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OD&D&D [Organizational Development & Dungeons & Dragons]


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In my experience, D&D [Dungeons & Dragons] and similarly complex games relate to - and can teach us about - the field of OD [Organizational Development]. If you have ever seen me present, this notion is probably not new to you. Be it playing games with friends or implementing organizational changes, you are engaging in highly complex systems affecting different people filling different roles. This inevitably results in a lot of challenges that must be overcome as a group. So, the next time you're stuck with how to proceed in your OD objectives, why not try breaking out the dice and miniatures?!

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Understanding the game & opting-in

Whether we are talking about your favorite games, your professional career, or a community volunteer program you just joined, you need to understand what you are doing and how it works. In all aspects of life, whether fun or necessity, not having clarity of how things work creates stress, anxiety, and makes things less likely to be accomplished.

When my wife and I started to explore Dungeons & Dragons as a potential hobby, our first experience was a terrible one. We had played a video game for years where "stealth" mind becoming completely invisible. You could dance around your enemies and they would have no idea you were there.

It doesn't work that way in D&D, but we didn't know. So, a few minutes into our very first game, my wife wanted her character to "stealth" and run straight at the enemy. The GM (Game Master, i.e., the one who runs the game) laughed at her and had the enemies attack her, as they clearly saw her. In addition to feeling shamed, we were also perplexed. We had known what "stealth" meant for years and suddenly it meant something else.

This same thing happens in organizational development all the time. I have seen hundreds of people be simultaneously bewildered by changes in words they had known their whole life that now meant something different because of the new rules being implemented. For example, you might think "Policy" means a rule you have to follow, no questions. That is, unless your company is implementing Holacracy, at which point "Policy" means something "which are either grants of authority that allow others to control or cause a material impact within a Domain, or limits on how others may do so when otherwise authorized."

That is just one example of just one method of just one type of organizational change. This is the very first of many challenges when implementing changes in an organization: making sure people comprehend the language the game is played in. Is there a new lingo? Do things operate differently now than they did before? You can't learn a new system unless you understand what things mean.

Knowing the bigger context & purpose

One of the first steps in starting any new game is understanding the context of the world in which you will be playing. I might want to play an adorable little character with fun, pretty magic in a world that reminds me of Alice in Wonderland where all I want to do is explore and uncover the story. If the game starts and I discover we are in a haunted wasteland of monsters and we will be fighting life-or-death battles constantly, I as a player would be mortified. I likely wouldn't have fun and would spend every game wishing I had played a character more appropriate to the setting.

The same thing happens in companies every day. If I work at a company full of young jokesters as we build a video game app, I am probably going to conduct myself very differently than if I am surrounded by buttoned-up, serious individuals as we handle sensitive, million dollar contracts. Even if I know how people act and what we do, I might yet still approach it differently based on why we do what we do, such as having a bigger purpose. Is our game app just to be fun and make money, or is it an educational game and the profits go to those in need? That context alone will drastically alter how I perceive and approach my work.

Before you start, players and workers alike need to understand what is about to happen and why. They need to see the bigger picture, be aligned with how we will get there, and understand the point of it all. You also need to understand that every individual has a different reason to want to be there which should be catered to as well.

Gathering the right team & psychological safety

While my first game of D&D wasn't great, a handful of other games to follow all had their share of problems. With each game, we learned what we did and didn't like and would mention that when started following games. Still, finding a new Game Master was risky. We used to take whatever we could find, then sometimes regret our decision later. At that point, we would have to decide whether it was tolerable enough to keep going, or make the uncomfortable call of quitting, making someone feel bad, and being unable to play. It was unpleasant all around.

Sadly, this is how many organizations operate, and even those with the best of intentions fall victim to it now and again. Sometimes, a person is simply hired without a second thought because a role needs filled or they are a friend of a friend. Other times, due diligence is done, but things change, you couldn't predict what might happen, or you didn't consider verifying the specific things that might have prevented a falling out. A once wonderful working relationship has turned into a group that can't work together and something uncomfortable has to happen.

Now, when looking for someone to run our games, I post a multiple page document thoroughly detailing our playstyles and preferences. It covers what we do and don't like in games and settings, tweaks and changes to the game we enjoy, and preferences for character options. It also covers a lot more personal stuff, such as what we need to feel comfortable, what types of people we refuse to interact with, our boundaries, and more. It ends with asking people to reach out if they think themselves a good fit.

It works beautifully and results in a perfect fit nearly every time. They know what to expect of us as players and we know what to expect of them as the one running the game. Of course, we also ask and respect their own needs, but they already knew that because we call that out too.

Thankfully, this is also what more and more companies are doing every day. By being upfront about the good and bad, it does just as much for the company as it does for potential employees. I have seen what looked like great jobs, but I knew I wouldn't resonate with the values or the mission of the company, so I saved us both time and didn't apply.

Additionally, any company is theoretically capable of learning from mistakes and using that to improve hiring and onboarding processes. Every worker who doesn't work out can be seen as an opportunity to set future prospects up for success more effectively.

Conflict Resolution

Conflict is inevitable. As mentioned above, there are ways to prevent the need for it as often, but conflict is bound to arise. Whether it's at work, home, or traversing a distant fantasy realm online, misunderstandings and arguments might pop up at some point. You need to know what to do in those situations, as trying to figure it out in the spot won't help anyone.

In Dungeons & Dragons, like in most organizations worldwide, it is clear who technically has the final say. Whether it's the GM or the CEO, the rules say that one person likely can make whatever decision they want and everyone else just has to deal with it.

Luckily, leadership comes in all forms. While any GM could say, "This is my ruling. Deal with it.", most wouldn't. That would make the game unpleasant, wouldn't take players' opinions into account, and would make the game feel more like "us vs them". The good GMs will explain their opinion, allow room for questions and debate, and work on coming up with a solution that benefits everyone while keeping the story going.

The same is true of leaders in the workplace. Often, anyone with a "leadership" title in the hierarchy has some degree of absolute power over those beneath them. Can they squash ideas and force their own agenda? Sure. The great leaders, however, don't do that. They seek to listen and understand. The mediate and facilitate conversations. A final call will be made only if no other middle-ground can be reached.

Some companies address this proactively with an explicit conflict resolution process - a set of rules that clearly details how conflicts will be dealt with. These systems are typically tried and tested to give ample room for discourse, varied opinions, and clever solutions to whatever problem is presented. Having such a system means that when a conflict arises, all parties know how to address it in the most effective way.

Remote Work

Throughout 2020, countless individuals were introduced to remote working for the very first time. For many, it was stressful and confusing. It required getting more hands-on with technology and software they had never used before, let alone having to juggle multiple apps simultaneously.

Thanks to years of playing MMORPGs, none of this was new to me. I had already been well accustomed to joining guilds and communities of people I knew only as online avatars. Every week, we raided the lairs of giant foes together in groups of anywhere from 10-40 people. Gameplay aside, it was no easy feat. The bigger challenge was the logistics.

It required finding a time slot and duration which fit the schedule of everyone participating, even across multiple time zones. Everyone had different jobs, school hours, family responsibilities, and preferred times of playing. It also meant finding the best software for us to be able to speak to one another, despite everyone having different computer setups and thus needing something compatible for every device.

When I first started to play TTRPGs, it was all in-person. Then, after moving and experiencing a pandemic, everything transitioned to being online. You have to find how to locate people wanting to play the same game as you, how to chat with them, what site to use to show maps, what tool to roll dice. It was a lot, but for me, it was nothing new.

Hence my confusion when I saw countless business owners being bewildered as to how to transition to remote work, even if just for meetings. Granted, I never had to figure out the technical difficulties of moving coding infrastructure to a secure, cloud-based system, but these were also a drop in the bucket of complaints I saw. Most of them were how to maintain team relationships, how to ensure work was getting done, and how to have effective meetings.

These concepts were, to me, nothing new or difficult. I had spent years building relationships, creating accountability, and accomplishing group projects all with a variety of different online tools and software. A handful of the tools I had relied on just to play games with friends were now being utilized by entire corporations across the globe. While I felt no new transition through it all, I understood what it felt like when it was new to me and allowed me to empathize with the complexity of balancing the numerous options out there.

Simplifying the complex

Dungeons & Dragons, like many games, is incredibly complex at first glance. If you want to play and understand the game in its entirety without someone else teaching you how to do it, you'll need to read and comprehend multiple books, each hundreds of pages long. There are more books of creatures, more books of adventures, and more books of potential different rules if you want to mix it up. For a beginner, it can be absolutely overwhelming.

The same is true of many organizational development initiatives. Some premade structures have lengthy rule sets detailing how everyone will now work in this new environment. You'll have to learn and understand a new set of rules, a new language, and all new processes for going about your day-to-day. Even changes without an explicit set of rules can have so many differences that working becomes hard alongside all the learning you have to do just to understand what is going on.

As with all things, setting realistic expectations and giving helpful introductions to new concepts can completely change how even the most complex changes will be perceived.

For example, I could tell you that attacking requires rolling a d20 plus your attack modifier plus your proficiency bonus compared to the enemy's armor class. You could look all of that up in the appropriate rule sets and piece it together yourself eventually. Or, I could say, "Roll this dice", then tell you whether or not you hit. You may not understand how it happened at first, but the fun will start immediately and you can learn the nuances as we go.

The same is true for organizational change. Rather than telling you all the changes, all the possibilities, and all the new interactions right off the bat, there's probably an easier way that lets you work without being completely burnt out by new information.

By only teaching what is fundamentally necessary at the start, while using easy-to-understand language and metaphors, and implementing bit-by-bit in a sustainable way, you can take any daunting, confusing change and make it easily accepted and applied.


This is normally where the conclusion would be.

Replacing tradition with efficiency is kind of our thing.

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