XO Ruby San Diego 2025 - Dungeons and Developers: Uniting Experience Levels... by Chantelle Isaacs

What is discussed, and when

1. 0:00 – 5:00: Dungeons and Dragons, Ascent, Chantel, Chantel Issacs
2. 5:00 – 10:00: Dungeons and Dragons, Dimension 20, Exor Ruby
3. 10:00 – 15:00: Dungeons and Dragons, Exor Ruby
4. 15:00 – 20:00: Dungeons and Dragons
5. 35:00 – 40:00: Dungeons and Dragons
6. 45:00 – 49:58: Chantel

Notable quotes from "XO Ruby San Diego 2025 - Dungeons and Developers: Uniting Experience Levels... by Chantelle Isaacs"

• Thanks y'all. hi friends. My name is Chantel Issacs. I met Jim and several other people in the room in my time at Learn Academy. Wait, there's a better photo. so AI is great for certain things, let me just say.

  about Chantel · at 0:20

• Raise your hands, zero to five fingers, how familiar are you with Dungeons and Dragons?

  about Dungeons and Dragons · at 1:41

• With my interest in Dungeons and Dragons probably only about five years ago. I was watching Dimension 20, this lovely troop down here, and I was This sounds super fun. I want…

  about Dimension 20 · at 7:07

• And the imagination of everything. So why would we talk about Dungeons and Dragons? at exor ruby. so there's a couple things that I in my background working with junior…

  about Exor Ruby · at 8:02

Who and what is mentioned in this episode?

People

• Chantel — Person · 2 mentions · first at 0:23
• Chantel Issacs — Person · 1 mention · first at 0:23
  Thanks y'all. hi friends. My name is Chantel Issacs. I met Jim and several other people in the room in my time at Learn Academy. Wait, there's a better photo. so AI is great for certain things, let me just say.
• Killbilly Jim — Person · 1 mention

Companies & orgs

• Exor Ruby — Company · 2 mentions · first at 8:08
• Learn Academy — Company · 1 mention · first at 0:29
  Chantel Issacs. I met Jim and several other people in the room in my time at Learn Academy. Wait, there's a better photo. so AI is great for certain things, let me just say.…
• Ascent — Company · 1 mention · first at 0:56
  Academy is ends a little sadly but the connections that I made there landed me currently at Ascent. That is my day job. Ascent does a very sexy thing called student loans. but…
• Dimension 20 — Company · 1 mention · first at 7:11

Concepts & topics

• Dungeons and Dragons — Concept · 12 mentions · first at 1:46

Full transcript with timestamps

0:20 Thanks y'all. Um, hi friends. My name is Chantel Issacs. Um, I met Jim and several other people in the room in my time at Learn Academy. Wait, there's a better photo. Um, so AI is great for certain things, let me just say. Uh, making me look like a sorcerer is one of them. So, I met Jim during my time at Learn Academy, um, where he was helping, uh, some of our students get their internships. Um the saga of learn academy is ends a little sadly but uh the connections that I made there landed me currently at Ascent. That is my day job. Ascent uh does a very sexy thing called student loans. Um but uh my job allows me to travel uh around and attend other conferences. So uh the talk that you guys are hearing today started in the tech space uh as Dungeons and Developers. I've modified it to fit different uh demographics of people and it was a fun return back to the tech uh context for the event today. Um as I've

1:26 modified this talk, I was like, "Hey, this is really fun and I've turned it into my side gig, which is skill check coaching." So, I put that on there, too. Um but I love doing this. Um so, to get started, I want to orient myself to all of your understanding. If you could all raise your hands, zero to five fingers, how familiar are you with Dungeons and Dragons? There's a lot of fives in this room. I shouldn't be surprised. Um, I'm seeing a couple ones and twos and zeros. Wonderful. Um, so, uh, a shout out. Okay, 10 over there. Wonderful. Uh, love it. So, I would love a volunteer from someone who is of a lower number.

2:09 Vanessa, please come help me. Yes, you're coming up. Can I steal this from you? Vanessa, I want you to imagine a character.

2:20 What? No. A character. A character. A character. Are you like you are uh going to create right now? We're envisioning a Dungeons and Dragons character.

2:29 Um are you uh are you tall? Are you short? Are you strong? Are you sleek? Are you Tell me a little bit. We're inventing something off the fly.

2:38 Cool. I think I'm tall and I'm strong. Tall and strong. Wonderful. Uh, what kind of weapon would you have? Are you more of a sword type of uh, person or bow and arrow or daggers or what are what are we talking here?

2:50 Sword. Sword. Yeah. Tall sword. Uh, are we male, female, non-binary? Like are we are we a like a cat person? Um, tell me what

3:01 how about gender fluid? Gender fluid. Love it. So, you are our gender fluid. tall, strong, sorted uh hero. And right now you are in the dark. Oh, that it doesn't project as well. It is night time. You are in a forest. You are walking a path.

3:17 The sun, the moon is trickling through the trees. Ooh, atmosphere. Good lighting.

3:23 Uh, and Dungeons and Dragons is nothing without dice. These are for you, but I'm going to need you to roll that one for me. So, you are in the woods. Um, it is dark. It is very quiet. You are alone. What are how are you walking through the woods? Are you feeling very confident in yourself or are you feeling like I should stay quiet or uh

3:46 I think I am confidently getting the lay of the land. So, I'm staying quiet. Okay.

3:51 And evaluating what's happening around me. Wonderful. So, you are trying to stay quiet though. You're not You're not trying You're not like just stomping through the woods big and tall and strong with your sword. Okay. So, we're going to do a stealth check. This is now the start of Dungeons and Dragons. I would like you to roll that. And depending on how well the higher the how high the number is will determine how successful you are at being stealthy. So, go ahead and roll.

4:17 Um where where uh on a chair on the floor and tell us what it says. Um if it's cocked, go. If it's cocked, roll again. The chair maybe not is the best place.

4:33 It's a five. It's a five. Unfortunately, um there are many dry sticks on the path and you are making noise as you walk along. Um that noise uh alerts something in the woods and you hear a growl. What do you do?

4:51 I pull out my sword. Wonderful. You pull out your sword. So, uh go ahead and uh let's do an investigation check. You pull out your sword. You hear a growl. We're going to see if you can see what is making this growl. So, go ahead. Let's use the floor this time.

5:08 Is that a six? That is a six. No, that's a nine. That is a nine. Okay. Um, it's still really dark. A nine is from 1 to 20. A nine is still below our midpoint. So, um, you see maybe a dark shadow, but you cannot tell anything about it. You can't tell how big it is. You can't tell how small it is. and you are there sword drawn and you're waiting. Out of the shadows comes a very large monster uh called an owl bear. It is exactly what you would think it is. It's a bear like feathered uh like kind of fur owly face. This is not a thing you want to mess with. Uh you see this monster. What do you do when you see what it is that is coming towards you?

5:52 Um, I brandish my sword. You brandish your sword. So, you hold it out. Are you trying to like look intimidating?

6:01 Yeah. All right. Let's see how intimidating you look. So, we're going to roll for that.

6:10 Is that a nine again? That does look like a nine again. Uh, these dice don't seem to like you and that's okay. That's part of the beauty of Dn D. So, uh, thank you for assisting me. I don't want to take up the whole time us role playinging solo. Everyone give Vanessa a hand in here. I blew on them. They're more lucky now. Uh those are for you. Uh so that's Dungeons and Dragons. For the zeros in front of here, the Dungeons and Dragons is just playing fantasy pretend with Dyson rules. All right, that's all it is. You pick a scenario. Are you in the woods? Are you in a city? Are you in a cave? Are you fighting a dragon? uh and you and other players are being led through an adventure by someone called your dungeon master. They are your guide or your maestro, whatever you want to call it. Uh Dungeons and Dragons uh is 50 years old. Uh but it has definitely come back into the zeitgeist more um in

7:04 the past 10 years or so. I got started with my interest in Dungeons and Dragons probably only about five years ago. I was watching Dimension 20, this lovely troop down here, and I was like, "This sounds super fun. I want to play." I had no one to play with, so I just dove in and like found some friends and became a DM for the first time. Um, I fell in love with it. It's so much fun. It's so fun to play with other people. It's a way to live vicariously through another character. Uh, I have a three-year-old at home. He's three. Can you believe it?

7:35 Um, and playing pretend with him is hard. Uh there is a level of uh you oh yes you're serving me spaghetti and yum it's delicious. There's not enough structure for me to dive into the playing pretend with him. Um parenting has its has its things and I cannot wait until I can teach him this because it is the playing pretend that I know I can guide him into and the imagination of everything. So why would we talk about Dungeons and Dragons? uh at exor ruby. Um so there's a couple things that I uh in my background working with junior developers at a boot camp. I did career services with them. So what that means is I was working with them on their resumes, on their interview skills, on talking about what brought them into the desire to switch into tech from whatever their prior career was. And as I'm talking with them about their skills and abilities, I was like, "This is kind of like building a character sheet." um

8:37 looking at and assessing the skills that you have and how you talk about them and how they translate into the thing you're trying to do now. All of that really resonated with me as I was playing D and D a ton and working with these students. So what that looks like first off is roles. Everybody has a role on the team. Your role is distinct and it helps define your part in completing the quest that's in front of you. In addition, everybody has unique skills. So your role is one thing. The skills that you bring to that role are separate. So what does it look like to leverage the unique abilities that everybody has?

9:16 Finally, you don't want to just be solo on a project. You want to be working with other people. You want to be thinking about the uh resources that you have in the people around you and collaborating to achieve goals together. And also, you don't want a clone of you in every single thing. Sometimes you might, depending on who you're working with, but odds are the diversity makes the team stronger. And so recognizing that the varied perspectives that are around you makes the team stronger and more equipped. So all of that in a tech perspective um should feel somewhat familiar to all of you. You all know what it's looked like to work with different people, to work across crossf functionally with different teams. Um, and now we're going to turn that into what that looks like to carry forward to be intentional with it. So, first off, there are a ton of roles that uh you all can fit into. Um, we're going to start

10:12 handing these around. Jim, if I could have your assistance, please, because you guys are going to fill out a character sheet. Um so first off this is Exor Ruby. So we of course need to start with our backend engineers who are our wizards. Um you guys have all the knowledge and uh everything you need to orchestrate the structure of app development etc. Um and processing it with technical mastery. I talk about wizards. They are magic users who have to know they they build their magic through knowledge and book learning. Um, on the f uh flip side, our front-end engineers are our sorcerers. Um, they weave the visible interactive elements of the application. I like to say when Hagrid uh says to Harry Potter, "You're a wizard, Harry." That was a lie. Harry Potter is a sorcerer, not a wizard.

11:05 Harry had this innate ability, and that is a sorcerer trait. Um, oh, oh, wonderful. I was like, "Wait, everything is broken." I know you don't want to crowd around my laptop to look at the slides. So, uh, up next we have our bards. Our bards are our designers. Bards are the ones who weave stories. Um, they craft compelling user experiences, um, with creativity and with artistry. Um, our barbarians are a QA. They hit stuff till it breaks. Um, they stress test and ensure that software is robust. Um, I love that. That one always gets laughed and it makes me happy because I play a barbarian and it's I hit stuff till it breaks and it's awesome. Um, fighters are our team leads. They are the strategists. They know have to know the different aspects of things and lead a team with strength and strategic acumen.

12:02 Our project managers are our rogues. They are the ones who have to navigate through projects with agility and strategic foresight. They are the stabby stabby in the dark. They have the daggers and they can lockpick and they have to figure out how to get everyone in the same place at the same time with all the obstacles that are around. On the product side are our druids. Druids are the ones who are like one with nature and they get their na magical abilities from nature. They have to maintain the balance between what the user needs, what we actually can do, what the business is asking for and how technically feasible all of it is.

12:37 And last but absolutely not least, DevOps is our clerics. They support the applications infrastructure with the healing and enchantment. Uh so I am always the person who loves to take the personality quiz when I open a magazine. I hope you have now stereotyped yourself and maybe the people around you with some of these. On that note though, how many of you feel like you fit into more than one of these categories? More than half of you are raising your hands. So we will talk about multiclassing shortly. Um but those are some of the uh roles that exist on a dev team. Uh it is by no means exhaustive but I have 30 minutes for a talk. So uh if you are feeling like um where is the paladins? We can talk later. Um because there was a lot of fives in the room. I know you all are checking my work. Um, so knowing what your role is or the multi-rolls that shoes that you fill on your team is just one piece. You

13:37 also have an idea of who you're surrounded by. Um, and it doesn't matter what role you play if you don't know what makes you good at it, right? So, we're going to talk about the skills and abilities. And this is really where you can start to kind of follow along with different elements um on this. It's a I kept my workplace character sheet rebranding it all for developer character sheet. I found out I was talking 24 hours ago. So, you know, you work with what you got. Um, so there are six abilities that your character in Dungeons and Dragons has. They are strength dexterity constitution intelligence, wisdom, and charisma.

14:18 For those of you who are probably like zeros, ones, twos, threes, those are random words and they mean nothing to all of you. So, I will explain what they are using the tomato analogy. Strength is how many tomatoes you could carry. Dexterity is how many tomatoes you could do. Constitution is how many tomatoes you can get hit by before you go down. Intelligence is knowing tomatoes are a fruit, not a vegetable. Wisdom is knowing do not put tomatoes into a fruit salad. And charisma is being able to sell a tomato-based fruit salad.

14:54 salsa. Salsa is a tomato based fruit salad. Um, so looking at each of these, what I've done is I've taken them and translated them from our world of uh Dungeons and Dragons into these are soft skills. These are things that we all have in various capacities. And as you're looking at your character sheet, what I would like you to do, and you can listen and fill this out later, but the idea here is we're going to go over these are the abilities. And all of these abilities have subs skills underneath them. And what I would like for you to do because rules and constraints are important is you will bubble in seven things. Five are regular little bubbles.

15:34 Two are stars. Your regular little bubbles are I'm really good at this. Your two stars are the I'm really freaking good at this. All right? Like I give myself props for these things. You will understand how that plays into a team uh evaluation shortly. So with strength, strength translates over to drive. What keeps you moving? What is the force behind the initiatives that you have? What's the thing that gives you the energy to keep moving forward? How do you overcome the obstacles that are in front of you? Um and the skill that's underneath strength is athletics.

16:12 Being able to be athletic. Do you just jump over the creek or do you like do a backflip over the creek? Right? Uh is execution. So thinking about if you have high drive, then you should have high execution, right? Um up next, dexterity. Dexterity has to do with agility and reflexes. Dexterity translates over to efficiency. How efficient are you? Can you navigate complex tasks? Can you manage your time effectively? And how um adaptable are you when all of a sudden things change on the fly? So acrobatics, slight of hand, and stealth are the D&D traits. That's adaptability, precision, and discretion on the personal side. Um how adaptable are you when things go ary um or all of a sudden deadlines get moved up? Um the precision that you have in writing code. We all know that there's only so much that uh different mods and stuff can do in our idees to help us uh with our syntax and we have to be precise with things. Um discretion

17:16 I think of hey stuff is blown up in prod and uh how fast can you fix it and do you need to raise a raise the flags immediately or is it a quick fix that you can do and bring awareness to the team after you've come to a solution and knowing the difference of when you need to do each of those. Dexterity also plays into your armor class. So if you think about if someone has high dexterity, they probably are going to be able to avoid getting hit by arrows or someone swings a sword at them. So your armor class uh is if if you are thinking in terms of like a knight, if they've got good armor and they get hit by something, it's probably not going to do them damage. Okay. In the real world, armor class is stress resistance.

18:03 How resistant are you to stress? Do you have the ability to avoid workplace stressors? Can you be organized? Again, with that adaptability, uh, can you prioritize and manage your time? Can you protect the well-being of yourself to prevent stress from landing? Water off a duck's back. I've got this. I know that I have a good amount of efficiency that then helps me resist stress. Right? So in this um coming up with a metric for you guys to measure your stress resistance is hard. Um so what I would like you to do is just give yourself a scale of 10. Put a number in there or bubble in your little uh shield icon as much as you feel is appropriate. And this is a here and now thing. Maybe you are feeling very recharged from attending this event today. And you're feeling like, yeah, I'm I'm good. My stress resistance is high. Uh maybe there's other things going on. And again, this is a measure of the here and

18:58 now. So take that with a grain of salt. Moving over to constitution, how many tomatoes you can get hit by before you go down. Constitution translates to resilience. And resilience now because stress is real and stress does land has to do with how we handle it. What are the things we do to bounce back from it? How are we uh maintaining our composure? How are we keeping our spirits high? and how are we facing the challenges in a way that keeps us motivated. So that translates to our hit points in Dungeons and Dragons. Someone who is big and beefy and strong has more hit points than someone who is focused on their stealth and they're like sneaky and like lockpicking for the team or even someone who's casting magic from the the back and they're needing their teammates to be in front of them. Um so our resilience has to do with our hit points and our stress tolerance. So how are you uh tolerating when challenges hit? How

19:56 are you tolerating the attack of tight deadlines? How are you tolerating when hey you are as efficient as possible but suddenly things go crazy and you know things get stressful or it's a time of year when you know that you have to get stuff done by a certain point of time. So what is the uh how are you evaluating yourself with the amount that you can tolerate and then and in addition how that pairs with how you're resisting it in the first place. Does that make sense? Cool. Intelligence. This is this translates over to knowledge. You have to know the syntax. You have to know the frameworks.

20:32 You have to know the architecture that makes things run. and how does that then translate with innovation, the contextual awareness, analysis, systems thinking, value values alignment. That's a lot there. But thinking about, hey, what are the new things I can learn and be innovative in the structure that I'm in? Um, what awareness do I need to have of like historical context, where we've moved from to where we are now, or what's the context of where we're trying to go to build things in a way that uh makes sense both in the short and the long term. Um, data is a part of what we work with. Be that something in the databases that we're connecting with through APIs or just numbers. Uh, I look at Excel sheets a lot. And, uh, being able to look at and analyze data in a way that's helpful to my team is a really important thing. Systems thinking, what are we using? What do we how do they work together? Understanding

21:24 those pieces and also thinking about what exists out there. Um, are there new things that we can implement that make our jobs easier? Uh and then values alignment is the way that uh things are being built now in alignment with your own personal values. And this bleeds into the wisdom category we'll talk about next. But also um is it in alignment with the values of the people around you and the values of the company and what they say they uh promote or working towards. Wisdom translates over to discernment. Wisdom don't put tomatoes in a fruit salad. Um, perceptiveness and mental fortitude is what we think about when we think about wisdom. So, discernment is all about your judgment. Can you solve problems creatively and make informed decisions? This comes into empathy, emotional intelligence, support, awareness, and risk management. Um, again, empathy. This is not only for yourself. Self-mpathy is important, I

22:21 think, but the people around you, who's on your team, um the people you're serving, um the customers uh who are using your product, um emotional intelligence, being aware of the human beings that we surround ourselves with both in and outside of the workplace, um how are we aware of their needs and being cognizant of that and compassionate towards them as people? Um support, are you aware of when people need a helping hand? That could just be a hey I found this tool I think will help you or that could be sitting by them when they're debugging something that's really rough. Are you somewhere someone who is uh supportive of the people around you? Um tied to that is just awareness. Do you know what's going on?

23:03 Are you someone who is head down and like getting your own stuff done which is fine. Or are you someone who if someone asks about a tangental project, they ask about a tangental project and you're like, "Oh yeah, they're working on this and this and this." Just because you have that awareness, you are asking the questions or you're listening in the meetings to know like how things are affecting each other and how things connect. Uh and then of course risk management. Uh the last thing we want is to push something that we shouldn't have. uh and being aware of how different aspects impact other things, how what the connectedness is um not only in the code that we write but also in the overall context of how this affects the business, the company, the overall uh like long-term project goals and timelines. Um how are we aware of the impact of those things?

23:57 And then finally is charisma. Um charisma translates to communication. Charisma is about charming people. Bards are the charismatic ones in D and D. They are the ones who are telling stories or singing songs or weaving ballads. Um and uh the career charismatic skills, deception, intimidation performance persuasion. Um that's negotiating. How are you able to negotiate? Fill in the blank. Your time off, a raise, or just negotiate the pros and cons of a decision um that may or may not make your job easier or harder. um and presenting that that goes into presentation. How are you presenting data? Are you coming to events like this and giving a talk or are you signing up to speak at other conferences or is it just hey I have to show like the progress in a project in a board meeting and you need to present there. uh being assertive. Sometimes we know when we're right, how are we presenting that or how are we advocating

24:57 for the people around us or the the decisions that are being made that we know we need to stand behind? Uh and then influence um being influential and that's not only in the sense of [snorts] code but also in the sense of uh guiding people towards u the best decision that you can uh that you've come up with. Maybe that's helping uh be an advocate for those around you. So, those are our abilities and skills. Again, you can take the time now or later. We have five bubbles and two stars. Filling in the rest of the page, things to think about. So, first up is tools and proficiencies. Um Vanessa had a sword that she was ready to brandish at the owl bear. Um tool proficiencies are things like the tech that you use. And this is outside of just your IDE. These are the uh call it uh ancillary um things. So are you really great at Excel? You know, Excel formulas, you can like whip those up and you can share

25:58 something. Not everybody is and that's fine. But hey, is this something that you know that people would come to for help? This is another way of uh maybe filling this in is if people keep asking you for help with a thing, maybe that's something you're good at. Um so uh data visualization with things like Tableau. um using Figma to design things or piece together a uh like a project outline. Um Adobe be that Photoshop or um uh Final Cut Pro or whoever whatever else is in Adobe's massive uh uh list of products, but what are the things outside of just what you use to write the code that you write that you are good at? What are the tools that you use?

26:42 Next up are special abilities. Who here's really good at naming things in the back? Yes. Uh, some people are really, really bad at naming things. How often have you opened something and you're like, "What is this? I don't I I don't understand what this uh like method is trying to do. It is so uh unintuitive. I I don't get it." Um, I have worked with people who for some reason they can always find the time that everyone can meet for a meeting. They are the calendar wizards. This is outside of again the tech. This is all about the uh the stuff that you are just good at. Um some people are really good at being a rubber duck. Is anyone not familiar with what a rubber duck is?

27:23 Yeah, I use instead of a rubber duck. Hey, whatever works, right? Some maybe Megatron just gives you better advice than your duck and that's fine. Um but some people are really good at being a living rubber duck and they can sit there and ask you the right questions to get you to the solution that you need. Um, Eli5, this is something that I would take as a special ability. It stands for explain like I'm five. If you're not on Reddit, um, like I am. Being able to explain things or take an idea and dumb it down to if you were explaining to a 5-year-old and make them understand.

27:57 That's not necessarily that the person needs it, like they're only 5 years old, but finding the key concepts or the analogies that make people go, "Oh, I get it now." I'm very proud of that. And myself, I would put that in my special abilities. So what are the special abilities that you have that you can identify resources? Again, these are this is now coming outside of you. What are the things that surround you that make you great at your job? So having really good mentorship, do you have a mentor that just is always the best sounding board that you could imagine? Do you have someone that um always points you in the right direction? professional networks coming to events like this um or uh other uh what's the word I'm looking for? Maybe there's like a monthly happy hour that you always attend and you know that that's some a great place for you to connect with people in in and outside of your industry. Does your company

28:52 prioritize having really good onboarding documents or wikis or things like that? That's a resource that's outside of you that can help you be good at your job. I put this one on here for me, too. I have a flexible schedule. I mentioned having a three-year-old. I'm in the office only two days a week, but I know that if some mornings are rougher than others, um my husband is full-time daddy and he's amazing. But, uh it sometimes two parents being around as the day is getting started is helpful. And I know if I'm rolling into the office at 10:00 a.m., no [clears throat] one's blinking an eye. I have that flexible schedule. I have that understanding to like do what I need to do in the hours that I have.

29:29 And that is something that I I do not take for granted. So, what are the resources, the external things from you that help you be awesome at what you do? What's your current quest? What are you focused on? What's the goal that you're pursuing? What challenge are you trying to overcome? Um, what is it you're trying to create? How are you trying to be innovative? What is the quest that you find yourself on? And again, this is in the here and now. This is hopefully going to be different in a month, three months, a year. Um, it evolves. But what are what is it that right now has your attention?

30:05 And then finally background. How many here people here actually started their like tech career as like a CS degree? Not not the majority. How many here started in like remembers their first job in like food service? Yeah.

30:23 Like say first job. Yeah. No. um or like the I this is one of the things that from working with people transitioning into tech, I worked with people in the military. I worked with people who were in food service or truck drivers or train engineers or fill in the blank. It was so vast and diverse. I worked with people who had a career and then became parents and had to stop working for a while and now they're trying to get back into the workforce and they're using this as a way to upskill. the the what we bring from our previous roles matters, right? What are the things that you learned or were taught? And this is where maybe some of those tool proficiencies that you have come come from. Maybe this is an awareness of um needs or an awareness of the the differences that you may be interacting with. Um parents' jobs. I grew up overseas. My parents were missionaries in Africa. that watching them in that

31:19 context is definitely a part of my background and gives me context to the people uh that I interact with the the values that they imparted upon me um the various cultures that I saw growing up like that is part of my background and it influences how I do my job today it influences who I am as a person into that did you study abroad or did you travel what are things that impacted you from outside of the bubble that we live in on a day-to-day what are the things that have given you a new perspective um upbringing. Again, maybe this is has to do with you were raised more by a sibling than you were by your parents or your grandparents or you were super involved uh this it could be you were super involved in after school activities and you just did all of that and you were super engaged in that and like contributed in that way. How are what are the things about your upbringing? Um having been a missionary

32:09 kid overseas, we didn't have restaurants that could cater our school events. So, if we were going to have a a thing, that meant at 9:00 am we were in the school kitchen like chopping onions to make a spaghetti dinner. Like, so it's a random thing, but those skills coming in from my upbringing are something that I bring in with me. How that applies in chopping onions in my current day job, I'm not sure yet, but it's there, right? Um, and maybe that's just being uh part of a team and stepping in and volunteering. Those are things that come from that upbringing. So what are those things that you bring? That concludes the sheet for you. But what does that look like when we talk about a team? Because I um have had the privilege of doing this type of exercise with a whole team um at a uni at a at a community college up in Northern California. It was incredible.

33:00 And it was 24 people and I actually taught them how to play D and D. And then we did this and what they did because it was admissions and financial aid and like veteran support and EOPS, which is like support services for like foster kids, that sort of thing. Um, so it was all these different departments that came in and we did this and they did this uh assessment of themselves and then we did a skill inventory and it was so cool because they had these bubbles and they were like, "Okay, I picked this and this and this for myself." And they were like, "Wait, you didn't pick innovative? we're putting that down for you. It was incredible to see how they were supporting and uplifting each other in this skills inventory of, hey, what did you self- select, but what do we see in each other? And then doing this to assess where the team as a whole self assessed as really strong or didn't self assess and noticed some weakness. So,

33:51 there's a ton of ways to do this. I've provided you a very nerdy D&D way of doing it. Um, strengthfinder is a very pro uh common method and if you do it as a team, you can do this based on the one through five or even one through 10 numbers that people get. Uh, I'm going to breeze through these slides because these are all just examples. This isn't a lesson in StrengthFinder. Um, but some people just use Excel and they make a ma a matrix and you pick the skills that you're looking at that you want to assess and you you come up with the values and how you want to uh align those. I've seen uh baseball cards as another method of doing this where it's just, hey, maybe you and your team are super sporty and this connects with you.

34:32 This guy, don't talk to him about organization or time management, but if you've got a problem, uh Ethan can solve it. So, go Ethan. Um SFIA8. This is a very cool system that looks at technical skills, what the precursors are, and what uh you can use to like be building things up. So, it's a forward thinking method. I've done tons of research. Durable skills is a very popular one as well um with 10 primary categories and then the subcategories underneath it. You find what works for you. And what we did with this uh was what what I created to align with the sheets you guys have and I'm happy to share this PDF if you want to use it. Um is looking at the five categories because constitution and resilience is its own thing. Um, but then they filled in their names and they filled in is it one point or two points and they totaled everything up. Um, and it was so cool to see again where they self assessed is really high and um

35:31 where they'd notice gaps. There was one category it fully escapes me which one it was that um nobody picked and they were like does this mean we all suck at this? And in that conversation they realized that it wasn't that um nobody had it. it was that it was a preassumed um just value of the team. So instead of people selecting it, it was actually that determined that they were pretty strong in it because everyone just kind of they disregarded it because it was just presupposed. And so even just those conversations around high, low, what why is that? And that beautiful thing of empowering each other of I see this in you. We're putting that on there. You didn't put it on your sheet. We're giving you the points for that. Um was beautiful to behold. What do you do with that then? Because then you've got this information. What do you use? How do you use that to plan for success?

36:22 SWAT analysis is an easy way that you can use this. Where are you strong? Where are you weak? What does it look like for opportunities on your team? What does it look like for the threats on your team? What and being intentional of how we're evaluating this? Completing an exercise like this then can give you ideas for multiclassing and leveling up. looking at how you can cross trainin, how you can um create professional development plans for people. Maybe someone wants to get better at design, maybe someone wants to get better at uh using uh a various API.

36:53 You you hearing what people are interested in helps in giving people the ability to add to their classes or the roles that they can fill on a team as well as level up in their career. So, are there tools or resources available? Um, sometimes HR if you're at a bigger bigger company has access to like online courses that they can sign you up for at no cost. Um, are you both asking for feedback about how things are going as well as giving feedback about what's working and not work not working for you? Vocalizing interesting goals and advocating for your own career path are all pieces of this as well. And I think this also goes into if you are someone who is a manager, how are you advocating for those under you? Um, there is a st uh what's the word saying? We'll say saying in D and D that's don't split the party. You're in a dungeon. The tunnels uh merge away from each other and half the party says, "I want to go left." And

37:49 half the party says, "I want to go right." And you are all going to die because the monsters that are in those halves of the tunnels are not uh you are not capable of beating them if you are not a full team. Um so keeping the party together really this is about preventing siloing. It's about being aware of the monsters that or the quests that your teammates are on. It doesn't mean that you are necessarily fully engaged in their fight, but if they need that support, you're aware you can turn and, you know, cast the healing spell towards them or shoot the arrow at the monster they're facing while still accepting help that you need on that side. You are stronger together and can face much bigger things together than if you are siloed and working alone.

38:35 There's another uh piece of Dungeons and Dragons um where when all of a sudden you find yourself in a fight, how do you know how to take turns? Um you've got a bunch of people around the table. And the way that uh they sell for this is rolling initiative. Everybody rolls uh 20-sided dice and just based on those roles that determines the order. Um what that looks like here is is everyone getting equal play time? Is there the space in a meeting um in those check-ins, in those standups for anybody to speak up? Doesn't mean everyone has to, but is there that opportunity? Are you asking what do you think? Are you asking, "Hey, what are your ideas?" Are you asking a hey, any concerns like flags you want to raise on this? Are people aware of the knowledge that's in your head that they can then turn to you as a resource? Do people know what you know? Have you documented it or have you said something about it so they even

39:26 know to ask you those questions? and is your voice um being heard in the room as well and how are you standing up for that? Now, Dungeons and Dragons uh as we saw Vanessa's dice were not very kind to her in rolling high. Um and I think that that uh is hard to talk about um when we're living in everyday life. But the way that I've found it connects is in the conversation about competency versus capability. You may be fully competent at a skill and for whatever reason that day your dice just rolled low. So the barbarian trying to open the door, we know he's strong enough to open that door, but for some reason he's not capable right now.

40:10 So what does that look like on a dayto-day? You woke up late, your kid was screaming at you. The car had a flat tire. You just haven't had enough caffeine yet. What are the things that are debuffing you, if you want to call it that? or maybe it's just an off day, right? And recognizing that the capability that you have is not a statement on your core competency. You being really good at something is going to is going to show differently on a day-to-day basis. And so, it's really a statement on, hey, what are the things that you need to be aware of and not to get down on yourself or even the people around you? And just figure out what you need to do to call it roll again. what's the inspiration that you need to um get in there and try it again or uh recognize that hey today's not your day and I'll pick it up again tomorrow right so giving yourself the grace in that now finally when you're thinking about

41:07 the overall um skills that you have the skills that your team has one of the things that you then can assess is who's missing from the table what are the things that overall as a team scored right? The maybe in the self- assessments, you do realize that there's gaps. Um, so that can help influence hiring decisions. We all know what it's like to be on a team that's like, "Hey, we need to hire more people." And you try and hire the best fit. You put out, people submit resumes, you go through the candidates, and you're like, "Hey, this person seems awesome." But how are you assessing specifically and recognizing what your team needs beyond just another body to make hiring decisions that are as impactful as possible? Um recognizing where things are strong or weak on a team can in fact uh can impact mentorship. Getting people to hey I want you to go and meet with you know Alex once a month sit down talk

42:01 with him uh see what he can tell you about the projects he's working on or like maybe he can maybe you can shadow him or um just learning more. How are how can you use mentorship to help boost up those things that are weaker? Um, knowing and recognizing where your team has assessed that, hey, we're really strong here, but we are weaker here. That can be really impactful in advocating for what the project scope, timeline, and planning can look like. Saying, hey, we thought we could get this done in three months, but reality is we probably need five. That's the capacity our team is at based on this.

42:36 If you want it faster, then these are the things that we need to look for. Here's the things that we need to buff for. And then the idea of culture fit versus culture ad because we all want to work with people around us that we like, right? Culture fit is important. I'm not discounting that. But in that, how are we going beyond that to think about how someone is adding to the culture that's around us? thinking about the um the perspectives that they bring, the uh unique experiences that they've had, the uh resources or skills or tools that they bring in that are not accounted for, and how can they become an addition to and buff up the team uh in a way that these other options may not uh uh help out. So, what have you all learned today?

43:27 This is now open to the crowd. What did you all learn? That's the what? Oh, sorry. We'll pass the mic around.

43:44 Hello. Great. Um, I liked the piece that you were sharing about how it can be so powerful to do this kind of work in a team setting or in a group setting and to work on it on your own. You know, evaluate your own skill set. Um, but then also opening that up to the team to see where there are things that you're not seeing quite so clearly, but your counterparts can see like, no, I work with you pretty often and you absolutely should also be including this in your skill set. I think that's a really powerful takeaway for me.

44:20 Awesome. Anyone else want to He's gonna hand you the mic. the the skills assessment is pretty interesting because it makes you think about the positive things and focus on what you're good at.

44:38 Um, so that's a nice little perspective thing. Yeah, I I had never thought about the workplace as a dungeon before. That that's interesting. Although sometimes maybe you might think of your workplace as a dungeon. Uh what I thought was or maybe one thing that I learned uh is that we have individual quests that when we come together on a group quest like it it's kind of just a balancing act uh of trying to figure out the intersection of those two. Um because you talked about like splitting the party or not. Mh.

45:19 Uh, and part of splitting the party party or not is because, you know, we have individual quests and goals that we want. Uh, so I thought that was interesting.

45:27 Yeah, I just really loved your entire talk. I think it was it was great. Um, I've always thought about how the best teams are heterogeneous. They're not homogeneous. They're not all the same.

45:42 And I think your metaphor just really kind of drives it home. You know, you need you need to balance the party. you need a wizard and a paladin and a cleric and you need you need someone to tank damage and someone to uh you know find an exit route.

45:54 Um but yeah, I really love that and I I think that there was great value in looking at not just what you are strong at but what you're weak at

46:03 and how people on your team can help complement you and you can work together to complement your strengths and weaknesses to to become a better unit.

46:12 For sure. I really loved it. Thank you. So, I'm going to jump ahead to the now what because it's one thing to say, hey, this thank you for the compliment. It's one thing to say, hey, this talk was fun and I got to hear a talk about D and D and think about how it related to my team. But then it takes us into the so what or the now what of uh actually integrating it. And so, um I'm wondering if anyone has any now what. What would your thoughts about what's next after hearing this? And that's putting you all on the spot when you've only been hearing me speak for yeah 30 minutes. A little more. I'm over time. I'm sorry.

46:57 Sorry. Uh no, we're uh we're actively looking to add to the team and I think we'll go through uh some of these exercises. um we'll find one of these exercises to go through and and make sure that we're um adding folks that are going to make us a better party.

47:16 Awesome. So, go ahead. I think the age-old problem is like how long is it going to take? Carl

47:27 uh mentioned that it's an exact problem uh and it's how to fail is overestimating how long this thing's going to take. Uh and I definitely know almost all the teams I work on uh struggle right to say how many you know the company wants to know I want to spend this much money how long is it going to take and I love the base camp way of saying like what's your appetite I'll just get whatever I can get done in the time you want to spend

47:50 right that's that's kind of cutting corners uh to get it there I and my now what is figuring out how to work with my team so that we can better understand our delivery capabilities not based on capacity,

48:05 right? Because we use that word like, oh, how much capacity do you have? Oh, I don't feel like I'm that busy. Well, it's like what what does this act this task

48:13 actually require for these skill sets? So, better planning ahead of time, better understanding of the risks and the rabbit holes that are going into it. So then we can look at it and say as our team, we're super strong in this.

48:26 We can get this done really fast. But that one over there, maybe you should give it to a different team.

48:31 Yeah. If you want it done fast. otherwise give to us and we'll learn. Yeah. You know, but but without knowing all those things like I don't know that about my team members.

48:38 Sure. How do we do that? Yeah. And I think that figuring it out is going to vary based on your team and what your goals are because while this is a system that has been created, it may or may not be robust enough depending on what your outcomes are, right? And that's one thing that I want to make very clear is uh this is based on soft skills and actually planning out timeline and all of that is probably going to also involve looking at technical ability or um hard skills that you need to have assessed at a certain level to be able to make those projections. But yeah, so I hope that you move forward, find a way to inventory the skills around you on you uh for yourself and your team.

49:24 identify the monsters that you and your team may or may not be facing and continue to embark on your quest. So, uh, thank you all so much for having me. Um, again, my name is Chantel. Um, and I'm happy to answer any questions if there's still time for that.

Questions about this episode

What is discussed in "XO Ruby San Diego 2025 - Dungeons and Developers: Uniting Experience Levels... by Chantelle Isaacs"?

In order: 0:00 Dungeons and Dragons, Ascent, Chantel, Chantel Issacs; 5:00 Dungeons and Dragons, Dimension 20, Exor Ruby; 10:00 Dungeons and Dragons, Exor Ruby; 15:00 Dungeons and Dragons; 35:00 Dungeons and Dragons; 45:00 Chantel.

What is mentioned in this Confreaks episode?

8 people, works and ideas are mentioned, including Dungeons and Dragons, Chantel, Exor Ruby, Chantel Issacs, Learn Academy, Ascent. Each one on this page links to its own page with every episode that mentions it.

How long is "XO Ruby San Diego 2025 - Dungeons and Developers: Uniting Experience Levels... by Chantelle Isaacs"?

The episode runs 50 min; the transcript is about 9,031 words in 85 timestamped sections.

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