, eventually the story transpired and they were sent away laughing and mentally scarred.


An Introvert Becomes a Story-teller

I also started to play D&D with another fellow player where he is DMing (Dungeon-Mastering), a med-student, somewhat introverted and keen for escapism after long days shadowing doctors. He claims D&D to be the first creative thing he's ever done! I've actually witnessed an introvert become a story-teller!

So what can a bunch of introverts learn, how can they be better storytellers in their professional lives and become better leaders?


A Curation of Storytelling Tips

Below are a collection of storytelling tips I've researched to become a better storyteller:


Matthew Robinson and Ricky Gervais

Matthew Robinson and Ricky Gervais

Fast Company, 4 Lessons In Storytelling From a Screenwriter Who’s Also a D&D Dungeon Master

An interview with a professional screenwriter and avid new convert to Dungeons and Dragons, Matthew Robinson.

Don't Be Boring

Dreaming up scenarios and envisioning outcomes is a helpful skill in the world of D&D–and any time you have an audience, really. But those scenarios better keep people’s attention.

Storytellers are Puppetmasters

Controlling the pace of a D&D game means manipulating how and when details are revealed. Sometimes your audience wants to be deceived, even if they don’t know it.

Anticipate Audience Reaction

With D&D, you’re playing a game, but the game is really just a means to create the best possible experience for your audience. In order to do that, you have to know who your audience is and use that information to play off their expectations.

Turn The Script on It's Head and Improvise

Remaining rigid to your original vision is just as much a problem in writing as it is to D&D. Ideas evolve–sometime over ages and sometimes just after mulling it over for a bit, or starting a third draft. In either gameplay or writing, never feel beholden to the course you originally set out on.


Stephen King

Stephen King

The Storytelling King, a D&D Creator's take on On Writing and Danse Macabre

There aren't many storytellers more prolific and well-practiced in the world today than Stephen King.

Start with a 'what if'

The most interesting situations can usually be expressed as a What-if question: What if vampires invaded a small New England village? ('Salem's Lot) What if a policeman in a remote Nevada town went berserk and started killing everyone in sight? (Desperation) What if a cleaning woman suspected of a murder she got away with (her husband) fell under suspicion for a murder she did not commit (her employer)? (Dolores Claiborne)What if a young mother and her son became trapped in their stalled car by a rabid dog? (Cujo).

Never-mind the plot, engage the audience/players

I'm not able to guess with any accuracy how the damned thing is going to turn out, even with my inside knowledge of coming events, and . . . why worry about the ending anyway? Why be such a control freak? Sooner or later every story comes out somewhere.

Looks aren't everything

I can't remember many cases where I felt I had to describe what the people in a story of mine looked likeI'd rather let the reader supply the faces, the builds, and the clothing as well . . . Nor do I think physical description should be a shortcut to character.

Let dialogue define

It's dialogue that gives your cast their voices, and is crucial in defining their characters.

Learn by Osmosis

When I read Ray Bradbury as a kid, I wrote like Ray Bradburyeverything green and wondrous and seen through a lens smeared with the grease of nostalgia. When I read James M. Cain, everything I wrote came out clipped and stripped and hardboiled. When I read Lovecraft, my prose became luxurious and Byzantine. I wrote stories in my teenage years where all these styles merged, creating a kind of hilarious stew. This sort of stylistic blending is a necessary part of developing one's own style.

Let character, not event, steer the ship

The best stories always end up being about the people rather than the event, which is to say character-driven.

Put the party (audience) on a teeter-totter

All fantasy fiction is essentially about the concept of power; great fantasy fiction is about people who find it at great cost or lose it tragically; mediocre fantasy fiction is about people who have it and never lose it but simply wield it.



Want a Better Pitch? A Breakdown of Elon Musk's Pitch for Tesla Powerwall

Not quite D&D, but a pitch is a story. Andy Raskin's breakdown, an the first thing he sends to people looking for advice; how Elon Musk get's people excited for... a battery.


Name the Enemy

Never start a pitch by talking about yourself, your team, your product, or your total addressable market. Instead, start by naming the thing that’s getting in the way of your customer’s happiness. Do that by painting an emotionally resonant picture of how your customer is struggling, who/what is to blame, and why. When Musk shows this image of burning fossil fuels, you can practically hear Darth Vader’s ominous breath.

Answer “Why now?”

Audiences — particularly investors — are skeptical. They’re thinking, “People have lived this way for a long time — are they really going to change now?” Musk handles this objection by showing that we’re at a critical point in the growth of atmospheric carbon dioxide concentration: If we don’t act now, things quickly get much, much worse. When Musk says, “We should collectively do something about this,” his audience howls in support.

Show the promised land before explaining how you’ll get there

Before saying anything about batteries, Musk describes his version of happily-ever-after: a civilization powered by “this handy fusion reactor in the sky, called the Sun.” Showing the enemy’s defeat before explaining how you’ll make it happen can feel wrong for novice presenters — like blurting out the punchline before you’ve told a joke. But when an audience knows where you’re headed, they’re much more likely to buckle in for the ride.

Identify obstacles—then explain how you’ll overcome them

Now that you’ve shared your vision of the future, (a) lay out the obstacles to achieving it and (b) show how your company/product/service will overcome each one. (There had better be some big, nasty obstacles — otherwise who needs what you’re selling?)

Present evidence that you’re not just blowing hot air

Again: audiences are skeptical. So you must give them evidence that the future you’ve laid out is, indeed, attainable. Musk does that by letting his audience in on a secret: Powerwall batteries have been supplying the energy for the auditorium in which he’s speaking. As proof, he zooms in on the meter above, which registers zero power from the grid.

Low Risk, High Reward

So this is all well and good. However, Dungeons and Dragons has leeway, there are no real world consequences to a badly told story in D&D; there are however consequences and hopefully good results in how an architect or IT leader tells a story. There is a guiding star for architects and IT professionals; these are quite literally guiding stars in a cultural sense, people like the late Steve Jobs or the current Elon Musk. Technologists that are making huge impacts on the world today HAVE to be storytellers, and we all have to start somewhere. Why not start with a game?

The great storytellers have an unfair competitive advantage. They are going to recruit better, they will be darlings in the press, they are going to raise money more easily and at higher prices, they are going to close amazing business developer partnerships, and they are going to have a strong and cohesive corporate culture. Perhaps more to the point, they are more likely to deliver a positive investment return.
— Bill Gurley, Benchmark (A big VC Firm)
Jesse Myer