When To Speak Up

About this Episode

The episode opens with Mike sharing two formative stories that highlight the importance of speaking up against inappropriate behavior. The first story recounts a moment in the late 1990s when a manager made a blatantly racist comment during a hiring discussion, leaving Mike stunned and regretful for not speaking out. The second story contrasts that moment with a more positive example—Jonathan Schwartz, then a Sun Microsystems executive, swiftly and calmly shutting down a sexist remark during a public tech event. These stories set the stage for a broader discussion on moral courage, preparation, and the power of speaking up in professional settings.

The panel—Mike, Will, Justin, Kyle, and Tim—then share personal anecdotes ranging from experiences with crass coworkers to moral gray areas in technical and corporate decision-making. Justin recounts a story of an inappropriate joke at a company meeting and the swift exit of the offending employee, highlighting the importance of understanding professional boundaries. Will reflects on his past confrontations, including a fiery exchange with Alan Kay and a more recent situation where he lost a technical argument at work but chose to “disagree and commit” to preserve team cohesion. Tim and others emphasize how reading the room, respecting legal and ethical boundaries, and choosing the right hills to die on are essential strategies for navigating workplace culture.

The conversation closes with strategies to foster healthy debate and encourage junior team members to voice their thoughts. The group stresses the importance of frameworks like DACI for decision-making, teaching engineers to argue both sides of an issue, and maintaining psychological safety in teams. Ultimately, the takeaway is that speaking up—whether against clear misconduct or in nuanced technical debates—requires preparation, emotional intelligence, and humility. And sometimes, the bravest choice is knowing when to push, when to let go, and when to walk away.

Transcript:

 MIKE: Hello and welcome to another episode of the Acima Development Podcast. I’m Mike, and I'm hosting today. Today, I've got with me Tim, joining us from security. We've got Will Archer, as is usually joining us. Thank you, Will. We've got Kyle, and we've got Justin. We've got a great panel here, and we've got a good topic.

I've been bouncing this one around for a while. I'm excited to talk about it. And I'm going to start with a couple of stories about...well, I was present for both of them. One of them is more about me, and one is more about somebody else. The context for the first one...and let's start by making this a little awkward. So, I'm a white guy [laughs].

WILL: Oh no.

JUSTIN: No, no.

[laughter]

MIKE: So, my dad's family's mostly British. My mom is an immigrant from Norway. So, white guy, right? This...value-neutral on that one, but it affects what comes next. So, I lived in Louisiana back in the late ‘90s, and I was working at a construction company, upholstery [inaudible 01:24], an interior construction company. So, we’d work in office buildings, so we’d tear out the previous setup. When one tenant moved out, another tenant moved in. It's not all we did, but it's a lot of what we did, and it worked.

I was working in the warehouse as a warehouse manager at the time. So, I was downstairs. People would walk in and ask for a job sometimes, and I couldn't make the choice. I'd refer them to the manager who worked upstairs in the offices. So, I was sitting at my desk one day and somebody walks in, asked for a job. So, I called upstairs [chuckles] to my manager upstairs who could make this decision. And his response was, “Are they white or black?”

And I was so flummoxed [laughs]. I couldn't believe that he'd said that. I was just so floored. I just stared at the phone [laughs]. I just stared at the phone for 20 seconds. And then, he goes on. He says, “Okay, just say W or B”. He thought the reason that I wasn't saying anything is because I was afraid of incriminating myself. So, I just stared at the phone, like, I didn't say anything else. I just stared at the phone, and, honestly, to my regret [chuckles] because I should have said something, but I had no idea what to say. I was so, so completely gobsmacked. I couldn't react. He came down.

And the race of the person who was applying doesn't really apply here, right? What matters is, I wish I would have said something. And this was going on 30 years ago, and I still think about that because I wish I had had something better to say. I wish that I had prepared ahead of time, you know, had gone through this scenario in my mind. I just had not gone through this scenario because I didn't expect somebody to say something like this, and so no good reaction. It certainly changed my perception [chuckles] of the manager upstairs, but I didn't know what to say. So, there is my first story.

Second story. I was at a Java Users Group in the early 2000s. And Jonathan, I made sure I looked this up, and Jonathan Schwartz, who later became CEO of Sun Microsystems, was coming to speak at this Java Users Group. So, there was a lot of people there, hundreds of people there probably from the Java community. And Sun Microsystems was pushing their own distribution of Linux at the time. It didn't go anywhere, by the way [laughs], and neither did Sun for that...well, they were eaten by Oracle a few years later [laughs]. But --

WILL: Solaris was all right. Solaris wasn't so bad.

MIKE: They were a meaningful company at the time. I was actually doing a little research on this before the call thinking about it. I guess they had a lot of their business in finance, and the crisis in 2008 did not serve them well [laughs].

WILL: They were pretty well cooked by then, though.

MIKE: I think they were. They were stretching a bit. Which is not really the topic of the story. I was at a Java Users Group...but, you know, it gives you a little context. I don't think he was CEO. I think he was, like, a VP at the time. But he came there, and he was representing the company certainly. And he was going to give out free copies of their new distro of Linux. So, I was like, oh, cool, the Sun distribution of Linux. And he used it...I got one, and it was, like, they hadn't even removed all the branding. I think it was SUSE Linux. They changed a little bit. But they were going to repackage and sell it.

And the person introducing Mr. Schwartz, talking about getting things started, was talking along and made just this badly sexist remark, shockingly sexist joke in front of hundreds of people, right, and thought that this would somehow be okay. And, interestingly, Jonathan Schwartz immediately shut it down. “No.” He didn't escalate it. He just, “No,” and then moved on.

And I've always been impressed with that. He clearly had prepared for that moment, and he knew if somebody said something that was out of line, he would put them in place. And this wasn't somebody who worked for him. He just had practiced this muscle that he stopped what the presenter was saying, you know, that's not okay, and then he went on. And here I am again going on 30 years later, and I remember that. I remember that because I was so impressed with how well he handled that situation. He said something, and he handled it with grace. He didn't make a big deal about it. He just made sure that's not acceptable behavior. We're going to move on.

Both of these are for very specific kind of speaking up. There's an instant, clearly something out of line. Right in the moment, say something. There are lots of other kinds of moments where maybe it's not quite so clear, right? Maybe there's a decision that is complicated, that's not quite clear. And a lot of times, there's technical decisions. Do I get involved in this? And they're hard. But I'm going to reference what I didn't do, which was prepare for that kind of situation ahead of time, and what Jonathan Schwartz clearly did do, which was think about it ahead of time, prepare, and practice so that when he was in a moment where the decision came, he was able to say the right thing at the right time.

Oh, I'm going to start by asking my panel here. What are some times that you wish you had spoken up and you didn't, and maybe sometimes, you know, maybe the opposite? You spoke up when you shouldn't have.

JUSTIN: So, I've got two instances, one that I was present at and one I was not. One I was present at. A company I worked for this guy was very, like, I worked directly with this guy, and he was very, very crass. Like, if there was a dirty joke, he knew it, and he would say it. And most of the time, like, I had known this guy for, like, you know, I was working with this guy for a couple of months. And most of the time, it was like, oh, okay, he's a decent engineer, but, man, is he crass. He's not going to last long at the company. Somebody's going to make a complaint.

Well, the next month rolls around, and they have a company meeting. There was the CTO who was a woman, and it was a meeting of the engineering department. So, there was probably, like, 30, 40 people in this room. And this guy says a joke really loudly, and it was very, very crass, something about humping somebody else, I don't know. It was really, really bad. And the room deafens, and everybody looks around. And the CTO she just starts the meeting right there. She didn't say anything to him right then, but she probably should have.

But, in any case, he was gone within two weeks. So, the next time that she flew out, it was to talk to him specifically and escort him out. So, that was a case of reading the room and understanding who you're talking to. I think that's a skillset that people need to have. It's like, understand the audience of who you're talking to.

And then, the next story I have I wasn't at, but I definitely heard about it. I work for a large bank now. They recently had a large initiative to return to office, and the CEO was having a couple of town halls to talk about it, and somebody very senior...well, not very senior, somebody who was probably two levels above me, but they were still an IC. It's basically architect-level position, super architect-level position. He asked directly to the CEO something to the effect of, you know, you do realize this is going to really ruin morale. And I don't see how this can't ruin morale.

And so, what happened next the town hall went on because the CEO didn't have a good answer for that. And what happened next was that guy's boss's boss somehow heard about that question and fired him in the elevator later that day. Then the story doesn't end there.

WILL: Ask me almost anything.

JUSTIN: Ask me almost anything [laughter]. And the guy later on got his job back.

WILL: Whoa.

JUSTIN: Because it was specifically, you know, it was an ask-anything type of situation. And the boss's boss had overstepped his authority and, well, I guess he fired him for the wrong reason, so...And that sort of --

WILL: Yeah, you better get that constructive dismissal. There are other steps. You got to make him [inaudible 11:17] and do the hokey-pokey [chuckles].

JUSTIN: So, I guess my two stories were examples of be aware of what you're speaking, and sometimes it's worth it to speak truth to power, and sometimes it's not worth it to be very crass.

WILL: Yeah. Damn, I'm taken aback at just the stories of people just being just woefully out of line. I have not had a lot of experiences with people talking like that, I mean, I don't know. I believe you guys. I know these guys are out here. I just haven't...I haven't had that experience.

For me, most of the stuff that I've been exposed to that's been really difficult has been within the bounds of professional communication, right? Like engineering teams, they're all hard problems, and very often, the solution to those problems is not immediately apparent. And you're choosing without prior foreknowledge between two equally good strategies, and that's where you see a lot of people butting heads. Although I will say I talk a lot of shit, and I've gotten better at it. I've gotten a lot better at it. But I have a ridiculous story if you guys want to hear it.

MIKE: It's story time.

WILL: When I was younger, like, when I was young, right, I was, like, 25 and I was at the University of Utah. I was at the Graduate Student Advisory Committee. So, we were a little selected group of grad students that got to sit in faculty meetings, which was a profound waste of time but very interesting. And we got to talk to, like, faculty candidates would come in and be like, “Okay, well what are the grad students like?” And we had no power. It was like a nice little pat on the head committee, but I appreciated it.

And we got to meet people. And one of the people that we got to meet when he buzzed by was very famous in certain circles, University of Utah alumnus Alan Kay, who is just a wretched, dried-up, useless, blowhard. Like, you know Alan Kay's name because, Alan Kay, for the entirety of my lifetime, has completely abandoned any form of useless work to tell the story of Alan Kay ad nauseam.

We had a lunch meeting, me and a bunch of grad students. Like, you had the privilege of interacting with diet Will, who most of his fangs have been pulled...I am so much...I'm sweetness and light. 25-year-old punk rock Will was not as retiring and diplomatic as I am now, and it did not go good. He spent...I don't even remember what we were arguing about. We were arguing about, like, operating systems, like, in the weeds of the programming languages. And I was a pretty serious, like, compiler operating systems nerd at that time in my life. I didn't have a lot of time for Smalltalk, Smalltalk the language, rather than small talk, like, chitchat. Like, we were deep in it, and Alan Kay he was ridiculous, really bad.

And it wasn't only me that he made a really poor impression on, but I'm not going to out anybody else because they had the good sense to keep their mouth shut. And he spent the rest of his lecture in front of the entire university...I got, out of a 45-minute lecture, I got about 15 minutes directed at how bad I suck. He didn't mention me by name, but everybody who knew...and there was a blast radius among my faculty advisor. And other people were just, like, Will, what did you do?

And the right thing to do is to just let the old man flap his gums at you because it doesn't matter. Oh, he sucked so bad. Sorry, I can't read Alan Kay articles anymore having interacted with the guy and seen the absolute wasteman of his professional contributions for the last 50 years. Anyway, moving on.

MIKE: So, you and Alan Kay don't get along [laughs].

WILL: There is no we [laughter]. I doubt that he has thought about me twice in the intervening 20 years. He’s probably dead now.

MIKE: That's the worst moral to take from this story [laughs]. The real moral...total sideline, Calvin and Hobbes, the greatest comic ever written, there's an arc about Snow Goons, where he builds monsters, and they go out and wreak havoc. And [chuckles] the final line of the panel...[inaudible 17:07] if it's a panel. The final strip of the arc is Calvin learning his lesson. And Hobbes asks him, “So, what did you learn from this?” He says, “Snow goons are bad news [laughs].” And Hobbes observes that he's actually learning nothing from this [laughs], and that's how he likes it.

WILL: Well, I actually think it segues into the general strategery for these sorts of disagreements, which is, at that time, I hadn't developed this muscle yet, but, like, now I've got it, and I still talk a lot of shit. But I get along pretty well with engineering organizations, even when we don't agree and I don't get my way...is when you can tell that things aren't going your way.

This conversation that I had with this rich, old fossil, who's completely high on his own supply, and he was in an orbit somewhere completely detached from the actual state of the art in 2006 or whatever, there was no reaching that guy. There was no communicating with that guy. There's no conversation we were going to have. So, just vibe out, eat my expensive, free lunch, let him ramble, and move on.

More recently, I have learned my lesson. And there was a big debate that happened a few years ago. And I was on the losing end of it, where they were getting rid of...we had this Java server, like, I work for a big retailer, like, a big retailer. We shop there. And they were getting rid of their...they had this big initiative to get rid of this Spring Boot application server, which was sort of, like, our gateway behind the firewall downstream services. They wanted to get rid of all of this old, crusty Spring Boot infrastructure and replace it with team-specific Node JS microservices, I guess you'd call it, like, gateway microservices. And every team, every functional group would have their own.

And it was a dumb idea. It was dumb. Like, why do this? Like, why...it would make it slow. Because it was based on the false premise because that was in JavaScript and many of our other systems were in JavaScript, it would make the engineers fungible across these radically different domains, which has never happened. It's two years on. It never worked. I was like, why? This is going to be slow. It's not going to buy us anything. It's going to slow down application development. You guys don't have the appetite to pay down the tech debt of moving this stuff over. So, you're going to build a new service, but you're not going to get rid of the old one. And they haven't.

MIKE: Oh [laughs].

WILL: You know? All this stuff happened, and I was right about everything. And I told them, and they said, “We don't care.” And I said, “Cool.” [laughter] Disagree and commit. Because, in the end, if I had continued paddling the boat the wrong way, we would just spin in circles. And it is an absolute guarantee that we will fail. If we can't disagree and debate and get at everything back and forth, and then we're going to say, we're going to go, and, like, we're going to go. And, as such, we did not get an optimal solution, and there have been consequences for that solution, but we are moving forward slowly.

And I still have a good reputation in the organization. I got my ‘I told you so’ points. I got to dig in a time or two privately. But I'm fine, and they're fine, and the project is fine. And was I right? Yes, I was. Were they wrong? Yes, they were. Does it matter in the end? I don't know. Maybe, maybe not. But that's how you have to deal with it. If you are on the losing team, take your L, and shut up [laughs]. And that's how it goes.

I have a friend, a good friend of mine. He got into a similar slapfight on some GraphQL implementation architecture, and he couldn't take his L. And he was a contractor, really senior guy, made a lot of money, but he was still a contractor. And contractors can be fired very cheaply, and he's gone. And when he was going to get hired back...he subsequently got hired back. He's an excellent engineer, and he has been doing great work, both before and since. But he got into this fight with a staff engineer and a director, and they got his ass. He was done. He was out of work for three months.

And when he was trying to get back, they were on the phone with a manager who was trying to bring him back on. He's like no, man, get rid of this guy. He's a jerk. Get him gone. We don't want him. You don't want this dude. And it's a fine line to walk. If you want to have a career and still talk your shit [laughs], you got to figure out how to balance it.

MIKE: Interesting. You talk about reading the room, and you say that's the key. And the room may be you and one other person. Being attentive to the person or people you're talking with is a huge amount of the communication, and that's not easy for everybody. I mean, there's people who are neurodivergent who have a really hard time with that. And so, that's going to be something you're going to have to work on and work on and work on because it matters. That's where a lot of the communication is. I think there was a ton of insight from your stories, Will.

WILL: [chuckles] Well, I've been talking shit for a long time.

[laughter]

TIM: I do think these kind of moral boundaries are a little bit endemic with the tech industry, and these companies are in a public position where it gets...like, okay, so to go back to your original story there, Mike, how you've got a kind of construction related business.

MIKE: Yes.

TIM: And I hate to say it, but it is kind of like a stereotype sometimes, you know, the street construction workers, there's a certain level of crass that just comes with that industry. In some places, it's just more publicly accepted, and that's unfortunate. And that's not at all desirable or a place where you want to work. But within the tech industry, you just go back 10 years, and there's patterns of it getting...okay, so, Uber, the bro culture in Uber with...I can't remember...there was a couple of executives that ended up getting canned because of sexual harassment and discrimination and just kind of dehumanizing pattern of events.

The same thing happened in Activision, if I recall. They had that bro culture in their executive leadership that eventually got outed, and people were let go. There was Google. I think Google got caught about 10 years ago just kind of...it was an internal memo that got leaked. And one of the executive leaders were disparaging the gender wage basis, kind of things like that. And they made some really insensitive comments in ink that got leaked in a memo that...it's just something that happens in the tech industry. And when it gets out, there's a zero-tolerance policy about how it is accepted in the industry. I think that's one good thing [laughs].

Like, if someone in our executive structure were to do something stupid like that and it got leaked out, they'd probably be on their ass in a couple of weeks. And it's just when to speak out. Sometimes in the tech industry, the industry will speak out for you [laughs]. You will not be accepted otherwise. There's a pattern within the tech industry of this kind of stuff of getting, how would you call it, a Darwinian approach to how you're going to be received [laughs].

WILL: I would say it's corporate size, like, entrepreneurs are a different breed of cat, they are. And they're not going to act right, but they started the company. So, you could kiss their grits, and it's good and bad. Madness and genius go hand in hand. And people with an entrepreneurial gene, or personality disorder, or whatever, they're out there, they just are. But you have to leave a substantial portion of who you are at work.

Like, you guys have never heard me tell you a dirty joke. And let me tell you right now, I love dirty jokes [laughter]. Like, I love them. I love them. You've never heard one out of my mouth. Even now, like, I'm not on the clock. I'm doing this one for free, but sorry, nope. Not going to do it. Sorry. Like, I might have gotten this podcast a PG-13 rating with my trash talk. But I'm actually not going to swear over the rest of the podcast because that was enough. That was enough. That PG-13, woo. Mm-mm. Not a word.

TIM: I don't know. I think you get the Silicon Valley or slopes around here. You get that attitude with a lot of these kind of startups. But I've met some really impressive people in the leadership realm who are...I think my favorite one that I've ever met was Scott Farquhar from Atlassian. At the time, he was the co-CEO of Atlassian. We had an opportunity, me and a couple of my peers, to have lunch with him. And I've never met a more straight-to-the-point, like, honest, no-BS kind of person.

He wasn't propped up. He wasn't inflated, wasn't anything like that. I was like, “I really like your stuff, like, what you guys are doing and how well you guys have developed. But you guys just don't support HIPAA certifications,” at the time. And I said, “What do you guys want to do about that?” And without even skipping a beat, his answer was, “Nope. We're not going to do that, at least not right now. I can tell you right now that's not on my roadmap, and I have no interest in doing it.” Complete respect.

I've never had a CEO executive reply in a straightforward manner. They're always diplomatic. They're always politicians with how they give you their answer, the majority of them, what I've got. But that guy, he and, I think, Mike Cannon, those guys, straight shooters, just some of the best guys I've ever seen. Really a good pleasure to be with those guys.

WILL: But that's a unicorn of a unicorn because I think that guy was the founder, right? Like, he was the dude, right? And so, entrepreneur. He got his business to, like, the ramen profitability, paying the bills. This is a thing. And then, he took it to a multi-billion-dollar level. And so, I mean, that's a unicorn of a unicorn. But even that guy there's a difference between the CEO that comes up through the ranks, and I was a director here, and now I'm the VP here. Now I'm a CTO here. Now I'm a CEO here. And you just sort of jump up, jump up, jump up. Like, this guy, it was his shop. And it is such a refreshing difference.

And it's why Founders-CEOs are still coveted to the degree they are. Because a professional manager who was appointed by the board and beholden to the board is just going to be like, “Well, we have a lot of quarterly initiatives, and we can get that on our roadmap. All our partners are valued,” and just some more word vomit.

So, your eyes glaze over and you wander off, whereas the founder is just like, this is my shop. Yeah, I can't do it strategically. It doesn't make sense for our company to take on this amount of infrastructure to support HIPAA, which I know a little bit about, and it's a tremendous amount. It's a tremendous lift, and he's just like, I can't afford it. And he'd just be like, no. But yeah, I don't know, man. There are a few entrepreneurs, and there are ducks [laughter].

MIKE: Let me observe something that's come from a number of these stories. You talk about complicity. Tim, you talked bro culture taking over sometimes. When that happens, there are people feeling uncomfortable. Obviously, there are people being mistreated, which is why it eventually surfaces and becomes a scandal is because there are bad things going on. But one person starts seeing it happen, and they don't say anything, and then they decide to join in. They follow the pattern, and then it grows. You end up with a bunch of people...you come in, and humans we absorb the norms around us, and we tend to follow them.

And some of us have an inherent punk rock attitude [laughs] and maybe naturally resist those norms. And some people are more prone to say, “Hey, I'm going to follow what's going on here.” In any case, there's a human tendency, and we can see this outside of...we can take this to extreme examples. Obviously, people cite fascism in Europe, you know, a hundred years ago, where a lot of people just kind of went along with it, even if they were uncomfortable.

There's this tendency where when a group's doing it, you don't say something. And it's interesting because even if you're reading the room [chuckles], maybe the room says, “We're all okay with this, and you're not.” And that's an uncomfortable situation to be in. So, what are the boundaries? It's not just about protecting your job, right? Because maybe it's worth leaving your job. When is the time when you say...well, so I'll take this further. If you were working for Enron and you didn't say anything, that probably is a black mark on your resume. There's times when there's clearly a line that's been crossed, and you should have said something. It was worth losing your job over. So, where do you find those boundaries?

WILL: Yeah, that's tough. I mean, I think, for most commerce, like, a good bright line is legality, right? I will not go to jail for any job. There's no paycheck. Like, I won't do it. There's not a chance. I have worked myself...personally, I've worked for defense contractors, many weapons of war, you know, in the hands of the United States military. We're killing people, and I have some sliver of accountability for that. So, is it morally gray? I have to say yes. I have to say that's a moral gray area because it's just the act of war, the act of violence, of taking human lives. But is it wrong? Ooh, no, I can't say that. Can I say it's right? Ooh, not purely. And everything exists somewhere in that continuum.

So, I'd say legality, like, that's a bright line. If you find yourself being asked to do something that is not legal for a job, for a paycheck, you should stop. And so, then it becomes a situation where if you disagree with something, I think you should argue, like, you should raise up your hand and say, “Hey, I don't think this is cool. I don't think this is okay. We shouldn't say anything.” And then, to the degree that you're empowered to act, I think you should act to do the right thing.

And then, when it's out of your hands, when it goes to your boss's boss, and then you're like, nope, this is this, then it becomes a situation where you have to ask yourself, do I stay, or do I go? And that's, I don't know, man. I have left jobs, and it was very, very difficult because...well, I'll tell this story.

So, I ran my own software company for 10 years. We made, a bunch of mobile app fitness products. I started it with a good friend of mine. We built it up. It was a seven-figure company. It is probably a seven-figure company. I had a significant equity stake in it. And we had some business relationships and some business arrangements such that I thought that the company was basically limited.

We had an artificial ceiling, where it was never going to be anything more than a job. And I had to ask myself, is this a job that I want? And the answer, to me, was, no, we should sell the thing, get a nest egg, get, like, a modest middle-class retirement out of it. That's what we would wind up with. We would wind up with a robust 401k. It was on the order of, like, [inaudible 34:55], think about it like that.

And me and my co-founder we had diverging of opinions. My co-founder saw it as this is the job I want. I'm the CEO. I can do anything I want. I'm the king of my little kingdom, right, and I love it. And I'm like, ah, but I'm not the king, not that it wasn't cool. I did a lot of cool things that you can't do in a big company. But we had this fundamental diverging of opinions. I had to leap. I had to go, and it did not go good. But that's sort of one of those forks in the road where it's like, okay, this is dumb.

There were other things that I mentioned where it's like, yo, we're making these technical strategic decisions that I think are really bad. I don't think they're going to work out, and they wound up not working out. But still, I'm just like, okay, well you're writing the checks, and that gives you the right to say, Yes, No, or Maybe. Like, I'm delegating that to you for the paycheck. So, you get to make the call, and I let you make the call. And then, this other thing where it's a strategic line of the road where it's like, I get this one life, and I'm not living it the way I want to. If we can't come to an agreement, I got to go, and that's that.

And so, how do you differentiate between, like, I don't think this is a good idea, but okay, which happens I think to most of us a lot. You can think about something you did today, where I'm just like, ah, I wouldn't have gone that way. How do you make that determination?

TIM: I see it happen all the time, but it never escalates to the Uber level of the bro culture. But I think every software development shop we always know there's a group of brogrammers that they act a certain way, and most of the time it’s just harmless. They're their own kind of way. But what happens is it just turns into a click, just like every other workplace. Whereas this time it happens to be software engineers, and they feel that they have the momentum and the numbers to act a certain way without consequence, and that turns into the bro culture.

And those always self-destruct over time because, eventually, one of those guys is going to do something stupid that HR is going to come down or the law and order of public...your PR is going to kill you when you do something that bad. But I think when you're in the engineering workplace, you just have to be self-aware enough to be able identify who the brogrammers are that may have a negative click approach or impact on their peers, fellow employees. And sometimes you just kind of have to steer clear of those people. Otherwise, you just add more fuel to the click, and then you're just, okay, great. We've got that going on, and yeah.

WILL: I don't know. I think the click-ish culture is, I think, I mean, I’ve run into some brogrammers here and there [laughter]. They’re really few though, to be perfectly honest with you. I’ve run into the bro boys. I’ve run into the bro boys in the sales team. I’ve run into the bro boys [inaudible 38:22]in marketing.

TIM: The sales engineers.

WILL: Less so MBA dudes, those guys can bro down. But devs, like, bro devs, pretty rare. It's just, like, the psychological skillset that you need to be an effective developer it doesn't sit well with the bro dogs. There's a lot of sitting still that you need to master if you want to do that job and brogrammers do not, as a general rule, excel at sitting quietly for many hours in a row.

MIKE: Well, I think that there may be some simple rules here. You said legality, easy. Don't break the law. There's another one, and this goes back to something we've talked about a lot: psychological safety, treating people with respect. If somebody's doing something that is dehumanizing another person, I think that can be a bright line. Like, no, I'm not okay with that. I'm going to say something, and that's my cue to leave.

I did leave a company a number of years ago because their marketing tactics were maybe legal, but certainly not ethical, taking advantage of people to the point where I just couldn't stomach it, so I left. When you join in that, by proxy, once you're dehumanizing, you've lost some of your humanity [chuckles]. And you've said, well, this kind of person is better than this kind of person. That kind of thinking doesn't have a good end. And I think that you can recognize that, look for that, and see that as a line.

I think there's a lot of things though that we haven't talked much about. It's just a technical decision, and we're going to have a disagreement. And, in most of those cases, you don't have to win [laughs]. You’ve been saying, Will, I will raise my opinion. I will share it. I will emphatically argue for it, and then I will agree with the group and [laughs] go with the decision that's made. A lot of times it's more important to have a decision than the right one, than the optimum one. Better to be going...you talked about rowing in the same direction.

If you're generally going in the direction that will get you where you need to go, you'll eventually get there, and it's a whole lot better than going in circles. So, I think there's a lot to be said for put in your paddle and just rowing. After you have clearly and effectively shared your guidance as to which way you think we should go, you get down and you just follow the leader.

WILL: Yeah. I mean, that's it. The only way it works is if you trust me to do my job and I trust you to do yours, and that's it. Like, as long as you understand where I'm coming from and why I wanted to do it, and, hopefully, I understand where you're coming from and why you're choosing this other thing, then that's what we got to do. And in terms of like, yeah, you can't work at an abusive or dehumanizing place. You can't do it for long. If you are in one of those places, you've got to get out.

I was not in this meeting, but a meeting was reported to me very recently at the big corporation that I’m consulting for that one of the VPs went in an AMA, and he said, “There's not a single individual contributor in this org that is operating at a staff level.” So, this is, like, hundreds of engineers, including many staff engineers on a level. And he's like, there's not a single one of you that's at that level right now. And I'm just like, woo, that's spicy, man. That's bold. Sure that's not you? [laughter] It was tough. It was a tough meeting. I was just like, wow.

MIKE: It's interesting you've said maybe it's you [chuckles]. If you're leading an organization and everybody is underperforming, it's usually something systemic. And you can blame people, or you can do something about it [laughs], and that's on you, I think.

WILL: If you gave me a hundred chances to either develop, recruit, or retain, like, a staff-level engineer, I could get one. I could give one of them, man, come on [chuckles]. That's just me. It is the little, old me [chuckles].

MIKE: That goes to the creating a culture of respect, that it’s just absolutely vital to have healthy dialogue.

TIM: There was one thing you brought up, Mike, the process of every time...so I had the experience. We had a new mobile app up and running. It was doing well. It was a primary mechanism during COVID for patients to get their COVID-19 testing everything. It blew up bigger than we thought. After we kind of hit a peak run time, the principal engineer brought up the idea that they wanted to move all the microservices into one monorepo. And the logic behind it, which was baffling to me...because I was on the DevOps and the CloudOps side of it at the time. The logic behind it was because Google that's how they do it. And this individual pointed out multiple big people out there who do everything they do in a monorepo.

But from a DevOps perspective, we had built custom pipelines in this whole ship-it mechanism that was fine-tuned, and we were easily bootstrapping a new microservice, getting it up and running, delivering a feature, all within a sprint, which is mind-blowing. The system is working. And then, they're like, oh, let's flip it to a monorepo because we don't want to have to keep doing patches on each repo on...And I was like, okay, just use Dependabot. Do something to help automate this thing. And it got to the point where engineers were getting very colored and very open about their feelings one way or the other.

And I don't think there's any argument in the world that will swing one way or the other that a monorepo or a microservice model is the right way to go when they're so religious about, you know, they have these stakes in the ground. If you've done this for a while, you just need to learn to step back and know your role as either a contributor to the conversation...this is my opinion, and this is why I think we should do X, Y, and Z. But, at the end of the day, it's the decision maker who's going to make the call, and you've given them the best information that you can. The decision maker makes the call, and you run with it.

And some people got so bent out of shape that one guy decided to quit because it didn't go his way, and it wasn't because...I mean technical reasons one way or the other, but it was more of an emotional decision for him to get out of there. And it's like, I don't think that was the right hill to die on because every piece of software expires in 10 years. We always replace something with a new something after a certain amount of time. So, what's the point? Just do the job and then move forward and let the decision maker who's hired to do that do their job.

WILL: Well, I'd say...I agree with you and, yeah, totally agree with you. But I would say this, if there is a series of technical decisions, strategic decisions at the management level where they're making these broad strategic decisions that just make your job suck, it just sucks to go into work over and over and over because it's just, like, this sucks, then you should find a new job. You should find someplace where you will thrive, and you will feel comfortable. And sometimes it's just a reset, where you just need different tech debt [laughter].

TIM: Yeah, that’s true.

WILL: [inaudible 47:27] Because we've all got our stink. But at the same time, you shouldn't do it in a huff. You should do it because, like, you made this decision, and I said, “Don't do it,” but you did it anyway. And now I'm stuck in this living nightmare every day. And that's a great reason to quit a job.

JUSTIN: So, I know we're towards the end of the podcast. But I did want to kind of get you guys’ feel for, you know, all of us are kind of more senior, right?

WILL: Allegedly.

JUSTIN: Allegedly. What are some good strategies to encourage discussions like that? Because, oftentimes, we could get to the point where we think we know what the idea is and everything and where we want to go. And we're trying to steer the direction of the discussion and go for the decision-making process that we think is correct, but oftentimes, we need other people's input. We need to encourage the next generation of engineers to speak up. So, what can we do? What are the strategies there?

WILL: I was in the debate team when I was in high school, and when we would do our little practices, everybody was expected to be able to take either side of the argument. And I think in an engineering discussion, it's almost never black and white. There are going to be pretty clearly good and pretty clearly bad decisions, but it's almost always a trade-off between two differing sets of ideals.

And I think in every good-faith engineering discussion, you should be able to articulate both sides. This is why I think your idea makes sense. This is why I think my idea makes sense. These are the fundamental values that we are fusing between for this and this. If we go this way, we get this. If we go that way, we get that. What is it that we value? And if we value set A or set B, then that dictates our strategic direction. But I think everybody should be able to do that in a good-faith discussion.

TIM: I had an awesome SVP once, and the way he did it when it came to these big decisions that had implications about framework changes, or big wide impact, he said, “Okay, I'm going to set the discussion up with the DACI framework.” So, Driver, Approver, Contributor, and Informed. “Whoever wants to do this thing, that's the driver. I'm the SVP, so I'm going to approve one direction or the other. And then, I want subject matter experts to weigh in as a contributor.”

And his advice to everyone who was a contributor was, if you tell me all the pros about your idea and you can't tell me one con, then you're way too religious about your perspective, and I don't want your information. You need to be able to tell me the pros and the cons of your position and remain objective. Otherwise, you're not furthering the conversation and giving me valuable information. And just setting that framework right up front really led to some productive decisions that maybe they were wrong, that's fine. But we were able to get through that process so fast and realize we were wrong quicker than debating it for four months and then finally getting there.

JUSTIN: I like that. I’ve kind of heard about that sort of thing before, but you put it together really well. Like, you have certain roles, and you expect people to play those roles, and encouraging people to play those roles makes sure that you get that variety of opinion, and it encourages people to fulfill that role. If you have a junior engineer, it would be like, “Hey, guess what? You are going to be doing this role here. I want you to prep for this meeting, and this is what we're going to be talking about.”

TIM: Yeah, 100%.

MIKE: I really like that, too. Come prepared to take the stance against your position.

JUSTIN: [laughs]

MIKE: And I'll often do that for myself in a meeting because I don't feel good about a decision that's not had any negative feedback. It may still be the right decision, but a lot of times you know it's the right decision because you hear the arguments against it, and they're all bad [laughter]. You have to hear both sides and sometimes that actually...in fact, oftentimes, that makes it really clear what the right decision is because you start arguing against it and being like, yeah, you're not making a very good argument, you know, it helps. And sometimes you dig and you find something that genuinely is a good argument and you realize, hey, well, maybe I wasn't coming in with the right idea.

WILL: I just default to constructive laziness. Like, what's the least amount of effort that I could do to get my job done over the long term, over broad, like, whatever my planning horizon is, which is not sprint level but quarter, if not year. And whatever's going to win me the quarter with the least amount of heartbreak and stomach acid, I'm doing that. Past a year planning becomes real hopes and dreams and moonbeams [laughter]. But you can plan a year. Like, a big organization can plan a year. [inaudible 53:23] plan two years. Don't [inaudible 53:25] your fairy tales [inaudible 53:26] [laughter]. Tell that to the investors. Save it for the board meeting, dude.

MIKE: I think we've covered some good material here. We've talked some about how to deal with just straight-up inappropriate things that shouldn't be said. It's okay. Speak up. Shut it down [laughs], and it's worth it. We've talked about a lot of these areas where it's not so clear and that we should say something politely [laughs] but emphatically.

There's a recent idea that maybe take a counterpoint so that you're clearly looking at both sides of the issue. And just the importance of not dying on every hill, of getting with the program, that a large organization or an organization of any size is only going to go somewhere if you're all going in the same direction, and push it forward even if it's not quite the way you want to go. And as long as it's not making you hate your life and your job, it's probably okay. You can live with it.

WILL: Yeah. If you hate your job, you should go. Nobody should spend all day, every day at a job they hate. You should go. If you hate your job because you didn't get your way, that is a deeper concern. I think you should probably introspect.

TIM: And you're still going to get paid. So...cool [laughter].

WILL: Yeah. Yeah. I mean, many times I have returned to my fundamental axiom, which is that I get paid either way.

MIKE: This is some good stuff because this is hard. Going back to the beginning of the call, I was in a situation. I didn't know what to do. I was young [laughs]. I was young and foolish. And I wish that I had today's experience then but you don't.

Hopefully, you've learned some things. When you're in your situation where you don't want to be regretting it 30 years later, thinking about what you could have said. Thank you everybody for sharing. I think we're in a good spot.

Until next time on the Acima Development Podcast.