How to Trust Again – Justin Searls

Why has trust become so rare in the software industry? Developers don't trust their own ability to program, teammates don't trust each other to write quality code, and organizations don't trust that people are working hard enough to deliver on time.

This talk by Justin Searls is a reflection on the far-reaching consequences distrust can have for individuals, teams, and organizations and an exploration of what we stand to gain by adopting a more trustful orientation towards ourselves and each other.

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01:57 - Justin’s Superpower: Having Bad Luck and Exposing Software Problems

04:05 - Breaking Down Software & Teams

• Shared Values
• Picking Up on Smells to Ask Pointed Questions
• Beginner’s Mindset
• RailsBridge

12:49 - Trust Building

• Incremental Improvement
• What Got You Here Won't Get You There: How successful people become even more successful by Marshall Goldsmith
  • Credibility
  • Reliability
  • Intimacy
  • Selfless Motivation
• Authenticity
  • Detecting Authenticity
  • Laziness Does Not Exist

29:14 - Power Politics & Privilege

• Leadership Empathy
• Safety
• Exposure; “Don’t Cross The Net”
• Masking

42:06 - Personal Growth & “Bring Your Whole/True Self”

• RubyConf 2019 - Keynote: Lucky You by Sandi Metz

How to Trust Again – Justin Searls

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Transcript:

PRE-ROLL: Software is broken, but it can be fixed. Test Double’s superpower is improving how the world builds software by building both great software and great teams. And you can help! Test Double is hiring empathetic senior software engineers and DevOps engineers based in the United States and Canada. We work in Ruby, JavaScript, Elixir and a lot more. Test Double trusts developers with autonomy and flexibility at a remote, 100% employee-owned software consulting agency. Looking for more challenges? Enjoy lots of variety while working with the best teams in tech as a developer consultant at Test Double. Find out more and check out remote openings at link.testdouble.com/greater. That’s link.testdouble.com/greater.

JACOB: Hello and welcome to Episode 270 of the Greater Than Code podcast. My name is Jacob Stoebel and I'm joined with my co-panelist, Mae Beale.

MAE: And I'm joined with another panelist, Chelsea Troy.

CHELSEA: Hi, I'm Chelsea and I'm here with our guest, Justin Searls.

He's a co-founder and CTO at Test Double, a consulting agency on a mission to improve how the work writes software. His life's work is figuring out why so many apps are buggy and hard to use, why teams struggle to foster collaboration and trust, and why it's so hard for organizations to get traction building great software. The Test Double Agents work with clients to improve in all of these ways and more.

Hi, Justin! How are you today?

JUSTIN: Hello. I'm great. Thank you so much for having me.

CHELSEA: Of course.

So we like to kick off our sessions by asking you, what is your superpower and how did you acquire it?

JUSTIN: Well, one superpower might be that I like to give counterintuitive answers to questions and [laughs] my answer to this would be that I have really, really bad luck software and hardware. My entire life has just fallen over for me left and right. Bugs come and seek me out. In college, I was in the computer science program and so, I was around a lot of computers, like Linux data centers and stuff, and I think I went through either personally, or in the labs that I used 20 hard drive failure years in 4 years. People started joking that I had an EMP around me.

So I started to just decide to lean into that not so much as an identity necessarily, but as a specialty of root cause analysis of like, why do things fail? When I see a bug, what does that mean? And to dig in to how to improve quality in software and that then extended to later in my career, when I was working on delivery teams, like building software for companies and institutions. That meant identifying more root causes about what's leading to project failure, or for teams to break down.

Now I'm kind of moving, I guess, popping the stack another layer further. I'm starting to ask what are the second and third order consequences of software failing for people having for others? I see this in my family who are non-software industry family members, when they encounter a bug and I'm watching them encounter a bug, their reaction is usually to think that they're the ones who screwed up, that they're stupid, that they just can't figure it out. I'm literally watching software that somebody else wrote far away just fail and that's just no good, right?

So I think that the fact that I just so easily expose problems with software and sometimes the teams that make it almost effortlessly, it's really given me a passion and a purpose to improve and find opportunities to just make it a little bit better.

MAE: When you talk about software and/or teams breaking down and you're mentioning bugs. So I'm assuming that that's mostly what you mean by breaking down? I'm curious if you have kind of a mental model of software always breaks down these four ways. Teams always break down these three ways. I don't know if you have any reference texts, or things that you've come across as far as like a mental model for what is the world of breaking down? How do we characterize it?

JUSTIN: That's a great question and I feel like having been basically doing this for 15 years now, I should be prepared with a better answer.

I've always resisted building I guess, the communicative version of an abstraction, or a framework for categorizing, simplifying, and compartmentalizing the sort of stuff that I experience. In some ways, my approach [laughs] is the human version of machine learning where I have been so fortunate, because I've been a consultant my entire career, to be exposed to so many companies and so many teams that that has developed in me a pattern recognition system that even I don't necessarily understand—it's kind of a black box to me—where I will pick up on little smells and seemingly incidental cues and it'll prompt me to develop a concern, or ask a pointed question about something seemingly unrelated, but that I've come to see as being associated with that kind of failure.

I think your question's great. I should probably spend some time coming up with quadrants, or a system that distills down some of this. But really, when I talk about bugs, that is a lagging indicator of so many things upstream that are not necessarily code related. One of the reasons I want to be on the show here and talk to you all the day is because I've been thinking a lot about trust and interpersonal relationships starting with us as individuals and whether we trust the work that we're doing ourselves, or trust ourselves to really dive in and truly understand the stuff that we're building versus feel like we need to go and follow some other pattern, or instructions that are handed to us.

To kind of try to answer your question more directly, when I see teams fail, it usually comes down to a lack of authentic, empathetic, and logical targeted relationships where you have strong alignment about like, why are we in this room? Why are we working together? How do we best normalize on an approach so that when any person in any role is operating that is consistent with if somebody else on the team had been taking the same action that they would operate in the same way so that we're all marching in the same direction?

That requires shared values and that requires so many foundational things that are so often lacking in teams as software is developed today, where companies grow really fast. The pay right now is really, really high, which is great, but it results in, I think a little bit of a gold rush mentality to just always be shipping, always be hustling, always be pushing. As there's less time for the kind of slack that we need to think about—baking in quality, or coming back to something that we built a couple weeks ago and that maybe we've got second considerations about. Because there's that kind of time, there's even less time sometimes for the care and feeding that goes into just healthy relationships that build trust between people who are going to be spending a third of their life working together.

CHELSEA: You mentioned picking up on little smells that then lead you to ask pointed questions. I think that's really interesting because that kind of intuition, I've found is really essential to being a consultant and figuring out how to ask those questions as well. Can you provide some examples of situations like that?

JUSTIN: Yeah. I'll try to think of a few.

I had a client once that was undergoing—this is 10 years ago now—what we called at the time, an agile transformation. They were going from a Waterfall process of procuring 2 year, $2 million contracts and teams to build big design upfront systems that are just thrown over a fence, then a team would go and work on it, and then it would go through a proper user acceptance testing onto something more agile, I guess. Adopting Scrum and extreme programming, interpersonal process, and engineering practices. That was just meant to be more, I guess, iterative of course, innovative, collaborative, more dynamic, and able to let the team drive its own destiny.

All that sounds great and you walk into the team room and they just invested millions of dollars into this beautiful newly restored historic building. I sit down with everyone and I look at them and they've got the cool desks at the time and cool open office because those were still considered cool. I sat down and I couldn't help, but—[chuckles] this is real silly. I couldn't help but notice that there was a pretty strong smell, [laughs] body odor throughout the whole room and it wasn't one person. I'm not picking on somebody here.

It was that the interpersonal relationships were so afraid, the fear of failure was so strong, and the deadline pressure that had been exerted from on high was so overwhelming that there was no safety in the room. People were just scared at their job all day long and it was having a material impact that only an outsider who's walking in at 2:00 PM on a Friday detect because everyone else had acclimated.

So I walked in and I was like, “Well, what do I –?” [laughs] Obviously, I'm not going to be like, “Hey, it stinks in here.” I’ve got to figure out a way to understand why do people feel unsafe and maybe I didn't have that sentence go through the voice in my head, but it definitely put me on a path towards to maybe the less privileged people in the room, the people who are not the managers to understand what's really going on, what pressures are they under?

MAE: I love that the example includes legit real smell. So many times, especially in our industry and part of what this podcast is counteracting, is getting in touch with the fact that we are people and humans. Anyway, I love that you brought [chuckles] that home that way.

Also, I wanted to say from earlier, I wasn't trying to corner you into expecting to have a philosophy. I thought you might and it was worth asking. But I recently got asked a similar question about my management philosophy and which authors do I appreciate most, or something. I've been a manager for 25 years and I'm like, “Uh. I don't know. I figure out what is needed and then I deal with that.” I don't understand how to answer. So I just want to give some – pay you back and apologize. I didn't mean to get you – [overtalk]

JUSTIN: Not at all and it becomes one of those you know it when you see it.

I struggle with this a lot because somebody introduced the concept years ago of beginner's mindset to me where sometimes if I'm a beginner at something, the best person to help me is not the expert—the person who's been doing it for 20 years. It’s somebody who's just a few hours, or a few days, or a year, or two ahead of me because they can still remember what it felt like to be where I am right now.

Because I talk a lot, because I tweet a lot, because I show up in a lot of places, and I have an outward facing sales role to potential clients and candidates, I meet a lot of people who come to me and they're like, “How do I learn how to code?” And I'm like, “I can tell you the 15-year version of this story, but it's probably going to be really depressing.” I've taken as a responsibility to like try to—and I need to do a much better job of this—be armed with either resources, or people that I trust, that I can refer folks to so that I'm not totally leaving them hanging.

MAE: I love that and yes. Speaking of teaching people how to code and what you said, there's a name for it that I'm forgetting about being a teacher. If you are closer to the student, you actually are a more effective teacher.

So there's just two comments.

The first one is I'm a part of RailsBridge I helped found the Southeast regional chapter. So if anybody, any listeners out there still want to learn how to code, or are having that same, I don't know how to tell you about my [chuckles] zigzag story and ideally, they wouldn't all be depressing, [laughs] but I'm sure they all include some real low moments. But RailsBridge, which is bridgetroll.org, has recurring events where people can go all over the country and obviously, in pandemic times it's not as much in person, but yeah.

And on the comment about teaching and when you mention talking to the people with the least privilege in the room, I'm just really sensitive and appreciative of your sensitivity to power politics and how much they impact so much of what is happening and trust. So for anybody out there who's being asked to help new people and you feel like you're still the new person, you're probably in a better position to help. So just want to offer some encouragement there. I have personally found a lot more confidence in helping people who are just behind me and that anytime you're teaching, you're learning. So just want to put those in.

I love that actually your answer, instead of a quadrant, is really just the one word of trust and I appreciated the ways in which you were mentioning trust can be different things. Trust in what you're building. Trust in who's asking you to do it.

Chelsea asked for a couple examples and I interrupted. So I apologize, but what are some trust building exercises that you have encouraged, or examples? Maybe even continuing that same story. Six months later, was it a fresher air in there and what are some things they did to make that happen?

JUSTIN: Yeah, that story, like so many teams and companies in our industry, didn't undertake the redemption arc that I wish I could convey. I think in fact, to see a big picture problem and the desire to connect that with a big picture tidy solution, a future state where it's all rainbows and unicorns and everyone really getting along well.

Sometimes that sets, for me personally and when I see consultants who are less experienced, who can see that end state in mind and they know maybe the top three hit list of stuff that needs to happen to help that organization get to where they need to be. We can sometimes set the bar so high for ourselves in terms of expectations of like, what does it mean to help them become better, that we can't help, but lose sight of the value of just incremental improvement.

If I can just help restore relationship between two people on a team. I had one client years and years ago, [laughs] they were also undergoing a pretty big transition and they brought me in a – I think that what they thought they were hiring me for was to be a test-driven development coach to teach them that particular practice of TDD.

They got, instead on day one, there was a room of 30 interdisciplinary cross-functional teams—some developers, some non-developers, and stuff—and I could just tell that they were like, it was a big epic rewrite from a Perl codebase that, I think they were moving to no JS and Angular as well as a chewing of cloud infrastructure at the same time, as well as Agile software practices at the same time.

They were overwhelmed, they've seen this fail before, they felt a ton of pressure from the business, and they didn't even really understand, I don't think, the future business model. Even if they were successful, it wasn't clear this was going to solve systemic problems for the company. And I'm like, “Well, I can teach you all TDD. [laughs] But instead what my commitment to you all will be is that six months from now, you'll either have been successful and learned all of these things and built the thing as the business has asked you to do and then the business takes off, or I will have helped equip you with skills and ways of thinking about this industry and our work that will set you up to get much better jobs next time.”

Again, the company didn't totally come together. It didn't take off like a rocket ship. The team was successful in the rewrite, which doesn't happen very often. But then you saw almost a diaspora of dozens of highly skilled people—and this was in Central Ohio—who then went to venture backed startups, some went to big, established enterprise-y kind of companies, some left the region and went elsewhere.

That turned into, if I had to count, probably eight, nine additional Test Double clients [laughs] down the road where they came in and they could spot in a minute, this is a way that an outside perspective, who is here to help us at a moment of tremendous need, can move the needle just a little bit. By setting expectations realistically, being humane about it, and focused on what's best for the people involved because at the end of the day, all companies are is collections of humans. That was, I guess, more my orientation.

CHELSEA: So Justin, I'm interested in your thoughts on this. I appreciate what you just shared.

I worked at Pivotal Labs for a while—original labs when it was sort of a generalist’s enablement.

JUSTIN: Sure.

CHELSEA: Very heavy on that kind of thing.

One of the things that we ran into relatively frequently was similar to what you've just described wherein one of two things would happen. Either the clients were successful and there was a vastly improved, I guess, software delivery culture among the people that we were working with, or if that didn't work out, then there were individuals who took to it very well and had gained variety of skills that allowed them to go elsewhere.

It happened enough times that then we would have to establish trust with potential new clients around this whole additional access, which was effectively, is this going to cause a diaspora of all of these engineers, designers, and PMs that I've managed to scrape together for this project?

Do you find Test Double ever facing that, or how do you address either beforehand if product owners are aware of it, or after it happens, how do you address that with clients?

JUSTIN: That's a fantastic question. Pivotal Labs was one of the companies that we looked at.

We started Test Double 10 years ago. I was at the time, just starting to speak at user groups and conferences and I spent a lot of time with the people at the Boulder office at Pivotal Labs. Great people. I really appreciated the focus and the rigor and in fact, made to answer a question earlier about process, or abstraction about like, “Hey, boil it down for me.”

Pivotal Labs sold a very branded, very discreet process for like, this is the way to build software and, in a sense, some of the decisions that we made when we started Test Double were a response against that. Just to say we trust the people closest to the work to make the right decisions based on tremendous experience and skills. Frankly, as we get bigger and more successful, having some somebody like me at the top of an organization who only talks at the beginning of a client relationship, which is the moment that we know the least and I've got the least amount of context, for me to go and say, “Well, this is the way that we got a test,” or whatever it is would just be ineffective and inappropriate.

So to answer your question, Chelsea. Fortunately, our brand power, isn't nearly as strong as Pivotal Labs so no client has ever come to us in advance with that as a question to say, “Hey, I'm worried that you're going to train our people in this particular methodology and then they're going to leave for higher paying jobs,” or something. That's never come up in advance.

In fact, one of the things that we talk a lot about is that because our consultants join client engineering teams to work with them inside of their own process, using their own tools, and their own system is we just try to be model citizens of somebody on that team. We trust our clients like, “Whatever your process is, it's apparently working for you. So let's just try it and if we have ideas for how to make that better, we will listen, we'll write them down.” But then only once we've built trust and rapport with the people on that team, will we start to share, “Hey, I've got a rainy-day list of a few things that you might want to try.”

What that's actually done is has a detoxifying effect where from a context of high trust, the incongruity, the distrust, the kind of backchannel frustrations that our people pick up on because we're kind of “in the trenches” with our client folks, we're able to have multiple pathways into that client organization to help make it a better place to work.

We got one of the best poll quotes that I've ever seen on our website recently. One of our clients is Betterment. They're a great financial management firm in New York where it's kind of an autopilot savings vehicle. The director of engineering, Katelyn, there said that she saw on the teams where testable people were deployed, attrition actually went down and I think it's because we help those teams to perform better.

An old friend of mine named Leon Gersing, he used to have a thing he’d say. He'd said, “You can either change where you work, or you can change where you work.” Meaning you can either make the place that you're at better, or you can go find gainful employment elsewhere and we're in the make the place where people work better business, wherever possible as a first avenue.

MAE: You're reminding me of a book that I'm reading right now called What Got You Here Isn't Going to Get You There. Are you all familiar with it?

JUSTIN: I was so proud of my wife, because she asked for that on Audible earlier this week because I'm the person with the Audible credit and I'm like, “Oh, this is quoted in business leadership contexts left and right and all over the place. So it'll give us a touchstone to talk about.”

MAE: Yeah. Well, the TLDR is so much of especially management focused and leadership focused thought is about things that you should do and this book is probably along your lines, Justin of giving the counterintuitive answer. This is here's 20 things that you might want to consider not doing and then replace it with the good behavior because that is such a stretch in real life to actually do that. It's how about you just pick a couple of these that you're a repeat offender and just stop. Just try to not do it. That's the main first thing and I've found that, a refreshing take on how to think about how to guide in ways that are building more trust and offering more safety. So definitely recommend that book.

I don't know that it came out of this book, but the person who recommended it to me, my VP Scott Turnquist, who is amazing, shared that there are really four categories of things that can help build trust and it's definitely all done incrementally. So picking up on that word you said earlier, Justin, too. But the four kind of axes are credibility, reliability, intimacy, and selfless motivation. If you can demonstrate those recurringly, that is how to establish and/or course correct into a state of increased trust.

So anyway, that was partly why my original statement was like, do you have this down? Because I've heard some things lately that I've been thinking about.

JUSTIN: I really appreciate your perspective there and it makes me feel better because one of my commitments in life is to never write a book. But if I were to write a book, I'd probably have to come up with a tidy quadrant, a Harvard Business Review two by two, or something like that to I guess, support the good work at the people at CliffsNotes and Blinkist to boil down years’ worth of work into a 13-minute podcast.

I think that the advice as you expressed, it is completely valid and there's one thing that I think is a core ingredient to trust. Trust of ourselves, trust of people that we work with directly, and then trust of leadership and the people who run the organizations that we're a part of.

The hardest, in my opinion, is authenticity. If you're not, I think you said credible. If you combine credible, intimacy, vulnerability, those are really useful words to prompt what I mean when I say authenticity. If I'm talking to somebody and I can lock eyes with them and I believe that what they're saying is what they actually feel and it's their true self and they believe it, then all sorts of other background processes in my head of trying to read the tea leaves of what's going on here, all the passive analysis I might do to try to understand what's the subtext that this person's operating from. That's just the form of kind of armor, or a guard that it depletes my cognitive ability to talk to the person.

Authenticity is a signal that we pick up on as humans and this is why it's a miracle that we have video chat in this era and it's why I really relish one-on-one in-person interactions when I can have them. Authenticity is a signal that I can drop that guard a little bit. It's that I can really look and really listen to what the person's saying and take it at face value. The problem with just saying, “Oh, okay, well just be authentic. Just be your true self,” is that that is useless advice and way more likely to trigger somebody's defenses, or their self-doubt.

When I think about authenticity in the context of a team, or an organization is that the people who are maybe not in a position of power, people who report up the chain, if they don't come across as authentic to their leaders, the leaders should not look at that as a failing of the person, but as a failure of their ability to figure out how to promote and draw out authenticity from the people who report to them. Maybe they don't have safety in the room to speak their true mind. Maybe they feel like the things that make them different from the other people that they work with are a liability, or a risk and so, they can't really bring their true self to work.

It's the leader's job, when they spot inauthenticity, rather than go on a hunt like a political backchannels to try to figure out why is this person lying. What's under here? Figuring out what is it about the person's context, the environment, kind of the system that they are operating in. What could possibly be an explanation for why I can't develop an authentic connection with this person? And until you run out of every single possible explanation in that investigation, including self-reflection of what is it that I'm individually doing and how I communicate to this person that's getting in the way. Only then is it really useful to start thinking about maybe this person's not a good actor, maybe they're being duplicitous, or something. Because once you've hit that button, it is really hard to go back.

So when we talk about authenticity, we often talk about the individual's responsibility to present it, to be it. If you can fake authenticity, then you can do anything, right? That is advice. It's fine. I hope that everyone feels the safety. Like I'm a cishet white dude who's pretty powerful in my little corner of the small pond. I have no problem just spouting off and being my true self and so, I should just tell other people to do that too. That's not fair.

I think that what is better advice for people who are maybe not in positions of power is to be really good at detecting authenticity. When you detect authenticity and people are making their true selves known to you and you're feeling a connection with them, whether they're peers, or managers, spend more time with them, invest into those relationships, and use those people as anchors of trust. So that when you're failing to make that connection elsewhere, when you have doubts about others in the organization, you can have more points of perspective on how to best address it.

MAE: I read an article yesterday that says, “Laziness Doesn't Exist.” That's the title of it and it essentially says that that same thing of what's the context in which this is happening. People don't procrastinate for fun. In fact, it usually takes more work and starting from a place of what shoes are you in, but I especially love the in what way am I impacting that person's ability to be themselves?

Also, I must have said the word authenticity, because this list is credibility, reliability, intimacy, selfless motivation, but authenticity and credibility in all of these things do also have to do with the thing that I loved you bringing up about identity, power politics, and what happens and your environment is not allowing you to be credible. So another way in which people can as good peers, mentors, managers, and above can do is in what way am I bolstering these people's credibility?

So always flipping it back to how are we the perp [laughs] and that's very similar to social justice, racial justice. The more we see how we are perpetuating and disenfranchising, regardless of our identity, that's where there's some hope for the humans in my mind.

CHELSEA: Yeah. One of the things that I appreciate that you've both brought up, Justin and Mae, is the degree to which power gradients play a role in the way that we deal with these things. There are demographic power gradients with regard to race, with regard to gender. There are also power gradients with regards to our position in the company, with regard to technical privilege, with regard to our level of skill, with regard to the size of our network.

We also, I think live in this individualist culture that has a tendency to place the responsibility on individuals to do what they can to resolve. For example, what you were saying, Justin, about how we effectively coach people to just be authentic. Maybe that coaching works fine in some context, but that's a subset of the context in which we're asking people to apply it and asking individuals to resolve this from the bottom up sometimes as opposed to looking for the systemic reasons why this is a thing that has to be solved in the first place.

I'm curious as to whether you have thoughts on what a person can do, who finds themselves in a position of power, in a position of leadership in a company, for example, to address those sorts of questions with other folks who are working there.

JUSTIN: I think one thing that can be helpful – and I realize your question is about what can a leader do. One thing that can be helpful is for those leaders to empathize and put themselves in the shoes of people who might not have the same privileges as you described and what would it take to—I'm waiting outside my area of expertise here—would be to think about what are the things that are in a given person's sphere of direct control, what isn't, what am I setting up, and what am I communicating in terms of expectations that I have of them?

An example that came up a lot in our industry was the number of drink up events in tech in the early 2010s where there was sort of an assumption that everyone likes alcohol and when people in public drink alcohol, good things happen, which turns out isn't true, but it can also be the case.

There are invisible expectations that we communicate because I'm a big fan of granting people autonomy to solve problems in their own way, to approach work the way that they feel is best. Our company has been remote from day one and a big part of that was we want people in control of everything from where they work to their home network, to the computers that they use. Because when I had that control pulled away from me in the role as developer, it just sapped my motivation, my drive, my engagement, my sense of control over the stuff that's right in front of me.

When I now in a role of influence over other people, whenever I speak, I have to think about the negative space of what are the expectations that I might be conveying that are not explicit. I need to be careful of even expressing something like hobbies, or shows that I like, or stuff – especially in this remote world, we want to develop connectedness.

But a challenge that I keep running into is that our ability to find mutual connection with people about stuff other than work, it rides the line really closely of communicating some other allegiance, or affiliation whether that's we talk about sports a lot because that's an obvious one, but even just interest in hobbies.

So I find myself – and I realize Chelsea, I'm doing a really poor job, I think of answering the question as you asked it. I find myself only really able to even grapple with like what can leaders do to set the tone for the kind of environment that's going to be inclusive and safe for other people by really digging in, empathizing with, calling up, and dredging up what their own experience was when they were not in a position of power.

If I have a secondary superpower, is I had a real rough start to my career. I was in really, really, really rough client environments that were super hostile. I had a C-level executive at a Fortune 500 company scream at me until his face was red in a room one-on-one with a closed door on a regular basis. The sorts of stuff that developed callus on me, that I look back at a lot of those experiences and I'm like, “I learned a bunch.” It's supercharged my career as an individual because it strengthened me.

So the challenge that I have is what can I take from those really, really harsh experiences and translate them for people who are coming up in a way that they don't have to go through the same trials and tribulations, but that they can take away from it the lessons that I learned. And for me, it's all about not just safety for the sake of safety, but safety by which myself and others can convey the useful growth that people want to see in themselves, their skills, and their abilities that isn't diluted. That can convey the truth, the difficulty, and the challenge and how hard –

Programming is really, really hard for me and I've been doing it for a long time. A lot of stuff about this is just not easy. The relationships are not easy. Like you're going to run into situations where there's massive differences between where people stand on stuff and what those perspectives look like. Navigating that is hard enough without adding a whole layer of toxicity and hostile work environment.

So what's a way to promote that learning environment without just totally insulating somebody from reality. That's been, I think a challenge and attention that I see a lot of other like-minded leaders in tech trying to figure out how to create.

MAE: You reminded me of a meme that someone shared with me that says, “What doesn't kill you can just regulate your nervous system, trap itself in your body, steal your sense of self, make you wish it did.” I don't know what makes you stronger means, but let's stop glorifying trauma as a life lesson we've been blessed with. [chuckles] Definitely along the same lines.

JUSTIN: Yeah. Relatable.

MAE: There's a thing, too about putting oneself in another's shoes and this is a place where I'm someone that can read people really well, but that makes that tricky. Because I start to trust my sense of it and I have a similar architecture going if I don't feel like I'm getting the whole story. So what's the read between the lines thing.

But without a lot of exposure to a lot of very different people, and most people have not had a lot of exposure to a lot of different people, when they put themselves in the other person's shoes, they come up with a different conclusion. So I will feel hurt by people who do things that were I to put myself in their shoes would not have done that to me, or if they did, it's because of X, Y, Z about who they are, or what they think, or what is their whole context and environment.

All of that is there's a tactic that we use at True Link Financial called “don't cross the net.” So you say and claim the story I tell myself about that is dot, dot. When leaders, who haven't had a lot of exposure to a lot of different people and a lot of different ideas, try to empathize and find themselves limited in that, there are other options which include one of the things you said earlier. Making it so that people can say the things on their mind so whether, or not that's persons being their authentic self this is a whole another level, but creating a place where we expect that we're all messing up and that it's okay to talk about uncomfortable things is one of my real soapboxes.

It's totally okay. Yes, we are all racist. We are all sexist. We are all homophobic. There is no way to not be as a result of being in the culture we're in. We could do things to mitigate it. We can do things to name it. But if we just start from yes, we're all failing. This for me, it lowers the stakes because so many people feel that if someone brings up, “Hey, that's kind of sexist,” or “This is not supporting me in this way,” or “My credibility is not being seen because of this.” In the absence of already, yo, we're going to talk about some negative stuff sometimes, that's an introduction of negativity to the “positive, happy rainbow unicorn workplace” that you were talking about before.

So one of my hopes and dreams is that we get some clouds to rain on the land to allow things to actually grow [chuckles] and this includes, yo, we are not perfect. And we are definitely doing things we don't intend all the time.

JACOB: That made me think about authenticity again, because sopen about imperfection. I'm a neurodiverse person so I probably am autistic. If someone were to say to me at work, “We really want you to bring your authentic self,” probably the thing I would think is you don't want that person, [laughs] or at least without getting to know me a lot better.

There's a concept called masking where it's basically, there are behaviors and traits that are exhibited by neurotypical people that just come naturally to them. By learning the hard way, I've sort of learned to do them, even if they don't feel natural at all like making eye contact, smiling at people when talking, things like that. So I think that complicates authenticity for me, which is that I'm intentionally not hiding, but choosing what parts of myself to show and what parts I just don't want to bring to work. [laughs] I don't have a clean answer for that, or a solution to that, but I think that just complicates things for me.

JUSTIN: I thank you so much for sharing that and I think it's a really important perspective to bring, which is I talked earlier about sure, plenty of people's true, authentic selves, even if they were to bring them, they might be in a job, or in a space, or in a team where that wouldn't be understood as such, or appreciated, or literally safe. It's hard to tell people, “Hey, you should feel safe” when the truth when spoken would be an unsafe thing. That would be setting people up for risk, for danger, and it would be a seed of distrust, which is what we're all here to talk about avoiding. So I really appreciate you sharing that.

When I talked about empathy earlier, Mae, in my brain, all that really comes through it is the E-M part of that word, like the root for emotion. I never really have been able to assume that I can get somebody's context, their perspective, and the moment that they're in into my brain well enough to role play and do a re-dramatization in black and white, sepia tones and slow motion, like this is what Justin would do if he was here.

That's one reason why we trust people at our company to just do the work, because we know that they're going to have such a richer amount of data and context than we'll ever have. But one thing that I'm grateful for is that I've been able to experience what I feel like is a pretty broad range of emotion. [laughs] I'm a real emotionally volatile person. I go super high highs, super low lows and I'm just like, it's how I've been. I can't help it. So when I'm empathizing with people, I'm just trying to get in the mindset of how do they likely feel right now so that I can understand and try to do a better job, meeting them where they are.

A big part of that is learning there are differences and so Jacob, of course, it’s like if I worked with you, I understand that it might not be productive to bring all of yourself to work all the time. But I would hope to develop a trusting relationship with you where you can share enough so that I can know what are the boundaries that are going to be productive for you, productive for me so that we can make a connection and it's something –

To make this a little bit more personal. I don't know where my career is going to go next. I founded Test Double with my partner, Todd. I was only 26 years old and we've been doing this for 10 years now. 2 years ago, we embarked on a journey of transferring a 100% of the equity of the company to our employees. So we're on an employee stock ownership plan now, it's ESOP, or any of the stuff, it is complicated because it's well regulated. We have to have outside auditors, a valuation firm, we have a third-party trustee to make sure that our people and the value of the company is transferred appropriately, treated right, and managed well.

So it's naturally raised, especially in my circle of friends and family who realize that, this means that there's not an end date, but there's a moment at which I can start thinking about what my life is going to be next. The people who knew me when I was 25, 26, who look at me now, it's not that I've changed radically, or my identities are radically different, or anything. It's like, I am a very different kind of person than I was at 26, than I was at 20 before I got into this industry.

I have changed in healthy ways and in maladaptive ones and in response to maybe drama and stress such that the ideal retirement that I would've imagined earlier in my life looks a lot different now where I've just kind of become habituated. I'm a really, really different person than I used to be and I'm grateful for that in almost every way. I feel like I've grown a lot as a person, but the thing about me that I really look at as an area of change is that I just work too much. [chuckles] I'm online all the time. I'm very focused on – I've optimized productivity so much that it's become ingrained in me.

I understand that whatever I do next, or even if it's just changing my role inside my company, I need to find a way to create more space for slower paced asynchronous thought and learning how to, in the context of a career, not just bring your true self – I'm kind of curious Chelsea, Mae, and Jacob's perspectives. That true self might be changing [laughs] intentionally. There's a directionality and the growth isn't just learning new skills necessarily, but it might be changing core things about ourselves that will alter the dynamic of the relationships that we bring to work.

CHELSEA: Yeah. I have two thoughts on that, that I can share.

The first is the extent to which bringing my true self is a productive thing to do at work. So for example, my career prior to tech, I did a variety of different things to make ends meet, really a wide variety of things. I graduated directly into one of the bigger recessions. I won't tell you the exact one, because I don't feel like being aged right now, but [chuckles] it wouldn't take too much research to figure it out. I was trained to do a government job that was not hiring for the next 18 months at a minimum. I needed to figure out what to do and was trying to make ends meet.

In my first year of employment, I got laid off/my job ended/something like that on four separate occasions in my first year of work and that resulted in, I do not trust when managers tell me that everything is fine. I have not ever effectively and that is something that I don't foreground that in work discussions for a variety of reasons. I don't want to scare other people. I don't want them to think I know something that they don't know about what's going to happen because I don't usually.

When managers tell me, “Oh, everything's great, we're doing great,” all that kind of stuff, I just don't listen. I don't. My decisions do not take that's statement into account and I find that that's the kind of thing that I think about when I'm asked to bring my whole self, my authentic self to a place is that there are things that just sort of similar to what Jacob is saying. I'm like, “Trust me, trust me on this you don't want that.” So that's kind of the first thought in that realm.

The second thought that I have around this is the degree to which work should really encompass enough of our lives to require, or demand our authenticity. So I had a variety of full-time jobs in tech and then I quit one of those full-time jobs and I was an independent consultant for a while bolstered chiefly, and I was lucky for this, by folks who had read my blog and then folks who had worked with me when I was at Pivotal. So the consulting effect of people knowing what it's like to work with you is real.

That experience felt very different from a full-time position insofar as at the external validation of my work was naturally distributed in a way that it's not in a full-time position and I found that distribution is extremely comforting. Such that even though I now have a full-time job, I also continue client work, I continue teaching, and I continue writing and doing workshops and those kinds of things.

This is not the chief reason that I do that, but one of the nice things about it is the diversification of investment in the feedback that I'm receiving and validation that I'm receiving. In order to do that, I have an amount of energy that I put to each of the things in my life and part of it is work, of course. But another reason that I think it works for me is that I no longer have to expect all of my career fulfillment from any one position, from any one employer, from any one place, which has worked out very well because I think that we pedal this notion implicitly that you bring your whole self to work and in return, work provides for your whole career fulfillment.

But most places really kind of can't and it's not because they're terrible places to work. It's just because the goals of a company are not actually to fulfill the employees, they’re just not. That's not the way that that works. So it has allowed me and I think would allow others to approach the role that a given employment situation plays in their life, from what I think is a more realistic perspective that ends up helping keep me more satisfied in any given work relationship. But it doesn't necessitate that I – I guess, for lack of a better term, it limits the degree of emotional investment that I have in any one thing, because I'm not expecting all of my fulfillment out of any one thing.

But I think that to say that explicitly sometimes runs at best, orthogonal and at worst, maybe contraindicates a lot of what we talk about when we talk about bringing our whole selves to work and looking for those personal connections at work. I think there is pragmatic limit past which we maybe impose more guilt than we need to on ourselves for not doing that.

JUSTIN: Yeah. Thank you so much for sharing that.

I think Mae used the phrase “lower the stakes” earlier and I think that one of the problems with authenticity, the phrase “bring your whole self-trust” is that the stakes are super high because it seems like these are bullion contracts between parties. For example, you said that you don't trust managers. If I was filling out a form, like a personality inventory, or something, it's like, “Do you trust managers?” I'd say no and I think 90% of people would say no.

It’s sort of the economy right now. I think the economy approval rating of is the economy good, or bad is at 23%. But individuals are saying at roughly 60% levels, that they are individually doing okay in this economy. I would say the same. Like, do I trust my manager? Oh, hell yeah. I completely trust my manager right now.

And to lower the stakes even further, when I've been talking about trust, it's not so much about where do I find fulfillment, or who what's my identity, or who am I being, it's about a snap orientation. It's the most immediate sphere. “Oh man, this PostgreSQL query is really slow and I can't figure it out.” Is my snap reaction, or my orientation to think, “I believe in myself enough to dig into this to figure it out”, or is it doubt myself and just kind of get lost in a sea of a thousand Stack Overflow tabs and just slowly lose my whole evening?

When in a team, maybe working with them and we were in planning, or something, or maybe we're in a higher stake, let's say, a code review session and somebody makes a comment about something that I did. Is my snap reaction to doubt their motivations and think “Ah, they're just trying to passive aggressively shoehorn in their favorite architecture here,” or this is politics and gamesmanship, or is my snap reaction is to be like, “Nope, let's try to interpret the words that they're saying as literal words and take it on its face”?

Like I said, I'm a highly emotionally volatile person, the weather vane shifts with me all the time and sometimes I can control it and sometimes I can just merely observe it. But the awareness of the out has been really helpful to understand [chuckles] when I hear a leader say something about the company, my reaction is I think that they've got ulterior motives and that they are probably not speaking in literal truth.

If that's my snap reaction, I'm just trying to communicate that as that's a potential blind spot. Because I have a long rut of past companies that I worked for that had mission statements and vision statements that were kind of bullshit and that no one really believed in, that were just in a bronze plaque on a wall, or whatever. That's baggage that I carry. I just have to acknowledge that baggage and try to move forward. The best I can do is just be present in every moment that I'm in and to understand when I have a snap reaction, am I oriented towards what might lead me to a good outcome, or a bad one?

MAE: Holy moly, so many amazing things have been shared today and Jacob, especially kudos to you for walking us into a deeper level of authenticity. Love it. Thank you.

I'm, to answer some of your questions, Justin very similar to Chelsea in that tech was not my first rodeo. I didn't become a programmer until I was 37 years old and I am now 45. I'm totally fine with aging myself. Prior to tech, I did put a lot more of my identity in my job and I would usually do that job pretty much all of the hours possible and I've always worked for mission driven organizations.

A lot of the things that we're talking about as far as job fulfillment and whether, or not it's a good environment, or if it's a toxic environment, there's a lot of privilege in what we're talking. My parents were paper mill workers and it was not pretty. They had me when they were 19, so they didn't have another option. That was the highest paying gig in our region and they had no education. So it was never an option to even change that.

So I am someone who wants to put my whole self into what I do. It's a very working-class mode and gaining identity through what it is I'm able to do. It's also a pretty capitalist [laughs] mentality that I work to move around. But as a manager, when I am a manager, or in management, or managing managers, I'm never encouraging this everybody needs to bring their whole self to work.

Although, I had this really instructive experience where one person truly did not want to have any of their self at work, that they truly only wanted to talk about work at work. We're not a family, nicely nice. I don't want to crochet together, or whatever. That is the most challenged I've ever been as a manager because my natural things are always to figure out what people need and want, and then amalgamate that across the group and see how we can do some utilitarian math and get it so that people are being encouraged in ways they would like, they are not being disadvantaged, and they have space to say when that's happening.

But even still, I'm always going with the let's be buddies plan and it's not for everyone. So figuring out how to not have all of your eggs in any basket, no matter how many hours the job is, is definitely a tactic that has been successful for me. But what happens is I then am involved in so many things [chuckles] in all of the moments of life. So I still do that, but I do it by working more, which isn't necessarily the best option.

The thing about the mission that I just wanted to pivot for a second and say is, we are no longer in a world where we allow failure. This is a little bit back to my earlier soapbox. The energetic reality is whatever anybody's mission statement is, that is the thing they are going to fail at, like the seamstress never has the best hemmed clothes. So when we write off anyone, or any company based their flawed attempt at the mission, we're discounting that flaws exist, [chuckles] contradictions exist. It's about where are we orienting and are we incrementally moving toward that, or away from it and not in this moment, are we this thing that we have declared because it's more of a path is how I see it than the declaration of success.

JUSTIN: Yeah. Thank you so much for that, too. Because I think that one thing we didn't touch on is the universe – and we're talking a Greater Than Code podcast so it's software industry adjacent at least. The universe of people who got to stay home during this whole pandemic. The universe of people who are “knowledge workers”, or “white collar”, especially if you look at the population of the world, is vanishingly small.

There was a season in my life where I was the person that you just described managing, where I just viewed myself as I was burnt out. I always wanted to be a mercenary. I had this mindset of I show up at work. “You want some great code? I'll sling you some great code.” Like I was a short-order cook for story points and feature development and that was the terms, right?

I didn't want to bring my feelings to work. I didn't want to make friends with people because then God forbid, it would be harder to leave. I didn't have that available to me as a capacity at that time, but I went long enough and I realized it's not that I was missing something, or not being fed in some way by not having this emotional need filled at work. It was that I was failing to acknowledge when you say privilege, the literal privilege, that I get to wake up in the morning and think for a job [laughs] and the impact that I can have when I apply all of the skills, capabilities, and background asynchronous thoughts that are not literally in my job description.

When I can bring those things to bear, I'm going to have a much, much bigger impact because what am I except for one person thinking and staring at a matted piece of glass all day, but somebody who is in a small community, or a group of a bunch of people who are in the same mode.

So when I'm in a meeting, I can just be the mercenary jerk who's just like, “Hey, I'm just doing this,” and feeling like that's an emotionally neutral thing. When in fact, that negativity can be in an emotional contagion that could affect other work negatively, or and I'm not exactly –

My friends who know me, I'm a stick in a mud, I'm a curmudgeon, I'm super negative. I complain constantly and I have taken it upon myself to strive to be a net increase in joy in the people that I talk to and that I interact with at work. Because it is a resource that is draining all of us all day long on its own and it needs to be filled up somehow. I have the capacity right now to take it upon myself to try to fill that tank up for the people that I interact with.

So I want to touch on that because I just think it's super lucky that I get to work on a computer and talk out of a screen all day long. If I didn't have that, we wouldn't be having this conversation, I suppose, but I'm just here to make the most of it, I guess.

MAE: I love that. And you reminded me of Sandi Metz’s closer, Lucky You.

JACOB: Tell us about it.

MAE: She gave the closing talk a couple years ago and it's called Lucky You and it goes through how did we all come to be sitting in this room right now and what about redlining? What about the districting? What about all of these things that led to us to experience being here as lucky? I know you weren't saying it in that way, Justin, but it reminded me of that piece, too, which is relevant, but the talk is completely amazing and I definitely recommend it.

JUSTIN: I think I mentioned it once before. The thing that brought me and our marketing director, Cathy, to think that this would be a great forum to talk a little bit about trust at work is that we're about out to – and I think that actually the day that this podcast publishes is the day that we're going to publish a new conference talk that I've prepared called How to Trust Again and we're going to post it to Test Double’s YouTube channel. So we might not have a direct link for the show notes necessarily, but it'll probably be at the top of that as well as the top of our blog when the show goes live.

I hope that anyone [laughs] who enjoyed this conversation will also enjoy the kind of high paced, frenetic, lots of keynote slide style that I bring to communicating about a lot of these topics while still understanding that it's just like n equals one. I'm sharing my experience and hopefully, as food for thought to maybe help you look back at your own experience and understand what connects from my experiences, my perspectives, and my context that might be useful and I hope that you'll find something.

Special Guest: Justin Searls.

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