Managing to Balance the Unicycle with Amy Chantasirivisal

Amy (she/her) has spent the better part of the last 15 years in the tech start-up world, starting off as a front-end software engineer before transitioning into leadership. She has built and led teams across the software and product development spectrum, including web and mobile development, QA, operations and infrastructure, customer support, and IT.

These days, Amy is building the software engineering team at EdTech startup, Unicycle, and challenging the archetype of what a tech leader should be. She strives to be a real-life success story for other leaders who believe that safe, welcoming, and equitable environments can exist in tech. 

Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

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Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn. A famous quote was once uttered by Irena Dunn who said, “A woman without a man is like a fish without a bicycle.” Now, apparently at some point, people just, you know, looked at the fish without a bicycle thing, thought, “That was overwrought. We can do a startup and MVP it. Why do two wheels? We’re going to go with one.”

And I assume that’s the origin story of Unicycle. My guest today is Amy Chantasirivisal who is the Director of Engineering at Unicycle. Amy, thank you for putting up with that incredibly tortured opening. But that’s okay; we torture metaphors to death here.

Amy: [laugh]. Thank you for having me. That was a great intro.

Corey: So, you are, at the time of this recording at least, a relatively new hire to Unicycle, which to my understanding is a relatively new company. What do you folks do over there?

Amy: Yes, so Unicycle is not even a year old, so a company born out of the pandemic. But we are building a product to reimagine what the digital classroom looks like. The product itself was thought up right during a time during the pandemic when it became very clear how much students and teachers are struggling with converting their experience into online platforms. And so we are trying to just bring better workflows, more efficiency into that. And right now we’re starting with email, but we’ll be expanding to other things in the future.

Corey: I am absolutely the wrong person to ask about a lot of this stuff, just because my academic background, tortured doesn’t really begin to cover it. I handle academia about as well as I handled working for other people. My academic and professional careers before I started this place were basically a patchwork of nonsense and trying to pretend I was something other than I was. You, on the other hand, have very much been someone who’s legitimate as far as what you do and how you do it. Before Unicycle, you were the Director of Engineering at Wildbit, which is a name I keep hearing about and a bunch of odd places. What did you do there?

Amy: [laugh]. I will have to follow up and ask what the odd places are but—so I was leading a team there of engineers that were fully distributed across the US and also in Europe. And we were building an email product called Postmark, which some of your listeners might use, and then also a couple of other smaller things like People-First Jobs and Beanstalk—not AWS’s Beanstalk, but a developer repository and workflow tool.

Corey: Forget my listeners for a minute; I use Postmark. That’s where I keep seeing you on the invoices because it’s different branding. As someone who has The Duckbill Group, but also the Last Week in AWS things, it’s the brand confusion problem is very real. That does it. Sorry. Thank you for collapsing the waveform on that one. And of course, before that you were at PagerDuty, which is a company that most folks in the ops space are aware of, founded to combat the engineer’s true enemy: sleep.

Amy: Absolutely. It’s the product that engineers love to hate, but also can’t live without, to some degree. Or maybe they want to live without it, but uh… [laugh] are not able to.

Corey: So, I have a standing policy on this show of not talking to folks who are not wildly over-represented—as I am—and effectively disregarding the awesome stuff that they’ve done professionally in favor of instead talking about, “Wow, what’s it like not to be a white guy in the room? I can’t even imagine such a thing. It sounds hard.” However, in your case, an awful lot of the work you have done and are most proud of centers around DEI, diversity, equity, and inclusion. Tell me about that.

Amy: Absolutely. I would say that it’s the work that I’ve spent my time focusing on in recent years, but also that I’m still learning, right, and as someone who is Asian American, and also from a middle-class socioeconomic background, I have a bunch of privileges that I still have to unpack and that show up in the way that I work every day, as well. And so just acknowledging that, you know, while I spend a lot of time on DEI, still have just barely scratched the surface on it, really, in the grand scheme of things. But what I will say is that, you know, I’ve been really fortunate in my career in that I started in tech 15 or so years ago, and I started at a time when it wasn’t super hard for someone who has no CS degree to actually get into some sort of coding job. And so I fell into my first role; I was building HTML and CSS landing pages for a marketing team, for an ISP that was based in San Francisco.

So, I was cobbling together a bunch of technical skills, and I got better and better. And then I reached this point in my career where I didn’t really have a lot of mentors, and so I was like, “I don’t know what’s next for me.” But then I am also frustrated that it is so hard for our team to get things done. And so I took it upon myself to figure out Scrum and project management type of stuff for my team, and then made the jump into people management from there. So, people management and leadership through project management.

But when I look back on my career, I think about, “Oh, if I had a mentor, would that still have been my fate? Would I have continued down this track of becoming a very senior technical person and just doing that for my whole career?” Because letting go of the code was definitely a hard, hard thing. And I was lucky enough that I really did enjoy the people and the process side of all of this. And so [laugh] this relates to DEI in the fact that there’s research and everything that backs this up, but that women and women of color generally tend to get less mentorship overall and get less actionable feedback about their job performance.

And you think about how that potentially compounds over time, over the course of someone’s career and that may be one of the reasons why women and people of color get pushed out of tech because they’re not getting the support that they need, potentially. They’re not getting feedback, they’re not being advocated for in meetings, and then there’s also all the stuff that you can add on around microaggressions, or just aggressions period, potentially, depending on the culture of the team that you’re working on. And so all of those things compounded are the types of things that I think about now when I reflect on my own career and the types of teams that I want to be building in the future.

Corey: Back when I was stumbling my way through piecing my career together. I mean, as mentioned, I don’t have a degree; I don’t have a high school diploma, as it turns out, and—that was a surprise when I discovered midway through my 20s that the school I had graduated from wasn’t accredited—but I would tell stories, and I found ways to weasel my way through and I gave a talk right around 2015 or 2016, about, “Weasel Your Way to the Top: How to Handle a Job Interview,” and looking back, I would never give that talk again. I canceled it as soon as someone pointed out something that was only obvious in hindsight, that the talk was built out of things that had worked for me. And it’s easy to sit here and say that, well, I had to work for what I have; none of this was handed to me. And there’s an element of truth to that, except for the part where there was nothing fighting against me as I went.

There was not this headwind of a presumed need for me to have to prove myself; I am presumed competent. I sometimes say that as a white guy in tech, my failure mode is a board seat and a book deal, and it’s not that far from wrong. It takes, I guess, a lot of listening and a lot of interaction with folks from wildly different backgrounds before you start to see some of these things. It takes time. So, if you’re listening to this, and you aren’t necessarily convinced that this might be real or whatnot, talk less, listen more. There are a lot of stories out there in the world that I think that it’s not my place to tell but listen. That’s how I approach it.

What’s interesting about your pathway into management is it’s almost the exact opposite of mine, where I was craving novelty, and okay, I wanted to try and managing a team of people. Years later, in hindsight—I’m not a good manager and I know that about myself, and I explicitly go out of my way these days to avoid managing people wherever possible, for a variety of reasons, but at the time, I didn’t know. I didn’t know that. I wanted to see how it went.

First, I had to disabuse myself of this notion that, oh, management is a promotion. It’s not. It’s an orthogonal skill.

Amy: Yes.

Corey: The thing I really learning—management or not—now, is that the higher in the hierarchy you rise, if you want to view it that way, the less hands-on work you do, which means everything that you are responsible for that—and oh, you are responsible—isn’t something you can jump in and do yourself. You can only impact the outcome via influence. And that was a hard lesson to learn.

Amy: Right. And there are some schools of thought, though, where you can affect the outcome by control. And that’s not what I’m about. I think I’m more aligned with what you’re saying in terms of, it’s really the influence and the ability to clear the way for people who are smarter than you to do the things that they need to do. Just get out of their way, and remove the roadblocks, and just help give them what they need. That’s really, sort of like, my overall approach. But I know that there are some folks out there who lead the opposite way of, “It’s my way, and I’m going to dictate how things should be done, and really you’re here to take and follow orders.”

Corey: It’s always fun interviewing people to manage teams. “So, why do you want to be a manager?” It’s, “Oh, I want to tell people what to do.” And I have to say that as an interviewer, there is nothing that takes the pressure off nearly as well as a perfectly wrong answer. And, yes, that at least to my world, is a perfectly wrong answer to this. There aren’t that many pass-fail questions, but you can fail any question if you try hard enough.

Amy: [laugh]. Oh, gosh, yeah, it’s true. But also, at the same time, I would say that there are organizations that are built that way. Because—all it takes is the one person who wants to tell people what to do, and then they start a company, and then they hire other people who want to tell people what to do. And so there are ways where organizations like that exist and come into being even today, I would say.

Corey: The question that I have for you about engineering leadership is, back when I was an engineer, and thinking, all right, it’s time for me to go ahead and try being a manager—let’s be clear, I joke about it, but the actual reason I wanted to try my hand at management was that I found people problems more interesting than computer problems at that point. I still do, but these days, especially when it comes to, you know, cloud services marketing and such, yeah, generally, the technical problems are, in fact, people problems at their core. But talking to my manager friends of how do I go and transition from being an engineer into being a manager, the universal response I got at the time was, “Ehh, I don’t know.” Every person I knew who’d had made that transition was in the right place at the right time, and quote-unquote, “Got lucky.”

Amy: Absolutely.

Corey: And then once they had management on their resume, then they could go and transition back to being an IC and then to management again. But it’s that initial breakthrough that becomes a challenge.

Amy: Absolutely. And I fell into it as well. I mean, I got into it, partially for selfish reasons because I was, an IC, I was doing development work, and I was frustrated, and I had teammates who were coming to me and they were frustrated about how hard it was for us to get our work done, or the friction involved in shipping code. And so I took it upon myself to say, “I think I see a pattern about why this is happening, and so I will try to solve this problem for the team.” And so that’s where the Agile and Scrum thing come in, and the project management side.

And then, when I was at this company—this was One Kings Lane; this was, like, the heyday of flash sales websites and stuff like that, so it was kind of a rocket ship at that time—and because we were also growing so fast and I was interviewing folks as well, I just fell into this management role of, “Well, if I’m interviewing these people, then I guess I should be [laugh] managing them, too.” And that happens for so many people, similar stories of getting into management. And I think that’s where it starts to go wrong for a lot of organizations because, like you said, it’s not an up-leveling; it’s a changing of your role, and it requires training and learning and figuring out how to be effective as a manager. And a lot of people just stumble their way through it and make a lot of mistakes—myself included—through that process.

And that becomes really troubling knowing that you can make these really big mistakes, but these mistakes that you make don’t affect just yourself. It’s the careers of the people that you manage as well and sort of where they’re headed in their lives. And so it’s troubling to think that most leaders that are out there today have not received any sort of training on how to be a good manager and how to be effective as a manager.

Corey: I would agree with that wholeheartedly. It seems that in many cases, companies take the best engineer that they have on their team and promote them to manager. It’s brilliant in some respects in just how short-sighted it is. You are taking a great engineer and trading them for a junior and unproven manager, and hoping for the best. And there is no training on any of these things, at least—

Amy: Right.

Corey: —not the companies that I ever worked at. Of course, there are ways you can learn to be a better manager; there are people who specialize in exactly this. There are companies that do exactly this. But tech has this weird thing where it just tries to solve itself from first principles rather than believing for a minute that someone might possibly have prior experience that could be useful for these things. And—

Amy: Absolutely.

Corey: —that was a challenge. I had a lot of terrible managers before I entered management myself, and I figured, ah, I’ll do the naive thing and I’m just going to manage based upon doing the exact opposite of what those terrible managers all did. And I got surprisingly far with it, on some level. But you don’t see the whole picture when you’re an individual contributor who’s writing code—crappy in my case—most of the time, and then only seeing the aspects of your manager that they allow you to see. They don’t share—if they’re any good—the constraints that they have to deal with, that they’re managing expectations around the team, conflicting priorities, strategic objectives, et cetera because it’s not something that gets shown to folks. So—

Amy: Absolutely.

Corey: —if you bias for that, in my experience you become an empathetic manager to the people on your team, but completely ineffective at managing laterally or upwards.

Amy: Mm-hm, absolutely. And you know, I’m exploring this idea of further. Being at a very small company, I think allows me to do that. And exploring this idea of, does it have to be that way? Can you be transparent about what the constraints are as a leader while still caring for your team and supporting them in the ways that they need and helping them grow their careers and just being open about one of the challenges that you have in building the company?

And I don’t know, I feel like I have some things to prove there, but I think it’s possible to achieve some sort of balance there, something better or more beyond just what exists now of having that entire leadership layer typically be very opaque and just very unclear why certain decisions are made.

Corey: The hard part that extends that these to me beyond that is it’s difficult to get meaningful feedback, on some level, when you’re suddenly thrust into that position. I also, in hindsight, realize that an awful lot of those terrible managers that I had weren’t nearly as terrible as I thought they were. I will say that being on the other side of that divide definitely breeds empathy. Now that I’m the co-owner of The Duckbill Group, and we’re building out a leadership team and the rest, hiring managers of managers is starting to be the sort of thing that I have to think about.

It’s effectively, how do I avoid inadvertently doing end-runs around people? And oh, I’m just going to completely undermine a manager by reaching out to one of their team and retasking them on something because obviously whatever I have in mind is much more important. What could they possibly be working on that’s better than the Twitter shitpost I’m borrowing them to help out with? Yeah, you learn a lot by getting it wrong, and there becomes a power imbalance that even if you try your best to ignore it—which you should not—I assure you, the person who has less power in that relationship cannot set that aside. Even when I have worked with people I consider close friends, that friendship gained some distance during the duration of their employment because there has to be that professional level of separation. It’s a hard thing to learn.

Amy: It’s a very hard line to walk in terms of recognizing the power that you have over someone’s career and the power over, you know, making decisions for them and for the team and for the company, and still being empathetic towards their personal needs. And if they’re going through a tough time, but then you also know from a business perspective that X, Y, or Z needs to happen, and how do you push but not push too hard, and try to balance needs of people who are humans and have things that happen and go on sometimes, and the fact that we work in a capitalist society and we still need to make money to make the business run. And that’s definitely one of the hardest things to learn, and I am still learning. I definitely don’t have that figured out, but I err on the side of, let’s listen to what people are saying because ultimately, I’m not going to be the one to write the code. I haven’t done that in years, and also I would probably suck at it now. And so it behooves leaders to listen to the people who were doing the work and to try, to the best of their abilities in whatever role whether that’s exec-level leadership or mid-level… sort of like, middle management type of stuff to do what is in your power to help set them up to succeed.

Corey: I want to get back a little bit to the idea of building diverse teams. It’s something that you spend an inordinate amount of time and effort on. I do too. It’s one of those areas where it’s almost fraught to talk about it because I don’t want to sound like I’m breaking my arm by patting myself on the back here. I certainly have a hell of a lot to learn, and mostly—and I’m ashamed to admit this—I very often learn only by really putting my foot in it sometimes. And it’s painful, but that is, I think, a necessary prerequisite for growth. From your perspective, what is the most challenging part of building diverse teams?

Amy: I think it’s that piece that you said of making the mistakes or just putting yourself in a position where you are going to be uncomfortable. And I think that a lot of organizations that I’ve been in talk about DEI on a very surface level in terms of, “Oh, well, you know, we want to have more candidates from diverse backgrounds in our pipelines for hiring,” and things like that. But then not really just thinking about, but how do we work as a team in a way that potentially makes retention of those folks a lot harder? And for myself, I would say that when I was earlier on in all of this in my learning, I would say that I was able to kickstart my learning by thinking about my own identity, the fact that I was often the only Asian person on my team, the only woman on my team, and then more recently, the only mom on my team. And that has happened to me so many times in my career. More often than not.

And so being able to draw on those experiences and those feelings of oh, okay, no one wants to hear about my kid because everyone else is, you know, busy going out to drink or something on the weekends. And like that feeling of, you know, that not belonging, and feeling of feeling excluded from things, and then thinking about how then this might manifest for folks with different identities for myself. And then going there and learning about it, listening, doing more listening than talking, and yeah, and that’s, that’s really just been the hardest part of just removing myself from that equation and just listening to the experiences of other people. And it’s uncomfortable. And I think a lot of people are—you have to be in the right mindset, I guess, to be uncomfortable; you have to be willing to accept that you will be uncomfortable. And I think a lot of folks maybe are not ready to do that on a personal level.

Corey: The thing that galls me the most is I do try on these things, and I get it wrong a fair bit. And my mistakes I find personally embarrassing, and I strive not to repeat them. But then I look around the industry—and let’s be clear, a lot of this is filtered through the unhealthy amount of time I spend on Twitter—but it seems that I’m trying and I’m failing and attempting to do better as I go, and then I see people who are just, “Nope. Not at all. In fact, we’re not just going to lean into bias, we’re going to build a startup around it.”

And I look at this and it’s at some level hard to reconcile the fact that… at first, that I’m doing badly at all, which is the easy cop-out of, “Oh, well, if that is considered acceptable on some level, then I certainly don’t even have to try,” which I think is a fallacy. But further it’s—I have to step beyond myself on that and just, I cannot fathom how discouraging that must be, particularly to people who are early in their careers because it looks like it’s just a normal thing that everyone thinks and does that just someone got a little too loud with it. And it’s abhorrent. And if people are listening to this and thinking that is somehow just entrenched, and normalized, and everyone secretly thinks that… no. I assure you it is not something that is acceptable, even in the quote-unquote, “Private white dude who started companies” gathering holes. Yeah, people articulating sentiments like that suddenly find themselves not welcome there anymore, at least in every one of those types of environments I’ve ever found myself in.

Amy: Yeah, the landscape is shifting. It’s slow, but it is shifting. And, myself on Twitter, like, I do a lot of rant-y stuff too sometimes, but despite all of that, I feel like I am ultimately an optimist because I have to be. Otherwise, I would have left tech already because every time I am faced with a job search for myself, I’m like, “Should I—is this it? Am I done in tech? Do I want to go do something else? Am I going to finally go open that bakery that I’ve always wanted to open?” [laugh].

And so… I have to be an optimist. And I see that—even in the most recent job search I’ve done—have seen so many new founders and new CEOs, really, with this mindset of, “We want to build a diverse team, but we’re also doing it—and we’re using diversity as a foundation for what we want to build; it’s part of our decision-making process and this is how we’re going to hold ourselves accountable to it.” And so it is shifting, and while there are those bad actors out there still, I’m seeing a lot of good in the industry now. And so that’s why I stick around; that’s why I’m still here.

Corey: I want to actually call something out as concrete here because it’s easy for me to fall into the trope of just saying vague things. I’ll be specific about something, give us a good example. We’ve done a decent job, I think, of hiring a diverse team, but—and this is a problem that I see spread across an awful lot of companies—as you look at the leadership team, it gets a lot wider and a lot more male. And that is an inherent challenge. In our particular case, my business partner is someone who I’ve been close friends with for a decade.

I would not be able to start a business with someone I didn’t have that kind of relationship with just because your values have to be aligned or there’s trouble down the road. And beyond that, it winds up rapidly, on some level, turning into what appears to be a selection bias. When you’re trying to hire senior leaders, for example, there’s a prerequisite to being a senior leader, which is embodied in the word senior, which implies tenure of having spent a fair bit of time in an industry that is remarkably unfriendly in a lot of different ways to a lot of different people. So, there’s a prerequisite of being willing to tolerate the shit for as long as it takes to get to that level of seniority, rather than realizing at any point as any of us can, there are easier jobs that don’t have this toxicity inherent to them and I’ll go do that instead. So, there’s a tenure question; there’s a survivorship bias question.

And I don’t have the answers to any of this, but it’s something that I’m seeing, and it’s one of those once you see it, you can’t unsee it any more moments. At least for me.

Amy: Yeah, absolutely.

Corey: Please tell me I’m not the only person who see [laugh]—who is encountering these problems. Like, “Wow, you just sound terrible.” Which might very well be a fair rejoinder here. I’m just trying to wrap my head around how to think about this properly.

Amy: Yeah. I mean, this is why I was saying that I am very optimistic about [laugh] new companies that are coming—like, up-and-coming these days, new startups, primarily, because you’re right that a lot of people just end up quitting tech before they get to that point of experience and seniority, to get into leadership. I mean, obviously, there’s a lot of bias and discrimination that happens at those leadership levels, too, but I will say that, you know, it’s both of those things. There are also more things on top of that. But this is why I’m like, so excited to see people from diverse backgrounds as founders of new companies and why I think that being able to be in a position to potentially either help fund, or advocate, or sponsor, or amplify those types of orgs, I think is where the future is that because ultimately, I think a lot of the established companies that are out there these days, it’s going to be really hard for them to walk back on what their leadership team looks like now, especially if it is a sizable leadership team and they’re all white men.

Corey: Yeah. I’m going to choose to believe we say sizable leadership team that it’s also not—we’re talking about the horizontal scaling that happens to some of us, especially during a pandemic as we continue to grow into our seats. You’re right, it’s a problem as well, where you can cut a bit of slack in some cases to small teams. It’s, “Okay, we don’t have any Black employees, but we’re three people,” is a lot more understandable-slash-relatable than, “We haven’t hired any Black people yet and we’re 3000 people.” One of those is acceptable—or at least understandable, if not acceptable—the other is just completely egregious.

Amy: Yes. And I think then the question that you have to ask if you’re looking at, you know, a three-person company, or [laugh] I guess, like in my case, I was looking at the seven-person company, is that, “Okay. There are currently no Black people on your team. And why is that?” And then, “What are you doing to change that? And how are you going to make sure that you’re holding ourselves accountable to it?”

Because I think it’s easy to say, “Oh, you know, the first couple of hires were people we just worked with in the past, and they just happened to, you know, look like us and whatnot.” And then you blink becau—and you do that a handful of times, and you blink, and then suddenly you have a team of 25 and there are no people of color on your team. And maybe you have, like, one woman on the team or something. And you’re like, “Huh. That’s strange. I guess we should think about this and figure out what we can do.”

And then I think what ends up happening at that point is that there are so many already established behaviors, and cultural norms, and things like that, that have organically grown within a team that are potentially not welcoming towards people from different backgrounds who have different backgrounds. So, you go and attempt to hire someone who is different, and they come in, and they’re just sort of like, “This is how you work? I don’t feel like I belong here.” And then they don’t stay, and then they leave. And then people sit there and scratch their heads like, “Oh, what did we do wrong?” And, “I don’t get it.”

And so there’s this conversation, I think, in the industry of like, “Oh, it’s a pipeline problem, and if we were just able to hire a lot of people from diverse backgrounds, the problem is solved.” Which really isn’t the case because once people are there and at your company, are they getting promoted at the same rate as white men? Are they staying with the company for as long? And who’s in leadership? And how are you working to break down the biases that you may have?

All those sorts of things, I think, generally are not considered as part of all of this DEI work. Especially when, in my experience in startups, the operational side of all that is so immature a lot of the times, just not well developed that deeper thought process and reflection doesn’t really happen.

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Corey: I do my best to have these conversations in public as frequently as is practical for me to do, just because I admit, I get things wrong. I say things that are wrong and I’m doing a fair bit of learning in public around an awful lot of that. Because frankly, I can withstand the heat, if it comes down to someone on Twitter gets incredibly incensed by something I’ve said on this podcast, for example. Because it isn’t coming from a place of ill intent when someone accuses me of being ableist or expressing bias. My response is generally to suppress the initial instinctive flash of defensiveness and listen and ask.

And that is, even if I don’t necessarily agree with what they’re saying after reflection, I have to appreciate on some level the risk-taking inherent in calling someone out who is in my position where, if I were a trash fire, I could use the platform to turn it into, “All right. Now, let’s go hound the person that called me out.” No. I don’t do that, full stop. If I’m going to harass people, it’s going to be—not people, despite what the Supreme Court might tell us—but it’s going to be a $2 trillion company—one in particular—because that’s who I am and that’s how I roll.

Whenever I get a DM—which I leave open because I have the privilege to do that—from folks who are early career who are not wildly over-represented, I just have to stop and marvel for a minute at the level of risk-taking inherent to that because there is risk to that. For me, when I DM people, the only risk I feel like I’m running at any given point is, “Are they going to think that I’m bothering them? Oh, the hell with it. I’m adorable. They’ll love me.” And the fact that I’m usually right is completely irrelevant to that. There’s just that sense of I don’t really risk a damn thing in the grand scheme of things compared to the risk that many people are taking just living who they are.

Amy: Yeah. And someone DMs you and you suppress that initial sort of defensiveness: I would say that that is an underrated skill. [laugh].

Corey: Well, a DM is a privilege, too. A call in—

Amy: Yes.

Corey: —is deeply appreciated; no one owes it to me. I often will get people calling me out on Twitter and I generally stop and think about that; I have a very close circle of friends who I trust to be objective on these things, and I’ll ask them, “Did I get this wrong?” And very often the answer is yes. And, “Well, I thought the joke was funny and I spent time building it.” “Yeah, but if people hear a joke I’m making and feel bad about it, then is it really that good of a joke or should I try harder?” It’s a process, and I look back at who I was ten years ago and I feel a sense of shame. And I believe that if anyone these days doesn’t, either they were effectively a saint, or they haven’t grown.

Amy: Yes.

Corey: And that’s my personal philosophy on this stuff, anyway.

Amy: Yeah, absolutely. And that growth is so important. And part of that growth really is being able to suppress your desire to make it about you, [laugh] right? That initial, “Oh, I did something bad,” or, “I’m a horrible person because I said this thing,” right? It’s not about you, there’s, like, the impact that you had on someone else.

And I’ve been giving this some thought recently, and I—you know, I also similarly have a group of trusted friends who I often talk about these things with, and you know, we always kind of check ourselves in terms of, did we mess something up? Did we, you know, put our foot in our mouths? Stuff like that. And think what it really comes down to is being able to say, “Maybe I did something wrong and I need to suppress that desire to become defensive and put up walls and guard and protect myself from feeling vulnerable, in order to actually learn and grow from this experience.”

Corey: It’s hard to do, but it’s required because I—

Amy: Extremely, yes.

Corey: —used to worry about, “Ohh, what if I get quote-unquote, ‘canceled?’” well, I’ve done a little digging into this and every notable instance of this I can find is when someone is called out for something crappy, they get defensive, and they double-down and triple-down and quadruple-down, and they keep digging a hole nice and deep to the point where no one with a soul can really be on their side of this issue, and now they have a problem. I have never gotten to that point because let’s be honest with you, there are remarkably few things I care that passionately about that I’m going to pick those fights publicly. The ones that I do, I am very much on the other side [laugh] of those issues. That has not been a realistic concern.

I used to warn every person here before I hired them—to get this back to engineering management—that there was a risk that I could have a bad tweet and we don’t have a company anymore. I don’t give that warning anymore because I no longer believe that it’s true.

Amy: Mm-hm. Mm-hm. I also wonder about, in general, because of the world that we live in, and our history with white supremacy and oppression and all those things, I also wonder if this skill of being able to self-reflect and be uncomfortable and manage your own reaction and your emotions, I wonder if that’s just a thing that white people generally haven’t had a lot of practice for because of the inherent privileges that are afforded to white people. I wonder if a lot of this just stems from the fact that white people get to navigate this world and not get called out, and thus don’t have this opportunity to exercise this skill of holding on to that and listening more than talking.

Corey: Absolutely agree. And it gets piled on by a lot of folks, for example—I’ll continue to use myself as an example in this case—I live in San Francisco. I would argue that I’m probably not, “In tech,” quote-unquote, the way that I once was, but I’m close enough that there’s no discernible difference. And my social circle is as well. Back before I entered tech, I did a bunch of interesting jobs, telemarketing to pay the bills, I was a recruiter for a while, I worked construction a couple of summers.

These days, everyone that I engage with for meaningful periods of time is more or less fairly tech adjacent. It really turns into a one-sided perspective. And I can sit here and talk about what folks who are not living in the tech bubble should be doing or how they should think about this, but it’s incredibly condescending, it’s incredibly short-sighted, and fails to appreciate a very different lived experience. And I can remind myself of this now, but that lack of diversity and experience is absolutely something where it feels like the tech bubble, especially for those folks in this bubble who look a lot like me, it is easy to fall into a pattern of viewing ourselves as the modern aristocracy where we deserve the nice things that we have, and the rest. And that’s a toxic pattern. It takes vigilance to avoid it. I’m not saying I get it right all the time, by a landslide, but ugh, the perils of not doing that are awful.

Amy: Agreed. And it shows up, you know, getting back to the engineering manager and leadership and org building piece of things, that shows up even in the way that we talk about career development and career ladders, for those of us in tech, and software engineering specifically for me, where we’ve kind of like come up with all these matrices of job levels, and competencies, all that, and humans just are so vastly different. Every person is an individual, and yet we talked about career ladders and how to advance your career in this two-dimensional matrix. And, like, how does that actually work, right?

And I’ve seen some good career ladders that account for a larger variety of competencies than just, “Can you code?” And, “What are your system design skills?” And, “Do you understand distributed systems?” And so on and so forth, but I think a lot gets left behind and gets left on the table when it comes to thinking about the fact that when you get a group of people together working on some sort of common cause or a product, that there’s so much more to the dynamic than just the writing of the code. It’s how do you work with each other? How do you support each other? How do you communicate with each other? And then all my glue work—that is what I call it—like, the glue work that goes into a successful team and building products, a lot of that is just not captured in the way that we talk about career development for folks. And it’s just incredibly two-dimensional, I think.

Corey: One last question that I have for you before we wrap the episode here is, you spend a lot of time focusing on this, and I have some answers, but I’m very interested to hear yours instead because I assure you, the world hears enough from me and people who look like me, what is the biggest mistake that you see companies making in their attempts to build diverse teams?

Amy: I would say that there’s two major things. One is that there have been a lot of orgs in my own past that think about diversity, equity, inclusion as a program and not a mindset that everyone should be embracing. And that manifests itself into, sort of like, this secondary problem of stopping at the D part of D, E, and I. That’s the whole, “We’re going to hire a bunch of people from different backgrounds and then just we’re going to stop with that because we’ve solved the problem.” But by not adopting that mindset of the equity, the inclusion, and also the welcoming and the belonging piece of things internally, then anyone that you hire who comes in from those marginalized or minority backgrounds is not going to want to stay long-term because they don’t feel like they fit in, they don’t feel like they belong.

And so, it becomes this revolving door of you hire in people and then those people leave after some amount of time because they’re not getting what they need out of either the role or for themselves personally in terms of just emotional support, even. And so I would say that’s the problem that I see is not a numbers game—although the metrics and the numbers help hold you accountable—but the metrics and the numbers are not the end goal. The end goal is really around the mindset that you have in building the org and the way that people behave. And the way that you work together is really core to that.

Corey: What I tend to see on the other side is the early intake funnels. People will reach out to me sometimes, “Hey, do you know any diverse speakers we can hire to do a speaking engagement here?” It doesn’t… work that way. There’s a lot more to it than that. It is not about finding people who check boxes, it is not about quote-unquote, “Diversity hires.”

It’s about—at least in my experience—structuring job ads, for example, in ways that are not coded—unconsciously in most cases, but ehh—that are going to resonate towards folks who are in certain cultures and not in others. It’s about being more equitable. It’s about understanding that not everyone is going to come across in a job interview as the most confident person in the room. Part of the talk that I gave on how to handle job interviews, there was a strong section in it on salary negotiation. Well, turns out when I do it, I’m an aggressive hard-charger and they like that, whereas if someone who is not male does that, well, in that case, they look like they’re being difficult and argumentative and pushy and rising above their station. It was awful.

One of the topics I’m most proud of was the redone version of that talk that I gave with a friend, Sonia Gupta, who has since left tech because of how shitty it is, and that was a much better talk. She was a former attorney who had spent time negotiating in much higher-stakes situations.

Amy: Yeah.

Corey: And it was terrific to see during the deconstruction and rebuilding of that talk, just how much of my own unconscious bias had crept in. It’s, again, I look back at the early version of those talks and I’m honestly ashamed. It wasn’t from ill will, but it’s always impact over intent as far as how this has potentially made things worse. It’s, if nothing else, if I don’t say the right things when I should speak up, that’s not great, but I always prefer that to saying things that are actively harmful. So—

Amy: Absolutely.

Corey: —it’s hard. I deserve no sympathy for this, to be clear. It is incumbent upon all of us because again, as mentioned, my failure mode is a non-issue in the world compared to the failure mode for folks for against whom the deck has been stacked unfairly for a very long time. At least, that’s how I see it.

Amy: Right. And that’s why I think that it’s important for folks who are in positions of power to really reflect on—even operationally, right, you were mentioning your job ads, and how to structure that to include more inclusive language, and just doing that for everything, really, in the way that you work. How do decisions get made? And by whom? And why? How do you structure things like compensation? Even, like, how do you do project planning, right?

Even in my own reflections, now when I think back towards Scrum and Agile and all of that, I think that the base foundation of all of that was like was good, but then ultimately the implementation of how that works at most companies is problematic in a lot of ways as well. And then to just be able to reflect and really think about all of your processes or policies—all of that—and bring that lens of equity, really, equity and inclusion to those things, and to really dig deep and think about how those things might manifest and affect people from different backgrounds in different ways.

Corey: So, before we wrap, something that I think you… are something of an empathetic party on is when I see companies in the space who are doing significant DE&I initiatives, it seems like it’s all flash; it feels like it’s all sizzle, no steak to appropriate a phrase from the country of Texas. Is that something that you see, too?

Amy: I do think that it is pretty common, and I think it’s because that’s… that’s the easy route. That’s the easy way to do it because the vanity metrics, and the photo of the team that is so diverse, and all these things that show up on a marketing website. I mean, there—it’s, like, a signal for someone, potentially, who might be considering a job at your company, but ultimately the hard work that I feel like is not happening is really in that whole reflecting on the way you do business, reflecting on the way that you work. That is the hard work and it requires a leadership team to prioritize it, and to make time for it, and to make it really a core principle of the way that you build an org., and it doesn’t happen enough, by far, in my opinion.

Corey: It feels like it’s an old trope of the company that makes a $100,000 donation and then spends $10 million dollars telling the world about it, on some level. It’s about, “Oh, look at us, we’re doing good things,” as opposed to buckling down and doing the work. Then the actual work falls to folks who are themselves not overrepresented as unpaid emotional labor, and then when the company still struggles with diversity issues, those people catch the blame. It’s frustrating.

Amy: Yeah. And as an organization, if you have the money to donate somewhere, that’s great, but it can’t just stop at that. And a lot of companies will just stop at that because it’s the optics of, “Oh, well, we spent x millions of dollars and we’ve helped out this nonprofit or this charity or whatnot.” Which is great that you’re able to do that, but that can’t be it because then ultimately, what you have internally and within your own company doesn’t improve for people from those backgrounds.

Corey: I want to thank you for taking so much time to chat with me about these things. Some of these topics are challenging to talk about and finding the right forum can be difficult, and I’m just deeply appreciative that you were able to clear enough time to have that chat with me today.

Amy: Yeah, thank you for having me. I mean, I think it’s important for us to recognize, even between the two of us that, I mean, obviously, you as a white man have benefited a lot in this space, and then even myself as, you know, that model minority whole thing, but growing up very adjacent to white people and just being ingrained in that culture and raised in that culture, you know, that we have those privileges and there’s still parts of the conversation, I think, that are not captured by [laugh] by the two of us are the nuances as well, and so just recognizing that. And it’s just a learning process. And I think that everyone could benefit from just realizing that you’ll never know everything. And there’s always going to be something to learn in all of this. And yes, it is hard, but it’s something that is worthwhile to strive for.

Corey: Most things worthwhile are. If people want to learn more about who you are, how you think about these things, potentially consider working with you, et cetera. Where can they find you?

Amy: So, I am on Twitter. I am the queen of very, very long threads, I should just start a blog or something, but I have not. But in any case, I’m on Twitter. I am AmyChanta, so @A-M-Y-C-H-A-N-T-A.

Our website is unicycle.co, if you’re thinking about applying for a role, and working with me, that would be awesome. Or just, you know, reach out. I’d also just love to network with anyone, even if there’s not an open position now. I just, you know, build that relationship and maybe there will be in the future. Or if not at Unicycle, then somewhere else.

Corey: And we will, of course, put links to that in the [show notes 00:48:13]. Thank you so much, once again. I appreciate your time.

Amy: Thanks for having me.

Corey: Amy Chantasirivisal, Director of Engineering at Unicycle. I’m Cloud Economist Corey Quinn and this is Screaming in the Cloud. If you’ve enjoyed this podcast, please leave a five-star review on your podcast platform of choice, whereas if you’ve hated this podcast, please leave a five-star review on your podcast platform of choice along with a comment pointing out that it’s not about making an MVP of a bicycle that turns into a unicycle so much as it is work-life balance.

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