So I’ve made no secret of the fact that over the past two years I’ve gotten back into Dungeons and Dragons and role-playing games in general. And to be honest for my core group, this COVID-19 situation made our group a lot tighter and since March we have now been playing weekly.

Now I will say, that I’ve talked about the benefits of TTRPG (table top role playing games) during COVID-19, that it’s a great way to step out and have fun with people in a way that doesn’t feel forced. But I’ve also noticed that I’ve learned a lot by running these games that I take as life lessons. And I definitely recommend this hobby as a way to grow and have some fun.

Let’s start with the connection here, in a TTRPG, like Dungeons and Dragons, you and a group of others are building a story. The game is about you all building the best story you can, and along the way dealing with outcomes that are decided by a mixture of planning and chance.

Let’s talk high level, just to make sure we’re all on the same page, for example, if you know your characters going to be doing lots of sneaky things, you might take a stealth skill, which gives you a +5 to stealth. So now when you are presented with a situation like that in the story, and the Dungeon Master says “give me a stealth check”, you roll a 20-sided die, and add the +5 to it. Now when you built your character you had to make choices, so using the above, I might have spend points to make myself stealthy, but odds are I’m not intimidating, so an “Intimidation check” might be a 20 sided die, and a -2, much lower chances of success.

To this end if you want to get technical about it, a Dungeons and Dragon’s campaign is a lot like a project, we have a goal, and we have a team of people all bringing unique talents to the project. And we have a dungeon master that is there to help us organize around a goal and work towards it. This should sound a lot like a work project, at least this is the similarity that really struck me.

So I’ve learned a lot being a dungeon master that I feel has direct parallels to my chosen careers and leadership, and I wanted to share those here.

But here are the top seven things I learned by playing these games:

Lesson 1 – What true collaboration looks like?

Ultimately, at the end of the day, when you play a game like Dungeons and Dragons, the game is communal story telling. We are all collectively telling a story. That means that although I control the settings, the non-player-characters, and monsters, the players are just as much in control of the story as I am. In this game, they are the protagonists of the story.

So if we consider this as a collaborative effort, its not unlike your teams at work, your manager is responsible for setting the guidelines, defining the goals and supporting the team (much like the Dungeon Master). The players are responsible for tackling the challenges that are thrown their way and moving towards those goals. Again not that different from your office if you think about it. Sure you’re delivering a product, report, a software solution, and they are fighting goblins, but overall the principles are the same.

So one of the things I learned here was what it means to be in that position and truly collaborate. Because as a Dungeon Master (DM), it was my job to make sure that everyone contributed to that story. And what I learned quickly is that to do that you need to truly collaborate, and make sure that you are giving space for others ideas. One example of this, is that I had very much an idea of the direction that I wanted to take things, but I had to be open to anything. So one of the things I decided early on was to “Find a way to say yes.”

And this did a couple of things, that really embraced creativity and collaboration:

1. My team mates really felt invested: Nothing makes you more invested in the outcome than to know that you’re ideas are being heard and appreciated.
2. They came up with ideas that I never thought possible: Some of the things they came up with were really awesome, and I never would have. And that made the story better, or made it possible for us to do more than I thought we could.
3. It Challenged me in a new ways: By forcing myself to find ways to enable their ideas, it presented me with new challenges I never thought possible before.

Lesson 2 – What it means to empower and say yes?

Now just like managers, there are lots of different types of dungeon masters out there. Some see their role as being against the players, others see it as their story that they need to force the players to follow, and I’m betting you’ve had managers who work the same way.

I don’t know about you, but I’ve had managers that believe they have to be better than anyone who works for them, and feel threatened by their success. I’ve had other managers that felt that “I’m the leader, and make all decisions for every aspect of this project.” And too be honest those were terrible experiences, and I’ll be honest early in my career I could be accused of being one of these, and it wouldn’t have been far off.

But I’ve been lucky to have a lot of really good managers in my career too, and one in particular always said “It’s my job to see you successful.” And that was always inspiring to me. So when we started this dungeons and dragons game 2 years ago. I decided that I was going to be a “Try to say yes” leader. And what that meant was a very simple rule.

Anything reasonable the players wanted to do, before I could say no, I had to do everything in my power to say yes.

Now just like the real world there are limits. If a person on your work team said, “I want to make $1M a week.” That’s not reasonable, and I saw this as an impossible situation to make a “Best Effort” to say yes.

But I decided when my players decided to roll characters, I would find a way to say yes. So when a player came up with a character concept, I would try to find a way to make it work.

For example, I had a player who had a very long backstory they wanted to do with a illustrious history, and normally any online advice on the game would say “Never allow this for level 1”, but we figured out a way to explain how they had gotten older and fallen in levels. And to be honest, I found the challenge of trying to find a way to say yes, really fun and empowering myself.

This also meant as a leader that my team members saw me fight for their success. They saw me trying really hard to make their ideas reality, and this made them invested in the project.

If you are an employee and every you go to your manager with a new idea, they tell you “That won’t work.” Are you really committed to delivering on that project? Are you committed to helping that person? Probably not.

But if you go to your manager with a new idea and here, “That might be tough, but let’s talk it through? Or let me see what I can find out?” Are you going to do more to help? Do you feel more invested in the outcome? Probably yes.

Lesson 3 – People communicate differently

Another key lesson I learned was specifically around communication. Right now my core dungeons and dragons group is 7 players, plus myself as dungeon master. And over the past two years, we played monthly for about a year and a half, and then played weekly since COVID-19 hit in the US.

Our group is pretty eclectic, and we have made some really strong friendships over that time. And I’ve learned a lot about communication and experience with regard to everyone. Some people communicate differently. And as a dungeon master, I’ve had to learn to communicate in the ways that make them feel most comfortable.

For example, I have one friend who will randomly message me on discord (our chosen app) during the week to ask random rules questions, or talk about ideas he has revolving around his character.

My wife, who has become a big fan of the game. Prefers to talk at night before we go to bed, and brainstorm ideas about our character and discuss events in the game face-to-face.

I have another player, who I have to reach out to them as it is harder for them to ask for help or express their opinion during the game.

And I have a third, who would rather ping me to ask if things would work before they do them because they are afraid of looking like they don’t know the answer.

Now reading that list above, I’m sure if you’re like me you can think of at least one person in your work and that statement lines up perfectly. The simple fact is that communication preferences aren’t unique to a game, they are likely the same for all parts of that person’s life. If people don’t have a lot of confidence they are more likely to stay quiet in a meeting. And “cold-calling” that person, likely isn’t going to do them any favors.

So being a dungeon master, I’ve had to learn that my preferred communication style matters, but I have to be empathetic to how others communicate if I really want to get the benefits of collaboration for everyone. And to be a good leader, you should absolutely want to meet people where they are, and it’s been great practice that in this kind of setting.

Lesson 4 – How to make sure everyone is in the conversation.

Along with the need to focus on how others communicate, one thing I’ve learned playing Dungeons and Dragons, is how to make sure everyone is at the table.

Stop me if you’ve heard this one before:

You all get together for your regular meeting for a working session on the project and as the meeting progresses, you are all moving things forward, and things seem to be going well. But you’ve noticed the past few meetings that one of the members of team has been quiet, and isn’t contributing much to the project. You really like this person, they are a fantastic resource, so you assume their silence means they agree with everything being said. At the end of the project, you discover you are missing key requirements in this person’s area of expertise, and the project is in trouble due to these missing pieces. The manager of the project is frustrated and feels like your friend didn’t do their job and wants to fire them.

When you approach the person, they confide in you, that they were afraid that no one would accept their ideas, and although things went different than they thought they should. They didn’t feel comfortable speaking up.

Sounds like a work scenario that we can all relate to right? I’ve seen this same thing happen at the gaming table. And one of the most valuable leadership lessons I’ve learned is how to identify situations where someone is not contributing because of a blocker, and how to navigate that. Looking at the above, most would say “All that could have been avoided by stopping and calling that person out to offer an opinion.” But for some people that is a terrifying version of hell.

Another way to address that would be to become an ally for that person. Like I had this situation with a player, and I reached out to them, 1-on-1, and had a conversation. “What do you think about what happened?” and “Let me get your thoughts?” And then our next game, I started with “______ and I were talking, and they had some really great thoughts about this…” In this way, I’m helping them to feel like someone in the room is validating their ideas and giving strength to them. Which is a key to leadership.

Lesson 5 – People are motivated and enjoy different parts of the project.

This was something that I found very helpful. When you have a group playing a game like this, they are all measured by different things. For me, first hand I saw the following:

• Some people love to play out combat in the game, and to them every thing with story is only there to provide more opportunities for combat.
• Some people love the story and roleplay moments, and are interested in character arcs and live for roleplay moments.
• Some people are there for the whole process of building and optimizing their characters.
• Some people are just there to be part of a team.

So as the leader you need to make sure that you are aligning activities and opportunities with people who want them. Like for example, if I have a player who lives for combat, a great roleplay situation is going to fall flat for them, and be a missed opportunity for the roleplayer.

It’s not a stretch to see how this impacts your ability to lead a team in a professional setting. Some people are there to punch a time clock, others enjoy coordinating and running meetings, while others want to just roll up their sleeves and code. And to get the best out of the members of your team, you should make sure that people are given the opportunities to engage in the types of work they enjoy and excel at.

Now as we talked about before, just like communication styles, it isn’t always obvious want people want or what drives them. But its really important to take the time to do that. By doing so, you accomplish the following:

• Further show the members of the team, that you care about them, and how to maximize their contribution to the team.
• Allow opportunities for people to stand out for their accomplishments, and to be the hero.
• Provide new opportunities for people to try things without fear of failure. By allowing them to take risks you empower them to do more as members of your team.

Lesson 6 – It’s not my success to own.

This is one, where a lot of Dungeon Masters get it wrong. But as part of playing these games, and being the leader. It’s my job to create the challenges and things they have to deal with on the journey. And during those times, the players have to rise to the problem and defeat the monster, break into the citadel, etc.

And in the course of running these games for the past 2 years, I’ve seen things go a wide variety of different directions. And a lot of times, they go directions I never thought possible. And the biggest ones I’ve seen success for, are things like this:

I had a situation where I built a game for my players, and had planned this long combat encounter, and it was going to be intense, and I didn’t know if the players would survive. And when we ran the game, my players took a bunch of different directions I’d never thought of, and the multi-session encounter I had planned was over in 1 hour. The players were thrilled, and ecstatic. They had rose to the challenge and overcome it in an interesting way.

And to be honest, if you search for these types of situations on forums or blogs, they will talk about how much this sucks as a Dungeon Master. They will point to all the work you did and how they “beat me.” I have to be honest, I couldn’t have been more proud of my players. They did great, and the success was theirs. The team had accomplished something great, and honestly it was their success. Had I helped enable this? Absolutely I had helped them build and grow as players to the point that this was possible. And honestly, it made me feel proud and accomplished, but nothing about this game is my success it’s ours.

And honestly if you look back, I think you will find that the best leaders in your career had one thing in common, they took their ego out of it. You can’t be a good leader in your career and allow your ego into the equation. You need to be proud of the work you do with others, and you need to be proud of their accomplishments.

And here’s something I’ve learned from one of the best bosses I’ve ever had…”The best leaders take the team out to celebrate, and pick up the tab.” And the way I view this ultimately, is that the best leaders are the ones who even empower and facilitate the celebration of their team. They don’t say “Look what I did with my team!”, they say “Look what my team did!”.

Lesson 7 – How to draw the lines on the field, not control the game.

We’ve all had majors in our careers that have tried to control everything. They must approve every detail of a design, they must review every line of code, and they must be involved in every aspect of the project so that they can “Control” the outcome.

I’ve always known that the best managers don’t do that, they draw the lines on the field, they set the value and direction, but they let their team play the game. And there are a million sports metaphors about this. But I found that TTRPG, give a real quick lesson in this, because during the game I have no control over my players, I setup the scenarios, I adjudicate the rules, but I have no ability to control what they do, or how they react to situations. And it creates a situation where I get to see the success of my team and am always put in a position where I have to accept this fact.

In other situations in my life, regardless of how much I knew this to be true, the nature of TTRPGs, requires you as the dungeon master to only engage in this way, as I don’t have a player in the game, and I can’t control their actions, and it was a great learning experience.

Learning comes from strange places…

So honestly, this is something I wanted to write about, because over the COVID-19 crisis, I’ve found that I learn a lot of new things from a variety of places. And overall I’m trying to make myself more open to these. But I was surprised by the amount of team and leadership learnings I got by putting together a game where people kill dragons.