Why should OD&D Practitioners (and anyone interested in leadership) play D&D?

Mark Buttanshaw
11 min readNov 6, 2023

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Three pumpkins from a table display. The largest pumpkin has been carved as a jack-o’-lantern with the letters ‘OD’ carved out instead of a typical jack-o’-lantern face.
An OD[&D] pumpkin from Roffey Park’s OD conference

In my previous blog, I was so inspired by Roffey Park’s OD conference that I owned up to my social identity as a geek who plays Dungeons & Dragons [D&D]. It doesn’t sound like it would crossover with my perception of Organisation Design & Development [OD&D] which seems to be concerned with much more ‘real’ things about people and organisations. And why would I spend my spare time playing D&D when I could be using it for reading some new book about leadership / culture / people (etc.) or journaling to help me explore and understand myself better?

I hope I successfully showed in that blog that D&D has some important concepts for organisations. The ideas might not be groundbreakingly new, but I think D&D provides some powerful examples of generative conversations. Organisations could learn a lot from the conditions that D&D groups create sat around a table as equal participants and creating a shared story. I think it would be transformative for more people to have this kind of mindset when at work, not just when ‘playing a game’.

And if you haven’t read my previous blog, I suggest you start there because this builds on some of those ideas (with some of the explanations about how D&D works if you’re new to it). I’m aiming in both my blogs to learn through playfully linking OD&D with D&D, and I’d love to hear your thoughts!

I use the terms ‘OD&D practitioners’ and ‘leaders’ for this blog because I think that people with positional responsibilities need to own the impact we have in different situations and own how we show up (e.g. not taking out something going wrong on someone else). More generally, I also subscribe to a distributed view of leadership, that we are all leaders in lots of situations whatever our formal position in an organisation is, so hopefully this blog explores leading regardless of your formal role.

But seriously, why should we play D&D?

D&D is first and foremost a game. It’s about having fun and creating shared experiences with your friends, or people who will go on to become your friends if you continue meeting up with them. To play it to have fun is a good enough reason to stop reading right now — we all need fun in life!

For those not convinced that playing it for fun is enough of a reason, I have a few other thoughts… Yes, D&D is a roleplaying game set in a fantasy world, and… I think D&D has a lot of ‘real world’ implications. The whole structure of the game is about the choices you make and actions you take in a range of scenarios. These actions and choices have consequences within the game which the Game Master [GM] will incorporate into what happens in the shared story you’re creating. This can give you an opportunity to see from perspectives which aren’t your own, learn about yourself and try things out in a safe environment (and I expect you could say the same about other roleplaying games, but I know D&D the best).

I think there are three core reasons we should all be playing Dungeons & Dragons:

1. D&D allows you to experiment and offers real-world insight.

2. D&D encourages talking about boundaries and creating a healthy environment.

3. D&D recognises how character grows and changes over time.

D&D allows you to experiment and it offers real-world insight

One of the great things about D&D is how much you can customise your character. As well as deciding on your character’s species (human, dwarf, elf etc.) and class (fighter, wizard, cleric etc.) which I mentioned in the last post, you also make lots of other decisions to develop your character. Some are linked to mechanics of the game… for example you get to choose stats about how intelligent, wise and strong your character is (and more). Other decisions are about getting ‘in character’ and working out how you’re going to roleplay them. The heart of this is your character’s ‘backstory’ — what was your character doing before they became the adventurer that you are roleplaying now? Maybe they were a humble farmer or a sailor, or maybe came from a rich family. Who were the important people in their life? Why are they becoming an adventurer? Have they always travelled and encountered different species or did they live in a smaller version of the world in their cosy hobbit hole? And linked with these experiences, what are some of their character traits and flaws?

Bilbo deciding he does want to go on an adventure and will leave behind his cosy and safe life after all in ‘The Hobbit’ film.

The backstory for your character affects how that character might respond to different choices or barriers they face. This creates opportunities for an individual player to experiment with different perspectives. How do the cumulative experiences of a character influence their choices now? What unites them with the other characters in the party? Are they motivated for the adventure because they’re being paid or because they have a point to prove, or a grudge to settle? And would they run away when things get tough and their friends are in danger? If a character just wants a simple life or to be comfortable, facing the dangers of adventure (which can even include in-game death of a character) is not likely to be for them. So the motivations and choices of a character matters to the outcome of the game.

When we think about a character’s backstory we can be prompted to think about our own ‘backstory’ too: what are the things in life that have led to us being who we are here and now? Who were the important people in our life? What has motivated us to get to where we are right now in life? Would our world view change if we started out poorer or richer or lived in a different country? What does it feel like to have our eyes opened to a bigger and more diverse world than we realised existed?

A D&D game is a safe way to experiment with taking different perspectives and having different experiences. We can experiment with how it feels to hold social identities which are different to our own. We can try out different ways of responding to situations and learn about ourselves as we do. Of course, we can’t assume that through roleplaying we actually know what other people’s experiences are like, particularly of what it’s like to be marginalised and excluded. But we can increase our capacity to empathise and try and see things from alternative perspectives to our own. In the right setting, D&D can provide space for exploring grey areas and can push your personal philosophies through the power of imagination and how actions have consequences. Do the ends justify the means? What if you sell your soul in the course of defeating the evil tyrant and end up becoming one yourself?

In OD&D terms, this corresponds to the concept of ‘use of self’ because the roleplaying in D&D can give us an opportunity to try out different things in a safe space with friends. This opportunity to experiment in the fantasy setting of D&D can in turn help us to learn more about ourselves in the ‘real world’ and have a more grounded sense of self. For all leaders, the ability to reflect on yourself and how you show up is critical. By better understanding ourselves and our motivations we can be authentic and intentional about what we do, and work in a way which builds confidence in others.

D&D encourages talking about boundaries and creating a healthy environment.

A D&D game can be many things to many people, and the preferences of different groups will create different dynamics. Some people prefer a ‘hack-and-slash’ adventure which is mainly focused on fighting monsters and using the different fighting skills each character has, while other groups may be more interested in an adventure around political intrigue and roleplaying. D&D is a flexible gameplaying system which can accommodate many different preferences. The key to any D&D group’s success is that everyone at the table needs to buy into the overall approach and feel safe. This isn’t forcing everyone at the table to have the same views; it’s having mutual respect of each other’s preferences and perspectives and seeking to create a healthy environment for the group to thrive. Without common boundaries and expectations which are made visible, D&D groups won’t stand the test of time (and nor will organisations).

As mentioned above, roleplaying in D&D can lead to new insights about yourself as a person — and the cast of Critical Role often half-jokingly refer to D&D as offering therapy. A home game of D&D is by no means a replacement for professional therapy and it shouldn’t be treated as such. But in a safe and trusting space it can be possible to experiment and explore things about yourself. Particularly when a D&D game might touch on things which could be difficult for people, it’s essential to have conversations which create safe boundaries.

A core concept that the D&D community have developed for talking about boundaries and creating a healthy environment is a ‘Session Zero’. The Game Master [GM] runs this for the whole group before the main story starts to talk about boundaries and expectations in the campaign. The GM might also have 1:1 conversations with individual players if it’s helpful. This session zero is a helpful way of creating boundaries to make sure that all the players and the GM feel safe. This might involve the GM having some extra/different game rules to standard and also might be setting boundaries such as whether players are comfortable for their character to be in a romantic relationship within the game. Because D&D can be so open-ended it’s important that these boundaries are discussed and respected by all the participants. However, simply having a session zero isn’t enough. It’s important that the players keep talking to each other outside the game as things come up, particularly if anyone seemed uncomfortable to make sure that boundaries are being fully respected. People’s boundaries also change so it’s important to keep reviewing how things are going on an ongoing basis.

For leaders and OD&D practitioners, D&D can be an opportunity to experiment and learn. If you’re the GM, running a session zero is the equivalent of having contracting conversations. You agree ground rules and talk about how you’re going to work together as the group and how you will keep checking in. As a player you interact with other people in the group, negotiating over what’s important to you and seeking to create a healthy environment which respects all the other players. Everyone around the table has a responsibility to the experience of the other people and needs to be sensitive to signs of people being uncomfortable to make sure that the game is fun for everyone. Those are lessons that D&D groups learn through experience in a safe way with friends who will usually be more forgiving when we mess up and more open to talking about what’s really going on than we might find in organisations. It’s not the only way to learn these things but the power of D&D and roleplaying creates unexpected situations that can prepare us for how we create the right boundaries and a healthy environment in organisations.

D&D recognises how character grows and develops over time

Part of what keeps people coming back to games of D&D is how the characters grow and develop over time. Within the game, that happens very literally through getting ‘experience points’ which correspond to growing a level (aka levelling up). When you level up, your character gets more powerful. This can be things such as becoming physically stronger or learning new spells. The fun of unlocking new abilities and trying out new skills or spells is an incentive to keep playing the game, and to try out other types of characters in future games.

Growth and development aren’t just about the game mechanics though as this can also be about your character’s personal character. Having written a backstory of your character’s past experiences, D&D games encourage you to explore elements of your backstory further — maybe to seek out someone important who went missing, or to seek reconciliation with someone. The decisions and actions you take are cumulative and shape the character going forwards, and GMs will incorporate character arc into the story. A character who started out trying to live for the benefit of others may become more self-seeking as they accumulate power and influence, or a character who had a bad start in life may be able to make different decisions and becomes a hero in the end. Roleplaying recognises that characters are imperfect and have character flaws, and sometimes character which develops under pressure can be positive and sometimes can be negative.

As leaders and OD&D practitioners, it’s important to recognise that as humans we are not static and we keep growing and changing. It’s a helpful and healthy part of being human and will naturally happen over time in people and organisations. We too can enjoy learning and practicing new skills, applying new approaches, theories and models to our work as we ‘level up’. And as an immersive roleplaying game, D&D also gives opportunities to test different paths and where they lead to so that we can learn from the experience. In the ‘real world’ our choices also add up in our character and we need to pay attention to the ethics and morals of the decisions we take. Do they take us in the direction we want to be going in?

The power of games and roleplaying

“I love OD&D so much, you can see it everywhere and nothing can’t be explored and learned from”. David Buck

The roleplaying and stories of D&D is a simplification of the whole human experience but can offer us insights which we can bring into the ‘real world’. It offers us an opportunity to experiment with different perspectives and personas, learning sometimes from things which go well and also from the things which don’t. It can help us learn from experiences of creating boundaries and healthy environments for people and groups to thrive. And it also recognises how character grows and develops over time and our decisions shape who we are.

I’m only starting to touch on some of these ideas briefly, and would love to continue the conversation if there are areas of the overlap between OD&D and D&D you’re interested in exploring more. I’m also generally a fan of board games and there can be lots in other games which make us think. A recent conversation with a colleague about how gamification could be used in OD&D to help leaders make better decisions also reminded me of the time when OneTeamGov played Powerplay. That was a game specifically to think about power (who has it and who doesn’t) which gave me a lot to think about how I use my own power and whose voices are being heard.

As with the improv games from Roffey Park’s OD conference which inspired this, I think there are lots of things that we can learn from playing games and especially from roleplaying games that can be applied in organisations. And as leaders and OD&D practitioners playing D&D, I think we’ll find that those experiences of creating a shared story around a table are actually just as ‘real’ as our day-to-day work.

So anyone for a game of D&D?

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Mark Buttanshaw

Curious about people, organisations, systems, leadership, culture and why things work or don't. Seeking to act justly, love mercy and walk humbly.