248: Developing Team Culture with Andrew Dunkman

September 1st, 2021 · 1 hr 12 mins

About this Episode

01:27 - Andrew’s Superpower: Stern Empathy

03:30 - Setting Work Boundaries

18:54 - Providing Support During a Pandemic

  • Stretching/Growth Work
  • Comfortable/Safety Work
  • Social Connection

23:37 - Keeping People Happy / Avoiding Team Burnout

36:26 - Developing Team Culture

  • “Gravity People”
  • Honing Communication Skills
  • Staying Ahead of Big Problems
  • The ACE Model of Leadership
    • Appreciation
    • Coaching
    • Evaluation
  • Learning Skills
    • Managers: Coaching How To Coach
    • Communities of Practice
    • Hiring External Consultants
    • Online Courses, Books, Podcasts

43:08 - Knowing When to Jump Ship and Understanding Your Skills

  • TKI Assessment
    • Competing
    • Collaborating
    • Compromising
    • Avoiding
    • Accommodating

46:51 - Developing & Enforcing Boundaries

  • Summarization
  • Normalization
  • Asking For Support

59:05 - Making Mistakes

  • Demonstrating Vulnerability
  • Acknowledge, Internalize, and Learn
  • Rebuilding Trust
  • Acceptance: Start Over – There’s Other Opportunities
  • Dubugging Your Brain by Casey Watts


Arty: The intersection between identifying and acknowledging creates the precedent for the norm.

Jacob: Evolving culture to enable vulnerability more.

Casey: Andrew’s river metaphor and Arty’s cardboard cutout metaphor.

Andrew: Talking about and building psychological safety is foundational. Going first as leadership or being first to follow.

How to start a movement | Derek Sivers (being the first follower TED Talk)

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ARTY: Hi, everyone. Welcome to Episode 248 of Greater Than Code. I'm Arty Starr and I'm here with my co-host, Jacob Stoebel.

JACOB: Hello! Nice to be here, and I'm here with my other co-host, Casey Watts.

CASEY: Hi, I'm Casey, and we're all here together with our guest today, Andrew Dunkman.

Andrew, he/him, is an engineering leader and software developer with 17 years of experience. He’s worked on and launched tools for contact relationship management, predictive sales, radiology and healthcare, learning and management, business-to-business timekeeping, and most recently in government at 18F, a part of the US General Services Administration that’s helping the federal government adopt user-centered technology approaches. He loves those.

He also likes building community in his free time. He helps moderate the DC Tech Slack, a 10,000-person community of tech workers in the DC area and he helps to run DC Code and Coffee, an informal hacking and community-building event every other weekend.

Even though his cat, Toulouse, is glaring at him for talking too loud, he is excited to be here with us today. Hi, Andrew!

ANDREW: Hey, y'all! So nice to be here. I'm honored to be a guest.

CASEY: Let's start with our standard question to kick stuff off here. Andrew, what's your superpower and how did you acquire it?

ANDREW: Thanks for asking. Yeah, this is whenever I answer the question of what my superpower is, it feels like bragging so I did what I normally do when I'm uncomfortable asking a question and I ask other people that question. I asked a few friends and they highlighted both, my ability to empathize with people and also, my sternness in that empathy.

I think sometimes when you get caught up in empathizing with people, you can allow their emotions and their feelings to overwhelm you, or become a part of you in a way that you're not necessarily hoping for. So I like to draw a firm boundary there and then allow other people to see that boundary, I suppose. [laughs] I don’t know, it's hard for me to say that that's a superpower, but I'm just going to lean into what other people told me.

ARTY: That's a pretty good superpower. I like it. How did you acquire it?

ANDREW: I credit my mom a lot actually. My mother is a dual major in psychology and English and as growing up, she had the worst way of punishing me, which is anytime I’d do something wrong, she would say, “Can you describe to me what you did and tell me how it made the other person feel?” which is the absolute worst thing to do to a child to make them explain how they've hurt you. [laughs] So I credit that a lot for developing those skills.

CASEY: That's so funny. You think it's the worst thing you can do? Could you imagine yourself doing it ever if you're around children like that?

ANDREW: Oh, totally. [laughs] Absolutely, yes. I now do it to my friend's children. I have no children myself, but I do to my friend's children and it's appropriately uncomfortable.

CASEY: I like that. Yeah. It can be the worst and it can be helpful and productive. I believe it.

ANDREW: Yes. As one of my coworkers like to say, “Two things can be true.”

JACOB: That boundary, I've been thinking about something along the lines of that recently, particularly in work settings where you can get really burnt out in everything is high stakes emotionally at work. I think that's a really good boundary to have.

ANDREW: Absolutely and it's also super hard to know. [chuckles] Both know where that boundary is and what to do when you are coming up to it. I think some people and myself occasionally notice you've crossed that boundary in retrospect, but not necessarily in the moment and it's hard to start off just know your tells when you're getting close to that line and when to pull the e-brake and take a walk, or go out and find some way to disengage, or reengage in yourself as a human and your human needs.

CASEY: I'd love to hear an example of a time when you pulled the e-brake recently, Andrew. It's so vivid you must have a lot of stuff under that sentence.

ANDREW: So my current organization, 18F, is one that's a matrixed so we’ve got our chapters is what we call them which is our disciplines. Those are engineering and design, product acquisitions, they're groups of people that do the same kind of work, and then our other angle of the matrix is our projects. Those are business verticals like the kinds of people that we're helping and the organizations that we’re assisting around public benefits, or around national security, or around natural resources.

So the result of a matrix organization is that you have two aspects to who's managing you—you have the manager of your work and you have the manager of your discipline—and the positive thing about that is that you can use both angles of the organization to support you in different ways. Sometimes in your work, you need someone to speak up for you as a person, or as your skills development angle and sometimes you need someone to speak up for you in terms of the project work that you're doing, advocating for success in the specifics of your project, regardless of the way you're contributing to that project.

The result, as you zoom out into upper layers of management, is that you have a conflict designed into the system and that conflict, when things are working well, benefits the health of the organization, both the health of people and the health of projects are advocated for and supported. But when things get out of balance, which happens all the time, in every organization I've ever been in you've got pendulum swing back and forth between different balances and when things out of balance, then suddenly you find yourself overextended, or advocating to an empty room.

A recent example was a conversation around advocating for the benefits of – I'm on the chapter side of the house so I support people within engineering and I had to pull an e-brake in a conversation where I was advocating for the health of people, but that I didn't have the right ears in the room to make a positive change. I found myself getting ahead of myself. One of the tells that I have is that I often feel tension in my jaw, which is usually a sign that I'm stressing too much about something. So I decided to take off a few hours and went to a gym [chuckles] and did a work out just to get the energy out of my system.

ARTY: It seems like those conflicts can become pretty emotional depending on the circumstances where you've got folks that are overworked and stressed out, and wanting an advocate to help support them in those challenging circumstances. You just think about product deadlines and things coming up and the company's trying to survive and it needs to survive so it can keep people employed.

Those things are important too, but then we've got these challenges with trying to live and be human and enjoy our lives and things become too stressful that we lose our ability to the function and we need advocates on various sides. So when you engage with someone, let's say, there's someone on the team that's burnt out and really stressed out, how would you approach empathizing with where they're coming from to help work toward some good the solution to these things?

ANDREW: Great question. I think in these kinds of situations, I always come in with the acknowledgement that no one in this conversation owns the truth. We're both working together to understand what the best thing to do is and what the reality of the situation is.

From my perspective, in trying to support someone seeing that they're burnt out, or overworked, that I think that's a misnomer. We can sometimes think of being burnt out overworked as an inherent state, or as something external. But I always try to encourage people to bring it internal because we all set boundaries and orders. The reality of an organization is that there will always be a resource constraint, whether that's people, or time, or money and it's up to the organization to effectively solve what they need to solve within the boundaries of those constraints.

So when people are feeling overworked, or when they're feeling burnt out, oftentimes there's an imbalance there where the organization perhaps is trying to achieve too much, or perhaps there aren't enough resources supplied here. If you can both internalize it to yourself and say, “Okay, it's up to me to set responsible boundaries so that I'm not burnt out, so that I'm not overworked and how do I, as a manager, support you in finding that boundary and helping push back when people try to violate your boundaries?”

Also, how do we, as an organization, understand where that line is and understand what kind of slack do we have? Because I think a lot of times in organizations, it's hard to see are we at 20% capacity, 200% capacity? It's hard to see because the more work you throw at people, unless you're getting pushback, it seems as if you still have more slack, more line you can pull.

Part of this is acknowledging that there is a systems level problem here where there's a lack of visibility into how overworked someone is and also, helping someone recognize hey, here's my boundary. We're over at. Now let's figure out a, how do we move that boundary back to where it needs to be so that I'm a positive contributor to this team and I can live my life [chuckles] in a happy way and also, how do we raise this in a way that the organization can see so that we can ultimately be more successful?”

If an organization is burning people out and making them feel overworked all the time, the work is not going to be successful. You care for people first and great people who are cared for then care for your projects and deliver great work.

JACOB: Yeah, and it’s like how can there'd be a health check for every person and what would that look like because I think if people are left to determine that for themselves, you can get really different conclusions from person.

ANDREW: That is a great question I don't know the answer to. [laughs] I've been thinking about this a lot recently.

My organization has a project health check where weekly, or bi-weekly, I can't remember, each project team talks about the different aspects of the work and whether, or not they're feeling well-supported, or if there are things external to the project that are getting in the way of project success. That gives you a data and interesting insights.

We also track our time and there is a way that we track our time that's flagged as support to the team. So that's where managers and people who are assisting in making big project decisions, those people track their time to that separate line. That's also interesting to look at because typically people ask for help after they already need it and the people that are close to the project can see that they need help. So if you're looking at the time tracking, usually a week, or two before something shows up on this project health tracker, you see a spike in hours in the kinds of support that people are providing to the project.

We have a lot of interesting data on the project health side of things, but it's really hard to collect data on the people part of this in a way that like makes people feel supported and it doesn't feel creepy. [chuckles] There's a whole aspect to this on whether, or not people feel comfortable reporting that they are feeling overworked and I haven't solved this problem. I'm curious if you all have ideas. [chuckles] I'd love to learn.

ARTY: One of the things I'm thinking about with burnout in particular is I don't think it's directly correlated to the volume of work you're doing. There's other aspects and dimensions of things that go into burnout.

So if I'm working on something that I'm really excited about, it can be difficult, it can be really challenging, it can be a huge amount of work, and yet as I work on it, as I get to the other side of that mountain I'm climbing, burnout isn't what I'm feeling like. It's a rush being able to accomplish something difficult and worthwhile as we don't necessarily burn out directly in correlation with working too many hours say, or something directly related to that.

The things I find that happen when people get burned out is when they lose their heart connection with what they're doing. When you love what you do, when you're excited about what you're working on, when you're engaged and connected to a sense of purpose with what you're doing, then we usually stay in a pretty good, healthy state. We’ve got to maintain not still keeping in someone in balance, but we're doing pretty okay.

Where I see developers usually burning out is there's some heart crushing aspect of things where people are disconnecting disengaging with what they're doing emotionally and they go into this mode of not caring anymore, not having those same compelling reasons to want to do those things and such that when that love connection dissipates, that work becomes too hard to maintain, to force yourself to do. So you start getting burnt out because you're forcing self yourself to do things that aren't an intrinsically motivated thing.

I feel like the types of things that we need to do are activities that encourage this sense of heart connection with our team, with our project, with our customers. We do need visibility into those things, but maybe conversations, or even just knowing that those things are important, making time to scheduling time to invest in those sorts of things. I'm curious your thoughts on that.

ANDREW: Yeah. Thank you for flagging that specifically. I think there's one thing that comes to mind for me is that is this work that you once loved that you no longer love? Like, is this something that you've connected with in the past and this really motivated you and now you're not motivated, I should say and if that's the case, what changed? I think brains are tricky and I think that we've all over the last pandemic, [chuckles] the current pandemic, I should say, the COVID pandemic is the one I'm referring to.

I think that as people have coped with lots of trauma in their lives and significant shifts and changes, it's come out in interesting ways. I think, especially as people are learning themselves a little more with new constraints, the impacts are not always directly connected between say, the project work that you're doing, maybe something that you once loved, and now suddenly you no longer feel attached to that. What is that? Is that the work is somehow different? Is it that you really just your threshold for everything else in your life is just ticking higher and higher and higher so now it's really hard to engage in any of the things that you once loved?

I personally have found myself, through the COVID pandemic, really finding meaning in repetition. So now I'm like a 560-day Duolingo streak and I've got podcasts I listen to every day of the week, and this repetition helps mark time in a way that makes me feel more like I have my life together. That gives me more capacity and reduces that stress threshold for me.

So I think trying to narrow in on what specifically changed and how do we tackle that problem head on, and it might not be the work, or connection to the work.

The other side of the question is, is this work your love? Maybe this is work that they've never really loved. Maybe this is grunt work—and one thing that I like to acknowledge is that every project has a grunt work associated with it and if you don't really have a framework for rotating that grunt work, a lot of times it falls to the person who has the least privilege on the team.

So if as a positive team, you can work together and say, “Hey, these are the set of tasks that just needs to get done,” maybe that's notetaking in meetings, maybe that's sending out weekly status emails, or running a particular meeting. “Let's rotate that around so that we can find a balance between the grunt work and then the work that we're here to do this stuff that motivates us.”

Because if the grunt work doesn't get done, the project won't be successful, but also, we all really want to work on the other thing, too. So let's make sure that no one here gets shafted with all that work [chuckles] and I think especially if teams haven't deliberately thought about that, patterns start to emerge in which people with less privilege get shafted. So I think that's something to be well acknowledge.

JACOB: Quick shoutout. Episode 162 of this podcast, we talked with Denise Yu who really is framing exactly what you're talking about. She calls it glue work and it's that work that's maybe not directly recognized as a value add, but is the work that holds all of it together. So all of the work that might get done in JIRA, or around a Wiki, or organizing meetings, taking notes, all the above.

The basic theory is like you said, how can that glue work be distributed equitably? Not to say that certain roles don't intrinsically need to do certain types of glue work because that's what their expertise is in. But it was a really good conversation. So if people are interested, go check that out, too.

ANDREW: What are some ways that you're seeing that pandemic affect people in their work?

ANDREW: I think the answer to that question is as varied as the number of people [laughs] that I support. I think each person is affected in dramatically different ways, which I didn't quite expect, but taking a step back and thinking about it, of course, each person's individual and each person reacts differently.

But I would say that for some people, especially people in care-taking roles, that kind of work has to shift to support them. So if you're someone caretaking, you're often dealing with a lot of details in your out of work life and especially through the pandemic, now those lives are merging together.

I'm currently at a remote organization and have been at a remote organization for the last 10 years, or so. The remote work thing is not necessarily new, but the complete merging of all of the things life and work is something that's still new and I think a lot of people who work remotely regularly often find ways to get out and get more exposure to people in their personal time, which is also something that has been limited. Especially if you're caretaking, you likely are doing that even less of your threshold for getting out is even lower.

So if you're constantly dealing with details in your life, it might be good for you to take on more of that glue work, or more of the when you're thinking about the – I think I've worked in three categories.

You've got the stretching work, or your growth work and that's work that is right on the cusp of your understanding. You're not really good at it yet, but by failing and by having moderate success, you grow as an individual.

There's also your comfortable work, or your safety work and that's work that you're good at, you can knock it out of the park, do it really fast. I think for folks who are dealing with a lot in their personal life at the moment, leaning more towards the glue work, more towards the safety work is really important for making you feel successful and you're not really hungering that growth. I wished I remember the reference, but I heard someone referring to growth as being in a boat in a river before. Sometimes the river is wide and sometimes the river is narrow. When the river is wide, you really need to row.

I found myself personally, in the last couple of years, not necessarily needing to grow as much and the river feels more narrow to me. So the current is faster and you're taken away with growth and you don't really need to do a lot to get there. Instead, you need to hold on [laughs] and try not to capsize. So that's one aspect, I would say I've seen people…

CASEY: That's such a cool metaphor. I'm going to remember that.

ANDREW: Yeah. I wish I remembered where I heard it from so that I can reference it for you all. It's definitely not an original idea of mine.

But another aspect of the way people have individually in coping and needing support is around their social connection and that's an easy example. I think we've all felt differences in our social connection through COVID and sometimes that takes the form of having more structured meetings.

Some people find more structure gives them the ability to communicate with each other in a way that makes you feel social and also isn't as draining and other people are the exact opposite where they want to get together in a room with less structure so that you can all just hang out and the structure gives people a sense of feeling stressed.

The way that I've been looking across my organization is what kind of things are we providing and are they varied enough that we're capturing the majority of people in the support that they need?

CASEY: I thought about a lot in the dance communities I am in that there is a lot of introverts that love to go dancing, partner dancing, because it's structured and they'll say so. Like, I love that I can just show up and do the thing and it's social, but I haven't thought about the other side of that, which you just said, which is some people don't want the structure. I'm sure those people exist and I just probably know a lot of them, but I haven't heard people say that about themselves as much. The introverts in the dance communities know and they say it. The other side, I'm going to look out for it. That's cool.

ANDREW: I used to play music for religious music ministry and one of the rules we had is that if you're always picking things you like, you're leaving people out. I think of that not necessarily attached to music ministry, but attached to all the other work that I do and that’s if your preferences are always represented, someone else's preferences are not. So trying to look around and say, “Who's not in the room right now, who could be benefiting from having their preferences heard once in a while?”

CASEY: I want to jump back to how can we tell if people are about to be burnt out at work? How can we help people have a healthier environment?

One of the lenses that I think about all the time is Project Aristotle by Google that came out, I don't know, maybe 5 years ago at this point and we're mentioning a lot of that aspects of it in our conversation already. Earlier, we were talking about on their list four and five are meaning of work like personal importance and impact of work, which is the company mission a little bit more. The other three that we touched on a little bit but not as much is psychological safety, which is number one on their list, dependability, like depending on each other, the coworkers, and structure and clarity, like goals, roles, and execution.

I'm sure this is not a full list of what keeps individual employees happy. But I think a team environment that hits all of these five really well is going to have less burnout. More than individually, it's been studied. That's true.

So when I did team health surveys before for the team, for the people, I like these five questions a lot. I bet it's a lot like the project surveys, Andrew, you were talking about. A lot of team health surveys are similar, but you got me thinking now what's missing from that list that's focused on the team that would show up in the individual one and I don't have a clear answer for that.

ANDREW: And adding onto that, is there a way where you can collect honest data? I think one of the benefits of having one-on-one relationships with your immediate manager is that they can read between the lines and what you're saying after they get to know you well enough.

I think for me, that usually happens about a year in with a new employee where you get to know someone well enough that you can understand. If they come to you and say, “Hey, I'm struggling with this right now in this project.” Is that a huge red flag, or is that normal? I think it takes a while to get to know someone and then you can read between the lines of what they're saying and say, “Okay, this is a big deal. It deserves my attention. I'm going to focus on this.”

One of the things I struggle with capturing this information is that a, it's hard to capture that sort of interpretation part in these kinds of surveys and b, the data that you get is – when we were talking about burnout a lot, sometimes when people are burned out, they don't have the energy to submit these surveys. [chuckles] So the data is not particularly representative, but that's a hard thing to keep track of because how do you know? So it's a really tricky problem. I'm going to continue to try things [chuckles] to get this data, but I do like the idea of looking between the lines on if we're surveying team health, is there a way we can focus in on individuals?

ARTY: There's also a lot of things that we don't talk about. Like Casey brought up psychological safety, for example and if you don't feel safe, you're not likely to necessarily bring up the reasons that you don't feel safe because you don't feel safe. [chuckles]

I'm thinking about just some team dynamics of some teams I've worked on in the past where we had someone on the team that had a strong personality, and we would do code reviews and things, and some folks that were maybe more junior on the team felt sensitive and maybe attacked by certain things. But the response was to shut down and fall in line with things and not rock the boat and you ask him what's going on and everything's fine.

So there's dynamics of not having psychological safety, but you might not necessarily get at those by talking to folks. Yet, if you're sitting in the room and you know the people and see the interactions taking place, you see how they respond to one another in context. Because I'm thinking about where those dynamics were visible and at the time, the case I'm thinking of was before the days where we were doing pull requests and stuff, where we did our code reviews in a room throwing code up on the screen and would talk through things that way.

You'd see these dynamics occur when someone would make a comment and how another human would just respond to that person and you see people turn in words on themselves. These sorts of just dynamics of interaction where people’s confidence gets shut down, or someone else is super smart and so they won't challenge them because well, they're a super smart person so obviously, they know. Some people speak in a certain way that exudes confidence, even if they're not necessarily confident about their idea, they just present in a certain way and other people react to that.

So you see these sorts of dynamics in teams that come up all the time that are the silent undercurrents of how we all manage to get along with one another and keep things flowing okay.

How do we create an environment and encourage an environment where people feel safer to talk about these things?

ANDREW: To me, psychological safety and inclusion are very closely tied and I believe that inclusion is everyone's responsibility on a team and in the situation you described there, who else was in that room and why didn't they stop it? I think that it's easy to say, “Oh, these two people are having a disagreement here,” but if we all truly believe that it's our responsibility to create a safe environment and include everyone and their ideas. As you mentioned, everyone in that room could see what was happening. [chuckles]

So I think there's a cultural thing there that perhaps needs some work as an organization and I'm not saying that that is something that I don't experience in my teams as well. I think this is work that's constant and continual. Every time you notice something, it's to bring it up and invite someone back into the conversation.

Some people like to think about calling out, or versus calling in and I really like that distinction. When someone oversteps a boundary, or makes a mistake, they've removed themselves from this safe community, and it's up to you as a safe community to invite them back in and let them know their expectations and I like the idea of that aspect of calling people in.

Obviously, that requires some confidence and I encourage people, especially people that have institutional privilege, to especially looking out for this because you can really demonstrate to your team how much you're willing to support them if you keep an eye out for these kinds of dynamics.

One thing you mentioned really made me think about earned dogmatism. When people are around for a longer time, they become more closed-minded. That's the earned dogmatism effect and it's the idea that since you've been here for so long, or since you've been working in this industry so long, you're the expert and it causes you to become more and more closed-minded to new ideas, which obviously is not good. [laughs]

So anytime I see that pattern popping up, I try to just let people know like, “Hey, do you know about this effect? Do you know that this happens with people in teams and is that how you would like to be? Would you like to become more close-minded, or would you like to continue learning?” I think just the awareness of the fact that that's something that you're going to inherently start doing helps people fight against that.

JACOB: I'm trying to imagine just a typical, if you can call it that, team in a tech company and they're probably in a state where a lot of these things we're talking about might not come so easy because I think what we're saying is that a lot of this is dependent on everyone on the team being vulnerable about where they're at.

I wonder if you have any ideas about how a team can get from there to the ideal state because it sounds like that's a really big barrier. I can't have better psychological safety and inclusion without somehow getting people's feedback and I can get feedback if they don't feel safe. So is there some iterative way to improve on that?

ANDREW: Yeah. So one thing that I have direct experience with is in the federal government, there's a lot of funding models between the federal government and local governments where the federal government will pay for a majority of something as long as the local government follows a set of rules on implementing a program. So like Medicare and Medicaid are examples of this and other benefits programs as well. Even the federal highway system; the reason why our interstates are all the same is because the federal government pays for a majority of them if the local authorities building roads follows a set of rules and guidelines.

I think that's one of the most dramatic examples of a power difference. If you're forming a joint team to make changes to Medicare, or build a new highway, or improve rail service in your city and one person in the room controls 90% of the money. I think that's a pretty dramatic example of what could be a really psychologically unsafe environment and it requires a lot of effort to break down that boundary of, “Hey, I'm here to say yes to what you want.”

But then the reality is the federal government representatives in those situations are often looking to collaborate and help solve problems because they're looking out to see how do I best spend this money to achieve the best effect. But the tendency is that other members of the team coming from the 10% side of the house, they're responsible for the execution of the program and so, they tend to hide mistakes, or hide hiccups as much as possible so that they don't get their funding cut.

That's just a very natural thing that happens and the experience that I have in this situation is what I like to think of as the Waffle House solution. I heard of a particular person in this situation taking the whole team to Waffle House. This obviously works better in-person. It's hard to take people to Waffle House remotely; that's definitely not something that you can't do.

The idea behind that conversation is just the problem here is that you're not connecting with each other on a human level and you want to be safe to share your vulnerability with each other, but before you can be vulnerable with each other, you have to recognize each other's humanity and let everyone know that you respect each other.

I think an easy way to do that is to share a meal, maybe it's to play a game together, maybe it's to schedule a meeting for 30 minutes in which you talk about note work. In the example that I gave it's up to the person in the position of power here to set that example, because if you're someone without that privilege, if you are someone who pays for 10% of a project instead of 90%, it's hard for you to go to your 90% funder and say, “Can I waste 30 minutes of your time? Can I waste half a day?” Because waste in this case is the idea from the business side of the house. You're wasting time.

But in reality, if you slow down and connect with each other on a human level—slow is smooth and smooth is fast—so you can help the team develop that sense of humanity with each other, create an environment where hopefully you can be more vulnerable with each other and collaborate more humanly with each other.

So I wouldn't necessarily say that this is a textbook plan like okay, you've got problems on your team, let's go to Waffle House and the problem solves. [chuckles] I'm not saying that but I am saying perhaps look for opportunities for you to recognize each other's humanity, and break down perhaps a structure that might be standing in the way of connecting with each other, and then just focusing on that can hopefully help you find that vulnerability better.

JACOB: You can't take yourself seriously at a Waffle House. It's just not possible.

ANDREW: [laughs] I'm pretty serious about Waffle House. I don’t know about you. [laughs]

CASEY: I'm starting to get a craving here.

Yeah, totally agree. I love that this is being talked about more and more, how do we build psychological safety on teams? It comes from trust, human connection, vulnerability, and how do we build that? By treating each other as humans.

ARTY: The things I think about just contrasting some teams I've seen over time and how they ended up developing and the culture that emerged is the technical leadership on the team that organically evolves. Some people have strong personalities. They tend to naturally act in a leader-oriented way. Even if they don't officially have the title hat on their head, they're somebody that people respect and look up to. They value their opinion and thoughts and whoever those people are that have the natural gravity tend to have a lot of influence over the emergent culture.

So when I've seen people in that position, be really supportive of listening to the ideas of other folks on the team, creating space and treating people with respect, creating an environment where people are heard and listened to and it's about the ideas that the behavior of those people have an outsized impact on the culture that emerges by just how they interact and treat you respect others and other folks on the team tend to mimic and model that behavior of wherever that natural kind of gravity is going toward.

If you've got folks on the team that are like that, that have a tendency to lift up other people around them, then what emerges is a much more psychologically safe environment. When you've got somebody in that gravity position that has an ego defensive response, they want to continue to feel like the confident expert ones, when people say counter things that are positioned as a challenge and you get a very different set of dynamics that emerge where people tend to be more walk on eggshells, try to say things very carefully to not upset things.

I feel like it's just human instinct response depending on who's in the room, who you're talking to, how you anticipate they will react to something, that emergent interactions come from that and that whoever those gravity people are tend to have this outsize influence. So who you have in your organization of those folks? I'd say probably being really careful to hire people that have a tendency to and a desire to want to lift other people up and to maybe not have such a fragile competitive ego dynamic going on.

ANDREW: Absolutely. Well, I have lots of feelings on hiring, [chuckles] but I do think that in the tech industry, we don't spend as much time focusing on communication and then I think that we should. I think a lot of times people who are in that ego situation are expressing vulnerability, but poorly and I think if they had more communication skills, they could potentially express that differently in a way that was more positive to culture.

So zooming back to one of the things you said around leadership, evolution, evolutionary culture, and who steps into leadership roles, I think one of the things that is really important to me about good leadership is staying ahead of what your big problems are and that isn't necessarily saying working ahead of everyone else. That’s saying keeping your eye on the horizon. Like, are you looking out to where we're going and what kind of problems are we seeing here?

If there's an acknowledgement of an issue with psychological safety on teams, letting leaders emerge naturally may not be the right approach. You can deliberately select someone who demonstrates the culture that you want to create on a team has that technical leader and give them –

I like the ACE model, the appreciation, the coaching, and the evaluation of leadership, where you give them that appreciation on the particular things that they're doing really well and in front of the team so that the team can say, “Oh, that's what the norm is here. That's what we should be doing.”

That also gives the person, who may have perhaps more of a natural leadership role, if that would have naturally emerged, but perhaps it's missing some of those communication skills, or other skills that makes them a more around teammate, gives them an opportunity to be out of the spotlight so that they can work on developing those skills and becoming a more active contributor to the team instead of holding it back in some ways.

CASEY: I love that we keep saying the word “skill: because these are all learnable skills. You can learn how to communicate well. You can learn how to be a strong, effective leader. You can learn how to foster a psychologically safe and inclusive environment. You can learn all these things.

I love to work at places where they want this, the culture that the leaders, the people who run the company, want it even if they don't know how yet because that growth is possible as long as there's the desire for that. I think we all have a base level of desire, but some people are aware of it and articulate it and say – I saw a tweet the other day. Someone was looking for a job and of their five criteria, top five they listed in the tweet, psychological safety was on the list. That person knows they want to work on a team like that. That's pretty cool.

So someone wants their team to learn these skills. A natural way is managers coaching their employees to do that kind of thing like coaching how to coach. That can work pretty well. It's pretty powerful.

Another one is communities of practice, where you have people come together and talk. It could even literally be about culture. Some companies have a culture, community of practice, where they talk about how to influence the culture. Some places don't have the skills yet and they hire external coaches. There's a whole bunch of companies including me. For myself, I'm a consultant for making happy teams. I do coaching and training, too. There's online courses, there's books, there's podcasts like Greater Than Code. It's pretty good. You should check it out. [chuckles]

But acknowledging the problem, being aware of it is a huge key first step and I don't like to push for a psychological safety in a place that doesn't value it. That's just a recipe for burnout for me. It's happened to me a lot, but in an environment where it is already desired, getting people from wanting to, to being able to. That’s super satisfying work. I think that's true for anyone in tech who is talking about this kind of stuff, who cares about it. You want to make a difference where you can.

ANDREW: Absolutely knowing when to jump ship at an organization because you are fighting upstream at a time when you are either being taken away in the current, or there aren't enough other people around you to swim upstream with you, it is super important.

One of the things that helped me open a door in my life that I'd be happy to share with you all is an assessment I took a couple of years back called the TKI assessment, Thomas Kincaid Institute assessment, or something. I could've gotten that all wrong, but it's a tool that helps you understand what skills you already have around conflict resolution and what skills you can grow around conflict resolution.

That unlocked a lot in my life specifically because it allowed me to understand how I naturally resolve conflict, to understand when I should push against my natural instincts to resolve conflict, and when I should feel that I have exhausted my abilities to resolve this conflict. That last step is a great indicator if you've tried everything you can to resolve the conflict, and maybe that conflict is around creating a psychologically safe workspace, you yourself cannot do this. So can you bring in other people that can help resolve this, or is it time to walk away and find a team that supports you better?

The five different modes that they reference in TKI are competing, collaborative, collaborating, I should say, compromising, avoiding, and accommodating. When I first took the assessment, I scored a 0 in competing which means I had no recognizable skill in competing. When I look back into my history, my childhood, how I was raised, that totally makes sense. I was raised in a household where when people wronged you, you let it go. You moved on to find people who would support you and believed that that person would eventually experience justice and that was not your responsibility to do that.

Applying to my work-life today, that means people can walk over me. [laughs] So how do you pick up those skills? The assessment doesn't necessarily dive too much into how you pick up the skills, but I think just knowing where your blind spots are was really helpful for me, because then I could recognize a situation where a, I flagged that I'm experiencing conflict. B, my natural tendency is to accommodate this conflict, or avoid it. C, is that the right approach for this environment? Is that a right approach for this problem? And then d, either do that approach, or change it.

It's really uncomfortable. Often, when I'm competing, it makes me feel selfish and I acknowledge that. So when I'm like, “Okay, I'm going to change my approach and I'm going to compete here. I'm going to argue.” It's like, “Okay, I'm readying myself,” like, “Okay, I'm going to feel selfish now, be ready to feel selfish, go for it.” [laughs] And that's just sort of how I counteract those natural tendencies.

So I wouldn't say there's one particular magic bullet, or this is the assessment that you should do, or anything like that, but there are a number of tools out there to sort of help you understand yourself and what skills you have and what skills you might want to grow into. They can also provide a sense of completeness around a particular skill area, like conflict avoidance, or conflict resolution, and let you know when you've exhausted the available options in front of you.

ARTY: That's interesting to me just thinking about where we started this discussion with boundaries and just people can react in a different way, and if you have someone who's kind of overstepping boundaries, how do you learn to stand up for yourself? If your instinct is to just run away from conflict, whenever it comes up, then we've got other sorts of problems and stuff that emerges. Sometimes, the right thing to do is to stand up for yourself and to be able to have the confidence to feel like you can.

One of the things that that helps me with that is when someone else is upset and reacting and stuff is maybe they're attacking me, or something is to separate myself personally for that. So if I imagine them in their head and I'm a cardboard cutout character that I'm like, “Okay, they're kicking the cardboard character and that's not me.” They have a picture in their head of this little cardboard character that they've got an upset relationship with that that's separate from me.

I can look at the dynamics that are of what's going on with them and why they're upset with this cardboard character, understand what's going on in their world with separating myself from that, and then I can respond in a way that is standing up for myself without necessarily reacting to the situation where I feel like I need to defend myself against an attack that something going on that really has nothing to do with me, but still, I need to be able to stand up for myself and not necessarily back away from the situation. So I find those kinds of skills really help with being able to not take other people's stuff so personally.

You talked about the challenge with boundaries and over empathizing can put us in a situation where the things that other people say can end up hurting us a lot, or we internalize somebody else's feeling so much, or someone else's worldview so much that we can lose ourselves in someone else's emotions and feels. How do we separate enough so that we can have a solidity in our own self and our own sense of knowing such that we can have our own compass that doesn't fall over, that we can feel bolstered in ourselves, independent of what everyone else is doing? That's where that empathy and boundaries and resilience and stuff come in.

So a question for you, you did mention this boundary thing early on, what are some of the things that have helped you to develop boundaries, or some of the tools that you use to help in those challenging situations?

ANDREW: I love the cardboard cutout analogy. I personally like to replay situations as if they're soap operas. I'll describe the characters, especially when things get heated emotionally, it's easy for me to recognize it as a soap opera, which helps me chuckle about the emotional component of it in a way that externalizes it from my feelings.

It's a really tough situation. That's a tough ask. I think one thing that I do in the exact moments when I am feeling hurt, or valued, or some kind of emotional component is attached to something someone just told me is to again, pull that e-brake and say, “Okay, stop. I am not my work.” Similar to when you submit a pull request, you are not your code. I am not my work. I am not this conversation. I'm a whole self, I am valued as myself. I'm surprised by something that just happened and I'm reacting to it in a particular emotion, emotional reaction.

So if you can create a pattern, when people get you into that emotional state, whether, or not they were intending on getting you there, of saying, “Hold on, I'm caught off guard by that. Can you tell me more?” Like, “I don't understand that comment.” It shifts the power dynamic from someone putting you on the spot, which they may, or may not have intended to do, to shift it back towards them to say, “Now the responsibility is on you as the person who has made me feel upset, or I'm caught off guard by that and the responsibility now is on you to describe more so that I can contextualize the emotion that I'm feeling, or just give me time to react to that.”

You don't always have to immediately respond and oftentimes, I find myself reacting too quickly. All of the tools that I have in my toolbox are slowing down. That's one of the tools that I definitely use to help acknowledge that something is unusual.

Another tool is I'm asking people to summarize so acknowledging that, “Hey, I'm surprised by that and I'm starting to get lost in the details of this meeting. Would it be all right if I asked you to summarize the main points here, or could you follow-up in Slack after this, or follow-up an email after this?” That's another one of those, like my natural tendency to avoid. It's like okay, I can take a step back here and avoid this immediate conflict, or this immediate emotion, and then take a breather.

Often, in the before times, as I would go out and speak at conferences and I'm not a natural extrovert. I have this tendency after I speak at a place to go find a closet, or some dark room somewhere [chuckles] just to recharge a little bit, do nothing. I often will just sit there and sweat in a closet for 30 minutes, or something like that. That process allows me to reset my blood chemistry and say, “Okay, how do I fully acknowledge this situation?” Like, do I feel like I did a good job? Am I proud of the work that I'm doing? Am I proud of this? Is this where my boundaries should be? It allows me to give that moment to step away, to reset a little bit.

So it’s something I think that I will spend the rest of my life learning, which is how to recognize my boundaries and set them appropriately, and I think that's right. I should be continuing to learn as I continue to change.

ARTY: I really liked the summary thing. Just thinking about someone's really upset, it's a pretty safe question to ask and at the same time, it forces them to take a step back and really think about what it is that they're trying to say. Because usually when we're upset, we just spew lots of words of upsetness, but it forces you to shift into more of a thinking mode away from emotional mode, which I feel like would have a really good impact on level setting the conversation. Just take a deep breath. What is it you're trying to communicate here? What are the main points? I really liked that summarization idea.

ANDREW: The one thing I always myself in those moments is, “Nothing is more important than my next breath,” and that helps me to unplug from the situation and focus on breathing and focus on relaxing and then be able to show back up and reengage.

JACOB: Something that I think can be important is if I'm at work and I'm realizing that I need to be vulnerable in one way, or another because I need to draw a boundary, or for some other reasons, something that I feel like would be really important that I would really need to have is an example that would give me some idea of what will happen when I do that.

How can team members get examples of what happens when I'm vulnerable, because if they don't know what will happen, they're probably going to be left to their own personal experiences from maybe at another job, or something like that, that probably don't apply, that probably would be completely different. So it's like, how can managers, or leaders help people see, or experience examples of this is how we talk about difficult conversations to normalize it and just help people understand, like, this is what will happen and this is the way we go about it and yes, it will be safe.

ANDREW: I don't think you can say that. [laughs]

JACOB: I know.

ANDREW: And that maybe is controversial, but I don't think you can say, “Yes, this will be safe.” I think you can strive for it and you can work for an environment that's safe, but in a professional setting, there's always a line and maybe it's not safe to share something that you think is appropriate to share and there are lots of reasons for that. Maybe it's the impact on other people.

But the pattern I like to encourage and people just ask for permission, which is something that is maybe not always universally applicable advice, but oftentimes, I find myself talking to people when they're on teams where they want to say something controversial, or they want to say something difficult, or they want to share something that's personal and how they attach to this project, or this work, or something that happened in the team.

I think there's a lot of power in asking people to support you to coming in and saying, “I really want to share something with you all and I'm not sure how it's going to go. Can you support me in this? What are you interested in hearing?”

The way I often say it, when I'm trying to say something controversially is, “Can I be spicy for a moment?” [laughs] And that's an acknowledgement of saying like, “Hey, I'm going to say something comfortable.” It gives people a moment to set their expectations and it gives them a moment to recognize how they should respond before they hear what you say and then are caught up in the emotion of the response.

I think that's a really kind thing you can do to your team to say like, “Hey, can I be vulnerable for a second here?” Like, “This is a project which involves researching prison populations and three of my family members are in prison.” If you lead off with saying, “Three of my family members are in prison,” people don't know how to understand that comment. But if you start by saying, “Can I be vulnerable for a second?” People will recognize that hey, you're showing something deep about you and your personality and it's something tied to your sense of identity, or something deep within you in a way that is not the responsibility of the team to validate, or say it's right, or wrong.

But it is the responsibility to the team to hear you and to understand you and ask questions to say, “Hey, tell me more about that. Tell me more about how that connects to this work,” or “Do you want to interview some of your family for research on this project?” [chuckles] Or “Do you want them to stay out of this project?” Or “How do we support you as a team member? Is this something that you want to acknowledge, but you'd prefer to put that in a box and keep it on the shelf, or is that a part of your identity that you'd like to bring to this conversation and bring to this work?”

I think those conversations like can really benefit from that asking for permission step and you don't really need to wait for people's answers there, [chuckles] but it gives you an opportunity to set the tone for the conversation.

JACOB: I feel like if I was working on your team and I saw Andrew use that phrase, “Can I have permission to be vulnerable? Can I be spicy?” I feel like later when I felt like I needed to be vulnerable, I would feel a lot more comfortable because now here's a map that's if I do this, it's probably not completely out of bounds and that now I have a way to know here’s how we go about that on this team, because there’s a leader who modeled it.

ARTY: Yeah, bingo. I was just thinking about all the different ways I've screwed things up and stuff and learned, I guess, the hard way, what boundaries are the hard way of what unsafe things are is by making mistakes and screwing things up. I think about some of these experiences that I had and I feel like the saving grace for me, even when I messed something up, is that I genuinely cared and that people knew that and could see that and so, that when I apologize for something, it was authentic and that we could move forward and stuff because I cared. Underneath it all, I genuinely care. So even though I made some mistakes and stuck with things that was okay.

And then after that, when I was thinking about being in more of a leadership position, one of the things I made a point of doing was putting mistakes and stuff I've made on center stage. Making it okay and safe for people to talk about when they screwed something up. Being in a leadership position, when I talked about all the things that “Well, I screwed up this thing, I screwed up this thing;” it makes it okay when our leaders demonstrate vulnerability, or create ways and pathways that show us how to do those things safely, too.

ANDREW: That reminds me of a friend of mine had a conversation with me last weekend specifically around a mistake that they had made and that mistake was in an online community. They were discussing building a world in a video game and they suggested building something that was offensive. They immediately dove into how they didn't know it was offensive at the time and that the reaction that other people gave to them was inappropriate and that they felt like they didn't know how to apologize in a way that would help support growth, or reengagement with the community, and that they felt like, “Maybe I'm just being canceled,” or maybe people are overreacting here.

After the whole conversation, I just let them talk out and they ended with like, “How do I reengage here when people are now ignoring me?” and I just said, “Well, you don't deserve a second chance.” Not that anyone deserves to be canceled immediately, or cut out, but when someone says something offensive that you take offense in, it's up to that person how much tolerance they have for you. If someone has decided that this in this situation was so offensive, or that their tolerance for that offense is low, you don't get a second chance there. That's a mistake that becomes part of you and hopefully, you can allow that burden to not rest on your shoulders and hold you down, but you can internalize it and learn from it, and it becomes part of the foundation you stand on so that you don't make these kinds of mistakes next time.

And also, [chuckles] demonstrating an aspect of my superpower, I disagree with you. I don't think you didn't know that that was offensive. [chuckles] I think you had that part of your brain turned off and hey, can we like talk about that? I think that this particular thing, you knew it was offensive, but you were thinking about this in a different context, or you thought this would be okay, and now you're rewriting this and placing yourself as a victim. That is a dangerous pattern so don't do that. [chuckles]

I think that in a work setting, tying this back, when you are having these difficult, or vulnerable conversations, being able to acknowledge when you've made a mistake, maybe perhaps when you've shared something that is offensive, or perhaps you've made a comment about someone else's moment that's offensive, it's really important to acknowledge the mistake to provide the opportunity for others to give your feedback and acknowledge that you've damaged trust here.

It's your responsibility as the person who damaged that trust to then rebuild it and maybe rebuilding that trust means leaving the organization, or changing teams, or maybe that means really, truly deeply listening and empathizing with people moving into that position of hurt that you've caused and being uncomfortable with it, especially when you're personally wrong.

When I'm personally wrong, I really feel that I want people to understand how much I'm hurt and if there isn't a great opportunity to share that pain with someone it's hard to accept their apology, because you don't feel like they understand. In those situations, it's up to the person who's done the controversial thing, or overstepped that boundary to step in and say, “Let's talk about this when you're ready.”

ARTY: And also, the other thing I'm just thinking is that when things do happen, we need opportunities and stuff to start over, too. Sometimes the right thing to do is walk away from the whole thing, but learn from it and there's always, there's so many people out there, there's so many opportunities out there, and we're surfing on the waves of life. We learn things along the way and there's always new relationships and things we can build and if we take those lessons and stuff with us for when we do screw things up that maybe we can navigate the next opportunity a little bit different.

I've had enough facepalm moments and stuff of just relationships where the things that come to mind for me are things where someone was put off from me because I'm kind of the passionate, excited person and not everyone knows how to deal with that, or might think I'm a weirdo, or something. So I'll scare someone away and I don't mean to. I'm like, “But I'm a nice person” kind of thing, but sometimes there's nothing you can do about it.

It's like this first impression thing that you can never really fix, but there's other opportunities out there, there's other relationships, and maybe the purpose of this interaction in your life is just for you to internalize and learn this lesson so that you carry it with you forward. We're all surfing on the waves of life and these kinds of things happen and it's not the end. It's just an opportunity. It's an opportunity to learn a lesson that then we can take with us into the future.

ANDREW: Absolutely. Yeah, I know. I've been fired from jobs, had friends cut me out of their lives and made a lot of mistakes. That becomes part of who I am and I carry that forward and I'm happy that I've made these mistakes in my past because they prepared me for making bigger mistakes in the future. What could be more fun?

CASEY: A lot of people get stuck on these experiences, thinking about them over and over and over in a loop and one way to get out of the loop is to correct the situation, which people like to try first, of course. Like, try to get back into that relationship, or community. Another way is to realize there's nothing you can do and move on, that's often called acceptance in meditation mindfulness terms. But it can be hard to get to acceptance if you feel like there's something you can do still, or something you could learn, you didn't learn everything you could yet and how to do that is hard.

It's a lot of the chapters in the book I wrote, Debugging Your Brains. I'm not going to go into that right now, but there are things you can do to get out of the loop when you're stuck in the loop. I feel so awkward ever plugging my own stuff, but it's so relevant. That's what we're talking about here.


Y'all don't mind, I know.

JACOB: No, I'm glad to hear about it.

CASEY: Now let's go to reflections. So at this is the part of the episode where we each reflect on something that stuck out to us. Something we'll take with us. Something that was interesting from today's episode.

ARTY: One of the things that stood out to me as we were talking about psychological safety, and these dynamics of leadership and who we choose as leaders as being important is this intersection between once we identify what the kinds of things are that we want to select for, that we can identify those people and then give them acknowledgement, the baton of an official hat to wear, and what the effect of that is, is a way to say to the organization of, “Oh, these are the normal things that we want to build around those characteristics.”

So there's this intersection between identifying those things and acknowledging that with – I'm holding up a little ball right now, give someone that baton, the thing, or whatever and that the combination of those two things is what creates the precedent for what is the normal we're trying to move towards. So it's not just the hiring, it's not just management things that we do; it’s the intersection of those two things that sets the norm.

JACOB: I'm thinking a lot about a possibility of getting stuck in a loop where people want to be vulnerable with each other, but they can't because they don't want to be the first one. [laughs] So I'm really thinking a lot about what are ways to break out of that and I don't know, it might just involve finding ways that people can be vulnerable about maybe something a little bit lower stakes and see if you can iteratively build up on that. Yeah, I'm thinking a lot about that like, how do you evolve the culture to enable vulnerability a little bit more?

CASEY: I'm taking away some metaphors and I wish I wrote them all down, but I have to go through the episode again. I remember Andrew's river metaphor, that it's wide, or narrow and you might have to row, or not and Arty, your cardboard cutout that if someone's arguing with you, you can imagine the cardboard cutout of yourself that they're working with to separate it from you. That visual metaphor is so powerful, I can't wait to use that myself sometime.

Andrew, how about you?

ANDREW: For me, to add to your list of metaphors talking about psychological safety, building psychological safety, and building a culture of being able to share vulnerable things and be able to provide each other feedback. That really builds the strong foundation so that you can build the house—the house being the project that you're actually doing, the work that you're doing without that strong foundation. I think the house is shaky. Doesn't have that firm foundation.

On the subject of being vulnerable and how do you break into that vulnerability, I think it's important to acknowledge the leadership here. Being the first to be vulnerable and being the first to follow are both demonstrations of leadership. So if you're looking at who on your team you'd like to nominate, or select to be your next leader, to create that sense of that culture shift, the person who's vulnerable and the person who follows, I think are great people to look at.

CASEY: Like that TED Talk, the first follower.

ANDREW: Exactly.

CASEY: I think you showed me that years ago, Andrew.

ANDREW: [laughs] Yes. The TED Talk about dancing on a hillside.

Right at the end here, if you don't mind, I'd love to put in a little plug. 18F is a part of the federal government and that means that I'm a federal employee and a civil servant. My salary is paid by all the folks that are paying the taxes. I just want to put on a plug for civil service. Not necessarily for 18F; that's just the area where I've found my talents seem to be best used.

But maybe for you, dear listener, that is your local government, maybe that's your state government, or maybe that means running for office. The government that we have is not perfect. It is the best one we figured out how to create and if you want to be involved in changing what the best is, or demonstrating that what we have is not as good as what you want, one of the great ways to do that is to be involved in changing it.

So if you haven't considered looking for a position as a programmer, as a project manager, as a product person, designer, all across the board, the government both, federally and state, and locally needs people like that so, trying to find those and figure out how to support them.

ARTY: Well, thank you, Andrew, for joining us. This was a great conversation.

ANDREW: It was such a pleasure. It was an honor to be a guest and hope you all have a great day including those that are listening.

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