Career Development
Dungeons and Collaboration
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Dungeons and Collaboration

Rolen Le • November 08, 2022 • Denver, CO

The video titled "Dungeons and Collaboration" by Rolen Le, presented at RubyConf 2021, draws parallels between the game Dungeons and Dragons (D&D) and collaborative work in software development, especially among distributed teams. The talk explores lessons learned from years of playing tabletop role-playing games (RPGs) and how these experiences can enhance teamwork and communication in a professional setting.

Key points discussed in the video include:
- Understanding Tabletop RPGs: Rolen describes what tabletop role-playing games are, emphasizing that they are forms of collaborative storytelling governed by rules, with players taking on roles in a shared narrative facilitated by a game master (GM).
- Finding the Right Game and Group: Success in RPGs, much like in workplace settings, depends heavily on the right combination of game and people. Rolen highlights the importance of establishing a good company culture to ensure a positive career experience.
- Setting Expectations: The importance of a ‘session zero’, similar to kick-off meetings in projects, is discussed. This involves defining personal goals and shared visions for the game or project to prevent misunderstandings later.
- Empathy and Adaptability: Rolen emphasizes the necessity of being adaptable in conversations, promoting a culture of creativity that welcomes diverse opinions, and encourages problem-solving discussions rather than shut-downs.
- Safety Tools for Communication: Techniques like establishing ‘lines and veils’ (topics to avoid or tone down) and utilizing the ‘X card’ (a tool for players to signal discomfort) create a safe environment for players, paralleling it to maintaining a healthy work environment.
- Team Dynamics and Respect: The speaker shares his experiences of playing with a diverse group across different time zones and highlights the necessity of being culturally aware, which reflects the dynamics of distributed teams in the tech industry.
- Active Listening and Follow-up: Rolen discusses the importance of active listening in both RPGs and software development, demonstrating how paraphrasing helps ensure everyone is aligned.
- Examples from Gameplay: The talk includes narratives from actual gameplay experiences that resonate with team collaboration and the repercussions of various actions taken by characters, illustrating how different styles of play can engage others or lead to disengagement.

In conclusion, Rolen Le advocates using lessons from strategic role-playing to enhance collaboration in software development. Key takeaways include valuing the right team composition, establishing common goals, promoting a safe and open dialogue, and recognizing the diverse influences each team member brings to the table. Understanding these parallels can lead to better communication, teamwork, and overall project success in distributed environments.

Overall, the presentation highlights the importance of strategic collaboration and communication techniques derived from RPGs, recommending these approaches for improving dynamics within distributed software teams.

Dungeons and Collaboration
Rolen Le • November 08, 2022 • Denver, CO

What can fighting goblins teach us about working together? How can going on a perilous journey guide us through our careers? What if I told you I sit in a 4-hour meeting online every Friday night for fun?

Having played Dungeons and Dragons for almost a decade and playing remotely for half that time, I have learned lessons that have taught me how to interact as a developer on a distributed team. From general online etiquette to building great teams, I will discuss tips and tricks of roleplaying that can make someone a better coworker.

RubyConf 2021

00:00:10.400 Welcome to "Dungeons and Collaboration," a player's handbook for working on distributed teams.
00:00:12.240 My name is Rolen Le, and you can find me on Twitter at @RolenTV.
00:00:13.519 I am from Washington, DC. I'm a dad, a husband, a Rubyist, and sometimes a little late.
00:00:15.759 Let's get things kicked off with a session zero, where we can set expectations and get on the same page.
00:00:28.880 What's a tabletop role-playing game? You might have heard of popular ones such as Dungeons and Dragons and Call of Cthulhu.
00:00:35.040 Is it like a tabletop board game? Sort of. Players take turns making moves, but unlike a board game, there's no winner.
00:00:38.079 Is it like an RPG video game? Sort of. You play as characters and tell amazing stories, but you're only limited by your imagination, not what’s in the game.
00:00:46.879 I define it as collaborative storytelling governed by a set of rules, where three to six players act as main characters in a story, and one other player acts as the Game Master or Dungeon Master who facilitates the story.
00:00:59.440 The Game Master controls the game's supporting characters, its terrains, and all the challenges, such as monsters and traps. They also act as a referee and help adjudicate the rules, creating a story by using the rules to help build narrative tension.
00:01:13.760 Now that we know what tabletop role-playing games are, let's get started as I walk you through my journey from 2016 to 2018.
00:01:31.520 First, the tip is to find the right game with the right people. These two elements dictate the majority of my experience.
00:01:38.320 One decides what I do, and the other is who I do it with. This is essential for finding the right company with the right culture, which can either spell success or disaster for my career.
00:01:50.240 Let's take a look at the first half of the equation: the right game. Games are frameworks of rules that help facilitate specific types of play.
00:01:59.520 Scrabble lets people showcase their vocabulary, while Risk allows players to demonstrate their military prowess. RPGs are similar.
00:02:06.159 Some RPGs focus on simulating the world's physics, like how much armor weighs or how fast a horse can run, while others focus more on storytelling, having rules that set clear boundaries and potential consequences.
00:02:20.879 The game I chose was Dungeon World, created in 2012. It's a small indie game that allows players to engage in a high-fantasy setting similar to Dungeons and Dragons but without as many rules.
00:02:35.640 One of the creators originally called it "hipster Dungeons and Dragons." Both games have the same genre conventions, such as wizards and elves, but Dungeon World has fewer rules and gives players more discretion.
00:02:40.560 Dungeon World is powered by The Apocalypse, which means it's a fork of another game called Apocalypse World. This gives it a signature feature, the 2d6 mechanic.
00:02:55.120 First, a player decides what they want to do, for example, "I swing my sword at the goblin." Then the GM prompts the player to make a roll of two six-sided dice.
00:03:01.040 If the sum of the dice is between 10 and 12, the player succeeds, and the GM narrates what happens; for instance, "You slice the goblin, and it falls to the ground." If the roll is between 7 and 9, the player gets what they want but with some added costs; for example, "You slash the goblin, but it stabs you back in the shoulder." And if it's between 2 and 6, the player fails, but the game rewards them with experience to help them level up their character; for example, "Your attack completely misses, and your sword flies out of your hand." So the game allows for players either to succeed or learn from their failures.
00:03:41.600 Now, let's look at the other half of the equation: the energy process of finding a group to play each role-playing game with. Finding the right people is crucial.
00:03:54.959 For example, pre-pandemic, if I wanted to play Dungeons and Dragons in the DC metro area, here are just some of the meetups I could have attended.
00:04:02.480 For Dungeon World, however, there was no dedicated meetup in DC. So how did I pursue my passion that wasn’t available locally?
00:04:16.000 I went to roll20.net, a platform sort of like Zoom but with a digital playmat, allowing you to roll dice and share documents. It also had a great feature that helped me find a group that wanted to play Dungeon World at a time that worked for me.
00:04:26.639 However, just because I found a group didn’t mean they were the right group for me. This starts with setting the right expectations.
00:04:36.080 Just like starting a new job or project, noting what I’m getting into will help manage my happiness. Just like we did earlier, we can have a session zero, where we all get on the same page discussing our personal goals and sharing a vision.
00:04:45.759 For example, are we playing a game that's like "Lord of the Rings" or "Game of Thrones?" Both are fantasy but vastly different. If I go into a game thinking we're going on an epic journey, and halfway through, my party members go off on me, I'm not going to have a great time.
00:05:00.160 We also need to be adaptable. Let's say a player says, "I want to be a pirate." If the GM responds with, "You can’t be a pirate because I want to set my game in the desert," that shuts down the conversation immediately.
00:05:11.600 Starting with a hard no shuts down people's creativity, making them less likely to present ideas in the future. One way to approach this is to never start with no and always ask why, getting to the root of what people want and helping solve their problems instead of just saying no to misaligned tactics.
00:05:27.919 The GM could say, "I was thinking of setting the game in the desert; why do you want to be a pirate?" The player replies, "I want a boat!" The GM could respond, "What if a boat traveled on sand instead of water?" I recommend using this tip when developing features to ensure we know what is being built is done correctly.
00:05:42.080 We also need to make sure we're creating a safe environment for our fellow players, which we can accomplish by using safety tools. One tool is to have a conversation during the session zero, establishing lines and veils. Lines are things that players don’t want to engage with at all.
00:06:09.680 For instance, I personally don't want anything to do with childhood trauma, especially now as a parent.
00:06:13.280 Others are veils; these are topics that might be part of the story but can be glossed over or faded to black. An example would be physical intimacy. It’s okay to mention that characters are romantically involved, but I don’t want to listen to a detailed roleplay of a makeout session.
00:06:30.480 Sometimes things are brought up in play that we didn’t realize bothered us. For that reason, there's the X-card, which originally came from in-person play, where an index card marked with an X would sit in the middle of the table.
00:06:52.320 Any player could pick it up or point to it, signaling they wanted something to be changed that made them uncomfortable. As people have migrated to online play, players can verbally call for an X-card or type an X in chat.
00:07:07.760 I recently read a story online where someone was in the middle of play and realized they were uncomfortable with spiders being in the game. They put an X in chat, and the game quickly noticed, asking for a break, swapping out the spiders for frogs, making the player more comfortable without changing the game drastically.
00:07:21.840 Now that I've talked about role-playing games, let’s walk through an example of a party I found and the adventure we embarked on.
00:07:31.040 Let’s meet the party. We had our game master, Jonathan, and our healer, Hawthorne, played by Lux from Australia. Kaibo, our thief, was played by Josh from Texas.
00:07:39.360 Wisteria, our druid who could turn into any animal, was played by Wussy from California. I played Ury, the wizard, from Washington, DC.
00:07:48.640 We were five people spread across four time zones and two continents, so the least we could do was respect each other's schedules.
00:07:56.319 We played from 5 to 9 PM on Sunday nights, meaning we started at 7 AM Monday morning for Hawthorne, so she needed a bit of extra time to get going.
00:08:08.000 As for me, I normall had to stop at 9 PM to go to sleep and prepare for work the next day.
00:08:18.720 We were also three men and two women of diverse backgrounds, and our ages ranged from our 20s to 40s, necessitating cultural awareness. In my old group, we were all twenty-something guys who shared similar experiences, but playing online opened my mind.
00:08:33.679 I became more mindful about references and things that not everyone at the table might understand. For instance, if I compared a dragon to Charizard, not everyone might recognize that reference, so I should clarify it by describing the dragon's features.
00:08:49.720 Now, let’s flip the perspective a bit. I'll solo role-play while occasionally rolling a six-sided die to keep things interesting.
00:09:05.360 The party has just fought a big dragon, and now I’ve come to town to celebrate our hard-won victory. Where and how should we celebrate in town?
00:09:20.480 1) Drinking in a tavern, 2) Having a barbecue in a park, 3) Attending a wedding reception at a castle, 4) Participating in a parade, 5) Throwing a gala on a rooftop, or 6) Having a dance party at a wizard's tower.
00:09:45.920 What did the dice say? Five! A gala on a rooftop!
00:09:48.080 The entire party is at this event in their most regal outfits. Kaibo is at the bar doing shots with the staff behind the counter.
00:09:57.760 Hawthorne is being a great diplomat, greeting all the new guests. Ury has someone cornered, boasting about how he single-handedly slayed the dragon, and no one else helped.
00:10:05.600 Meanwhile, Wisteria is transformed into a beautiful eagle, flying around and taking in the surrounding view from the rooftop.
00:10:22.720 A dwarf can be heard climbing up the stairs. He appears before the adventurers breathlessly.
00:10:43.200 "Greetings, adventurers! I'm Max Overflow, head of the town guard.
00:10:45.279 Our herbalist, Bergeron Johnson, has been kidnapped by a group of baddies. Our town guard isn’t prepared for this kind of trouble, so you’re our only hope! Our intel suggests that the kidnappers are in a cabin in the woods, so go to the shopkeeper Ada, and she'll outfit you with anything you need before making your way to rescue him."
00:11:00.360 The party accepts the mission. Remember to use descriptive language when conveying a situation. The more detailed something is, the easier it becomes for us to establish a shared vision.
00:11:13.440 Similar to software development, providing a stack trace is far better than saying, "It just doesn't work," and a detailed user story is much more effective than saying, "Make it pop." Let’s fast forward to the shop.
00:11:29.120 The party enters a fairly small shop with a counter directly across from them and shelves containing basic goods, clothes, adventuring gear, and mundane equipment.
00:11:32.880 However, there is one item on the shelf that stands out. What weapon would that be? One: The Sword of Truth, Two: The Prestidigitation Bow, Three: The Non-fungible Throwing Axe, Four: The Free Britney Spear, Five: The Flail Whale, or Six: Chekhov's Gun?
00:11:51.760 The answer is Chekhov's Gun! Let’s write that down. Behind the counter stands an older looking woman with yellowish skin. She jumps out of her chair and says, "Well hello there! You must be the adventurers Axle mentioned. Anything unique is on the house!"
00:12:02.959 As she turns around to reach for the top shelf, the party notices she is missing part of her ring finger on her left hand. If she has her hands, they bear visible scarring; however, she quickly checks to see if there's anything else they need. "Those woods are very dangerous," she warns.
00:12:48.320 It's crucial to reiterate key details. Audio may cut out, or the listener may misunderstand something the first time. Even if the listener hears everything, restating it reinforces the point and distinguishes it from minor details.
00:13:09.040 "Nope, I'm fine," the party responds. Hawthorne approaches the counter and offers to help lessen the scarring on her hand, acknowledging that while she can’t bring back her finger, healing it would lessen the pain.
00:13:22.240 "Thank you for your offer, but I'm fine as I am. This serves as a nice reminder of all the fun I've had. I mentioned you're an adventurer; do you know anything about the woods?" The shopkeeper responds, "Indeed, I've seen many dangerous things in those woods. Some hide in the trees, others in the bushes. Always be on the lookout!"
00:13:54.080 Thank you; I’ll keep an eye out for anything lurking in the trees and bushes. Active listening is a technique where the listener focuses on what and how the speaker says something, then paraphrases it in their own words.
00:14:21.120 I found this especially useful in both software development and role-playing because it acts as a checksum to ensure everyone is on the same page.
00:14:34.160 Kaibo notices Chekhov's Gun on the wall; it's a simple, smooth pistol that feels familiar. “Ah, you like the look of that?" the shopkeeper says. "I acquired it in my last adventure; it’s yours if you want it."
00:14:46.720 "Is there anything I can do to help get our herbalist back?" she offers. "Thank you!" The party continues walking. They leave the shop and start to make their way to the cabin, but now need to set up camp.
00:15:00.160 The party gently discusses what to do next, and Ury, expressing confidence after fighting a dragon, declares, "I can handle a simple rescue mission. I'll sneak off and save Bergeron Johnson all by myself!" The onion-bod visceral can be heard laughing.
00:15:28.320 As they approach to observe, they spot two baddies on patrol. What do you do, Ury?" I blast both of them with a fireball," he declares confidently. "Awesome, make a roll!" "Eleven; success! If they turn to ash!"
00:15:51.840 "What do you do now?" They continue to move closer to the herbalist. Ury arrives at the entrance where Bergeron is being held, observing two enemies guarding the entrance. "What do you do?" "I cast Magic Missile on one of them," he responds.
00:16:10.720 "Partial success." You manage to take one down, but the other knocks the wand from your hand. "Well, I take out the other one!" "Success! They are both taken out! What do you do?" "I burst into the room and scream, "Relief! Ury is here to save you!"
00:16:24.160 Now, while this series of events may seem thrilling for Ury, the other three players could very well be disengaged, likely checking Twitter or being on their phones.
00:16:37.440 It becomes difficult to pull them back in. Similar to the tech world, don’t be a rock star in RPGs; don’t hug the spotlight.
00:16:54.480 Everyone contributes and adds to the excitement of the experience. Back in the cabin, Ury sees and smells dark gas filling the air and starts to feel lightheaded.
00:17:07.440 "What do you do?" Ury says, "I hold my breath and cover my mouth with my jacket." "Failure; you pass out!" Let’s check back in with the rest of the group.
00:17:18.560 The party wakes up to the sound of an explosion and a flash of light from the farm, as if someone just cast a fireball. Kaibo whispers under his breath, "What the heck just happened?"
00:17:36.160 Hawthorne speaks up, saying, "The shopkeeper mentioned that the baddies could be hiding anywhere! Wisteria, can you scout ahead and see what's going on?" That's a fantastic idea!
00:17:46.960 "I'll turn into a bird and keep a low profile." Wisteria flies around and spies two baddies hiding in the bushes.
00:18:02.160 What’s up with that wizard rushing in? What an idiot! Doesn’t he know anyone can hide in trees and bushes?" Wisteria returns to the group and tells them what's going on.
00:18:23.840 "Coco, what do you do?" I sneak over and pull out Chekhov's Gun and take out one scout before quietly taking out the other!
00:18:31.680 Success! You take out both. Hawthorne, what do you do?" "I go to one of the corpses and cast Speak with the Dead. This allows me to ask a corpse three questions they must answer truthfully.
00:18:43.760 The first question is, "Where is Jerry?" The corpse answers, "The boss probably has him." The second question is, "Who’s your boss?" His answer is, "He's a Mind Flayer." The last question is, "How do we defeat him?" The answer is, "He's afraid of spiders."
00:19:04.560 With this information, the party quickly approaches the cabin. What do you all do next?" Ury turns into a spider and sneaks into the cabin.
00:19:24.000 Inside the cabin, you see Ury struggle with Pascal’s contest, which has turned into a mind control scenario. The Mind Flayer is scheming about how to control the herbalist, convincing everyone that medicine is bad.
00:19:38.400 Wisteria, what do you do?" "I jump on him and scream, 'You hippie!'" Kaibo, what do you do?" "I sneak into the room with my Chekhov's Gun drawn.
00:19:53.760 Hawthorne, what do you do?" I follow closely behind Kaibo. Remember to play off each other’s actions, just like in software development. Everyone contributes with different skills, so it’s best to work together.
00:20:09.920 As the encounter unfolds, the Mind Flayer is caught off guard and ultimately defeated. Afterward, everyone reflects on the adventure.
00:20:20.320 The moderator mentions they were researching in the woods when the Mind Flayer and his goons captured him. Before that, he found Stones of Far Speech which allow him to communicate with all of you.
00:20:26.640 The players thank him for the gift. At the end of the session, we usually ask three questions, and for each yes, we gain a point of experience.
00:20:35.440 Did we uncover treasure? Yes! The gifts we received! Did we overcome a notable enemy or monster? Yes, we defeated the Mind Flayer. Did we learn something new about the world? Yes, we learned a ton of valuable lessons.
00:20:51.760 For example, we discovered the importance of finding the right group of people, being empathetic, and playing off each other's skills to enhance our remote collaboration.
00:21:11.328 When I originally gave this talk four years ago, our party was in the middle of our campaign, experiencing a high point of fun.
00:21:21.760 However, our campaign has been over for three years. I wanted to do a tabletop version of a retro called "Roses and Thorns," where we discussed things that worked for us and things that didn’t.
00:21:30.960 Let's start with Roses. We completed the campaign, the first time I've ever accomplished that. Even groups with great chemistry don’t always finish because life can get in the way.
00:21:43.040 The satisfaction of wrapping up our story with an epic in-game battle felt great. Also, I turned random people from the internet into friends—people I still keep in touch with. I even send them Christmas cards every year.
00:21:57.920 What didn’t go well? We started a new campaign, but it wasn’t the same as before. We were the same people plus one new addition, but different roles. The quirky player became the brooding one, the jokester became the straight man, and the gloomy person became a silent loner.
00:22:15.840 We struggled to click and didn’t have as much fun. We also experienced burnout after playing non-stop for two years; we began running out of creative juices.
00:22:29.600 We tried to keep things fresh by taking breaks and playing other games. However, it became difficult to continue after Lux got a new job, and I was expecting my daughter.
00:22:43.680 This whole experience has been one of the most enjoyable things I've ever done. I am proud to have been part of this party. I want to thank Josh, Jonathan, Lux, and especially Wussy, who created all the art for this.
00:22:52.960 Thank you for your time, and have fun gaming!
Rolen Le
@rolentle
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