The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack)
Episode 119

The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack)

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’.

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Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership.

In today’s episode, we discuss:


Where to find Michael Lopp:

Where to find Brett Berson:

Where to find First Round Capital:


(00:00) Introduction

(02:20) Beginning career at Borland

(05:41) The difficulty with shipping software at scale

(07:52) Why it’s harder to ship today than ever before

(09:42) What makes a startup operationally sound

(11:23) Why engineers should have concrete time to invent

(19:42) How PMs can improve engineering culture

(21:35) An engineer’s perspective on good product management

(23:36) The role of product compared to design and engineering

(26:38) How micromanagement kills creativity

(29:35) Fostering a debate culture in an org

(31:26) Declarative versus prescriptive leadership

(36:09) 3 ideas on leadership from Lopp’s upcoming book

(38:29) Understanding employee motivation

(42:28) Advice on discovering what motivates people

(46:06) Why teams should reorg every 6 months

(48:32) One thing all successful leaders do

(52:22) Why sound judgment is crucial for decision-making

(53:45) Crystallized lessons from working at software giants

(56:19) Why Lopp is afraid of becoming irrelevant

(57:58) The number one leadership lesson from Lopp’s career

(59:32) What Lopp has changed his mind on over time

(61:12) People who had an outsized impact on Lopp

Brett: Maybe kind of an interesting place to start and not to date you, but I think you began your career at Borland software and, I feel like for a lot of founders and product builders and engineers today, they may have not really heard of or don't know that much about Borland, but I feel like it was one of those consequential companies at the time. And I'm just curious, like what, what was the story behind Borland and, and what did you take from that place to kind of be one of the first places you started your career? 

Lopp: So Borland was my first place. I was out of college. I, was started in, in engineering there and Borland started under a guy named Philippe Kahn, who is kind of your pretty typical founder, in my opinion, in that he's like super smart. love to do everything.

Super passionate guy, sometimes a jerk, right? but really started, um, collecting this group of Europeans and doing software, sorry, languages. Pascal was sort of their first one, and then he expanded that over in Scotts Valley here in Northern California to be, Really a Microsoft competitor at the time.

It was all of the languages, led the charge on the languages. I would argue vastly influenced, uh, Microsoft programming language strategy. Um, but we expanded that to sort of be, uh, what turned into an office suite, which was Paradox, which is what I worked on and, uh, Quattro Pro the spreadsheet. So anyway, that was, to me, uh, this is many, many years ago. Uh, that was sort of one of the original, like, this is before Netscape, by the way. This is, you know, this is before the Netscape pop.

So this, but it was to me, one of those original sort of rapid growth startup things. We had this and still they have this most amazing campus. If you ever drive through Scotts Valley, there's, it's right there on your left. It says like this amazing building that, you know, everyone calls Versailles now, but like it's, it was, it was because Borland was doing so amazingly well.

And I learned how to be, I learned a lot of the formal. A lot of the things I believe now about engineering being like just a critical part of the equation because that's, we ran the show there that's, that's, and that's, you look at my history. I tend to go to places where engineering has an outside vote in terms of what's going on.

And that's because of Borland. This sounds super douchebag, by the way, but like every engineer had an office with a door because people what needed to close the door and focus. And I love, we talked about this before, I love jamming with people and bumping into people and serendipity, but I have stuff to do and I need to close the door and I, and that company recognized that of like, no, this is one of our more valuable assets and we need the, uh, we need them to be able to close the door and focus on actually getting stuff done. So all these little things from Borland sort of made me what I am. And then, you know, it became sort of mainstream with Netscape and all the other things that happened after that.

Brett: And it was like an early talent collector, right? it had this way of sucking up a bunch of really interesting people. 

Lopp: Symantec was out there at the time being that company, Borland, um, there's other ones. I think Intuit was kind of hot at that point too. Those are sort of the ones that I remember from back then. Borland gone now. I mean, it's sort of a husk for what it was, but some of those other ones were there, but yeah, it was that talent collector and it was that, there was that buzz about it to like, Ooh, if you're an engineer, you should be at the blow.

And that's, you look at my resume, that's what I'm doing. I'm going where the engineers are going and they're excited to go. 

Why do you think, back then and even today, it's not that easy to build and ship high quality software at scale? Like, obviously, it was earlier days back then, but here we are decades later, and it's still not particularly easy.

Well, I mean, it's one thing, which we already talked about, which is, can you gather the talent? I'm writing this piece right now for a future book about like, you know, Like this sounds insane, but I think there's literally founders who think, "Cool, but it's going to kind of contract out the engineering or kind of bring in some, some kind of, you know, an upside firm to do this."

This is a hugely horrible, bad idea. If you're trying to build software as to not, and I'm super biased, obviously engineering leader type here, but like there's people who think that. And there's people who think like "Hey, cool. We got to do consumer software, but I have a good eye. We don't need a designer.

I have a good eye." It's like, no, no, you don't. You literally were not trained in this. So like, you know, that's the design piece being, under invested and then you got the other side, which is like "Cool, I got an engineer. He's amazing. And I got a designer and he's amazing. We don't really need product people.

Like who are these folks? We know what we should do here." That's also a disaster. So like, I'm just picking one of the many sort of. initial conditions that like lead to a successful product and just even getting that triumvirate of product engineering and design is like hard. And we haven't even talked about this, the product market fit and the operations and all the things you have to build that you don't think you have to build and just pure straight up luck that you happen to be like at the right time at the right place, which I don't necessarily believe in.

I mean, I think it certainly helps, but like all the other things are helping actually show up and have everyone tell you, "Well, you were so lucky." It's like, yeah, Stuart Butterfield is a lucky guy. Right. Super lucky, lucky, like three times. Hmm. That's interesting. Um, you know, so it's just, it's all of these sets of things and, and just also in the face of so many people telling you, you can't do it because it's so incredibly hard one out of 10 makes it all this sort of stuff.

So you've got this constant chorus of humans going like, " Well, it's probably not 90 percent of these are going to fail so that's likely what's going to happen with you." You got to like ignore all that too on top of everything else. It's just it's a million things Sir that are this uh standing in your way

Brett: And do you think that that's gotten any easier in the last 30 years or no? 

Lopp: no I think it's getting harder 

Brett: actually. 

Why is that?

Lopp: Well number one is, because there's so many when, back in the Borland days, this is pre web, this is software that you print on a disk and ship to humans. So you've got, you know, you're shipping it once a year. So there's just this amazing set of infrastructure and tools and languages.

So time to market is super low. Like you and I could dream up something right now and I could chat GPT into existence in the next three hours, right? so that makes the time to market and how much can actually get out there. It's super noisy. You don't have this sort of elite set of not elite. You don't have this sort of set of folks that have been working so hard for the last three years. You got three months and someone's got, you know, you got 10 versions of the thing out there right now. So you've got this tremendous amount of crowded markets so how do you differentiate? How do you get buzz? How do you do all these things? So it, and that's, by the way, this is a great thing I'm talking about. It's sort of the democratization of product because so anyone can do it.

Anybody can do it right? And it's free, you know, to kind of build the thing and they're just out there. Those tools are there. That's awesome because it makes it available to anyone. But it's super tricky because you or I or whoever is doing that might have bad judgment and just start without a designer or start without really good engineers or not understanding scale or pick your thing. So this idea that anybody can do it means that anyone can do it well is not true. There's so many ways to screw it up. And it does come down to me, just to like, the coffee's kicking in now. To me, it just comes down to like good judgment and incredible operations. Which is sort of related. The ability to like, Hey, I have a million decisions.

This way, that way, this way, this way. Am I demonstrating good judgment? And am I operationally sound? Those are the things I, I look at when I'm kind of like sniffing out a startup. I'm like, who's making the decisions and how are they doing with those decisions?

Brett: What does operationally sound mean in your mind?

Lopp: Um, operationally sound. You apply at my startup. And, uh, this is 50 people, 100 people. Do you get a quick response from somebody? Do you, uh, talk to someone who knows what they're doing? uh, does the interview process happen quickly?

Are you getting a clue about who you're going to talk to? when you actually show up for the interview, how does that go? Like, is there a conference room? Do, do the people know what they're, is it just YOLO conversation? Or is there someone who's clearly thinking about this? Everything I'm describing to you is someone creating an operation to do hiring. And I've been through lots of interviews where they didn't respond or it was clearly just sort of ad hoc interview process. And by the way, the excuse is, "It's a startup, we're just making it up." Like, that's, you don't get to say that. You, you're building a product, but actually what you're building is a company, and that's an operation, whether that's the recruiting or the sales or the product process or the quality process or whatever it is.

And you're building it to scale. So if you're just shooting from the hip the entire time, you're going to get what you expect out of that. So operationally sound is, to me is, are the people who are building this thing, building it to scale? Are the operations predictable? Are they understood? Or is it just like three smart people shooting from their hip, making it sounding like they know what they're talking about.

And by the way, there's people that are really good at what I just described. "My God, you're so inspirational. This is great. Oh, you've got this all figured out." That's true. You need those folks. You need those Stuart Butterfields. You need those Dr. Carps and those sorts of folks. But you also need like that set of folks that are just like turning the crank, building the crank and turning the crank.

These are incredibly important. By the way, not sexy work. It's not sexy work at all. It's like process stuff, but this is how you actually scale the company is that operations piece

Brett: What is your engineering utopia look like? in, in an unconstrained fashion, you know, you can design the perfect engineering team where everything is perfect. 

Lopp: it's a good question. It's sort of a greenfield question, so I could go anywhere with this. But there's, there's, let's make me an engineer in this scenario. Because that's fun. Number one is, there's a very clear, like, 61 percent of, mmm, 71 percent of my time is very clear, I need to build these things.

And I know what I need to do. And I have the tools that are necessary to actually get that done. And I, and I'm getting it done and I'm getting positive feedback on getting that done. 71 percent. 29 percent this is Google time we're talking about, is like my own time to like do whatever the heck that is inspiring you based on the 71 percent of the time I'm doing it.

I'm, I'm, and it's, by the way, it's not useless time, but it's not necessarily time that I can explain to the product manager or the program manager. What am I doing with that time? Because, it's shower time, man. It's that like, huh, I'm doing this 71 percent task and it's good, and I like doing it because I like being productive.

But I can tell there's this better way to do it. Or, I can see this other feature that I'm inspired by it. Or, whatever it is. Um, I call it Wolf's Time. Um, which is sort of like, Sniff around and see what you want to actually go do next and kind of explore. And I think that's so important. I I think a lot of, and there's folks that like, just oh that's what I want to do is be wolves all the time. These are problematic, lovely engineers, but I want to, I want them to know that that's okay. My utopia is that engineers have a good chunk of time to do what everyone promises us during week of code or these other like one week things we have on build something and demo this to the CEO.

These are great things, but that's an always thing. That you're all thing that were built into the business is that engineers have that ability to do that. And by the way, we do this anyway because we're just humans and we like to be efficient or imaginative or whatnot, so but it's tucked into like the weekend or, or the schedule that I missed because I spent Friday working on the cool thing and I'm not going to tell anybody, by the way. So. That's my utopia is that there is that thing that 71 percent that's the real business and real stuff That's really clear and we're debating it and we're making it better, but there's also this free time to be kind of a free electron or a wolf or something like that.

Brett: What's the goal of the 29 percent time?

Lopp: To not be able to answer that question at all. It's the first thing, the thing you're asking is the thing, whenever I say some question like this someone like you and me I'm the same way is like cool, tell me how to account for that.

And the answer is there is no accounting because the moment we do that, then the project managers show up and they say " Cool, have you done your wolf time? Great check. Let's do that. Thanks so much. Great I'm like, good job, everyone. Now we're operationally sound." it's the shower time.

It's that time for something to be created. And you can't, you can't let the middle management VP project program folks, like, into that world. They will know when something's happened in there and, there's, there's just a pure engineering mental health thing that I'm talking about here, but there's also like, Oh my God, Adam, Ryan and Julia, they figured this thing out and now they're talking to people and now it's actually something.

And we're like, Oh, cool. And that it's like, it's spun out of that, that little creative circle, that poetry jam. And it turned into this other thing. And that doesn't always happen and you can't force it, but it will because they know what they're doing in their 71 percent time. They know why it's what's important to business and they're jamming on this other adjacent thing that they're not really describing what it is but it's real and occasionally things just pop out of it.

So the goal what you can ask is that crazy ideas are coming out of that and things are appearing out of that. Again, it just happened. You don't have to create this time, it just happens because engineers like to do that. And designers and project people, they're like, Hey, cool, covert op What do you say?

Let's do this thing. Right? So why not make it real? Why not make it something which is really well defined or. Maybe the right thing is for it to always be covert so the operational people don't show up and kind of beat the joy out of it.

Brett: Do you try to explicitly sort of run your teams around this idea or or you like for it to kind of show up in the cracks and. 

Lopp: it's a really good question, because I really obviously believe in this a lot. I tried to operationalize this at Palantir, and it was a huge disaster for most of the reason I kind of disimplied. I gave it a title, I said, this is how you achieve this. And this is how we will measure this. And it suddenly became this game of a thing where everyone's like, well, cool, I want to get on the, let's just call it, I didn't call it this, let's go on the wolf team. Cause I want to be on the wolf team because that sounds cool.

Right. And like, obviously there's status associated with this because this, these people have like 30 percent of their 29 percent of their time to actually go and do other things, blah, blah, blah, blah, blah. And it just became this, argument about like, who could be there? How did we measure it?

Who was good enough for that? Who wasn't good enough for that? Blah, blah, blah, blah, and it, it just, it collapsed because of that. So what have I done since then? I don't try to operationalize it in this utopian thing that you're asking. I just go over to people, engineers, and I say, " I know who you are." Because these types of humans that like naturally do this, just do it by the way.

But I go up and say, "Hey, Bob, how you doing? I see this thing that you're doing and I just want, and I know you're like hiding down the inside and yada, yada. I just want you to know, I know who you are. I know what you're doing and I think this is a great idea. So you should keep on doing this." This is often at odds with conventional wisdom about how to sip software. I'm literally telling Bob take that week to do nothing that is measurable by anybody. And I do that. So it's just the recognition of the piece. And I'll, I'll tell you one other thing that I do that's sort of operational, but I just recognize these folks that do this. Not for this one person, but just to people to know that I, as a leader for this organization really do value this thing.

And they talk, they're like, "By the way, Lopp sai d this is cool. As long as I get my 71 percent stuff done, I can go do this thing, right?" And they're like, " really? What does that mean? Blah, blah, blah, blah." There's a, there's a fine line here of like making it like an official thing. Because if it becomes official, then we get into the Palantir problem where everyone's trying to like game it and blah, blah, blah, blah.

But the thing I will do beyond that, once that sort of core set of free electrons or wolves or whatever you want to call them, is I kind of say, "Hey, cool. Hey, like every Friday for an hour, If you guys want to chat about anything or show off an idea or just jam on something, we can do that too."

So, and that turns into. By the way, this meeting always happens. There's no agenda. People just bring stuff and we just sit there and we kind of go, "Hmm, cool. What is this? Huh? That's interesting. Do you mean this? That sort of thing." And it's just that sort of stew. I'm just, just stir in the soup and then eventually someone goes, "Oh, cool. Well, let's maybe show this to somebody? What do you, what do you think?" Right? It's very, very light touch, but it's just a slightly more formality than me kind of poking people in the hallway going like, "Hey, I know you're thinking about this thing. What are you going to do about it? Yeah. Are you working on it? I know you are. I saw." Right? So just a little bit of formality so it's this really light touch thing, but I can do things to encourage it, which it's, that's utopia to me. Engineers, it's kind of like kind of being, having free reign to do stuff, but 71 percent on the books, operationally sound, blah, blah, blah. 

Brett: How did you land on 29%?

Lopp: I made the numbers up for you, 

Brett: Why did they come into your brain?

Lopp: Well, I, you know, I even, I said, I said 61, I'm 71. I'm like, I think a quarter of, and it's remember the Google one day a week thing is, so that's 20. So, I think there's just something, there's some comfortable number there, I think a day a week on this, but I even don't like that.

I think even the Google thing got gamed. No one's uses it now. I mean, I'm basically saying that, but like, I just, I think it needs to be real. It needs to be not measured any official way, but it's more than just, just like an hour here and there. I kinda, my dream would be that someone kind of goes like, "You know, Monday is pretty quiet post pandemic because I was still ramping and doing things.

So like I'm, you know, Monday when coffee's great from noon, from like 8am till noon, I'm off the books working on my other thing." And I want people to know that's great. I'm making it up right now I don't know if that's the right way to think about it, but if they don't know that that time is okay, then they're just sprinkling and they're doing it like when they're walking between things and as opposed to really closing the door and focusing.

Brett: if it's a bit antithetical to sort of talk about goals for that idea, is it easier to explain what a company or engineering team misses out on when that's not a part of the fabric of the culture of the engineering team?

Lopp: I don't know if this is what you're asking, but it feels sort of like a pivot, but like I have an issue with product managers and some of my best friends are product managers, by the way. So because, um, 

Brett: They're great people. 

Lopp: they're great people, um, like some of my favorite people for real. but the bad ones

think that, the bad ones create a scenario where engineering doesn't feel like they have a vote in what gets built. And the, this 29 percent time that we're talking about here is one of my countermeasures to that. In that an engineering culture where they don't feel they can invent things is a super bad engineering culture.

Engineering culture where someone's taking, you know, whatever so and so product manager wrote in Quip and says, "This is what we're doing and it's the law." Is super bad news bears to me. One of the things I do at my startups, especially when there's product managers running around doing their thing, I say "Hey, Julia, why are we doing this feature?"

And she says, and she would never say this. If they ever say, "Well, product said we have to do this" I get livid. And it's not that product is saying bad things. It's not that it's not a bad, it's that it's a bad idea. It's that this engineer doesn't understand why this is important. They've given up on understanding the importance of the why,

and they're like on the how, cause that's kind of what we do, we're how people, not the why people. You got to have engineering care about the why, because they're building it. They're literally building it with their hands. They, and maybe it's distance and far away and it's some e-commerce uh, uh, advertising metric that is far away.

I don't care. You still have to explain to engineering how it all fits together and why it's important because you want us caring about why. 

Brett: how do you define excellent product management?

Lopp: I'm literally writing this piece right now, which is arguing for the lack of them. So I'm going to get 

myself in so much trouble.

Um, I, we're not, we're not, we said we weren't going to talk about Apple, but. I, I think there's great product managers, but I think it's when they're equal parts and we're talking consumer software, if you're building like security software for the government, you know, boy, do you need product managers because they're domain experts. They're the ones who can explain all of the things there. But if we're talking about, and this is generally what I do, consumery software, which means you're building a software for regular humans, I would argue you have equal parts engineering design and product. Product is there to tell the story of the customer and to influence like to think like the customer, to think simply like the customer and not be encumbered by the how or the design.

So, that's what they do really, really well, but they're not, they're not, it's equal partnership between the three legs of the stool. Product, design, and engineering. The question I always get asked when I said this is like "Well, who, what if you have what if you have someone who can't agree?" Well, you probably got a CEO and he or she is responsible for, you know, voting at that point.

But I don't like that. I don't want them to ever have to do that. I want that team to be able to argue with themselves and say, " No, you're wrong. This is a design problem. This isn't a product problem. This is an understanding how the feature works thing. So design, you should listen to me and I get to decide here."

I'm making this up, or flip it around "No, you're wrong. This is never going to scale. Millions of people an hour are going to use this and your, what you're, you're suggesting product or design literally won't work because of this engineering reality." So. And we're going to have that debate and it's swirling around and sometimes designs right or gets the vote or sometimes products right gets the vote or sometimes engineering's right, but we're all equal participants and understanding the why and influencing the why because we all care about it because we're not sitting and going like, "Okay, that's right,

I'm not a designer, you know better than me, not a product person, you know, better than me. It's all equal, and that's super hard because of people and politics and dynamics and org structures and whatnot.

Brett: can you expand on the role of, of product? By maybe by talking about like, so what are the activities or what is that human or group of humans doing? 

I think it's more clear sort of what design is doing and engineering is doing a, again, in, in your definition, all organized around the why.

But I'm curious more about the product piece. 

Lopp: I just want to point out it's really interesting that you can't clearly, you and I both can't easily define it. So like, even the question Like, you just said it. "I know what design does. I know what engineering does. What is product doing again?" Isn't that a yellow flag?

Relative to sort of like How we build software, but let's give him, let's give him a shot in the arm. here's what they do, the good ones. They have a very complete picture, not just of the feature that we're talking about right now, but of the entire thing. I'll give an example, let's make it really simple. Why doesn't Slack have the ability to block people? They didn't until about a six months to a year ago.

What's going on there? It's like literally the first question I got when I showed up there as VP of engineering. I'm like, Hey, by the way, this person's annoying me. And we're like, Stuart didn't say it like this. He's just, he said, Number one, my vision for this is that all the information is visible to everyone.

So as much as we can, we're going to use public channels and everyone is contributing to this thing so we can see it. And it's like the knowledge base of like the organism. Number two, what did Stuart do before Slack? He had a thing called Flickr and I don't remember the specifics of it, but the moment that you turn in blocking, it turns into this whole political game because I block you,

and you get super mad at me for reasons and suddenly there's this whole other toxic thing going on about blocking and who did this and what did they say and it created this huge political situation inside of this community that suddenly you had to be worrying about that as opposed to why the community exists or the product I mean the business exists in the first place.

So that's why he's like, "Nope, not going to do it." And they did do it. They did it after he left. They added this feature to the, to the enterprise tier, or maybe it's all of it. I don't know. but what, why am I blithering and blathering about this? It's because he knew the entire system in his head and what he wanted Slack to be, which is small business to medium sized business.

People contributing the single source of knowledge, keep the politics and the toxicity low. That is a good product person that they can see this one feature in the context of the vision for the entire product. And that's why it's great when it's the CEO going back to Philippe at the beginning. He this Borland did office before there was office, man, that's what they were doing.

They define that. They got to ask, they got, they got their problems with Microsoft, but that's these, what these product people do is they really these are visionaries and they see these things and they can and we're talking about CEOs but I think there's non CEO versions of this, these people who can really put this feature or put this idea in the context of the the product that we're building, they don't obsess about this one little thing, they can they can tell you why this one matters relative to that one. That's the that's the vision piece and that's what a good product person says But I want to put an asterisk on everything I just said. There's no reason that design can't do this and engineering can't do this. In fact, we should. And if we, if we defer that responsibility to product, we're deferring an important part of our job as builders.

Brett: is micromanagement sort of antithetical to a bunch of these ideas? You've worked or been involved in companies that maybe have rightly or wrongly been labeled as CEOs or other people in the company orienting in the sort of command and control. "I have a vision.

This is what we're doing. This is why we're doing it" kind of a way. And I'm curious how that overlaps with some of the things you were just sharing. 

Lopp: It's interesting that you think that about the companies that you're thinking of, because it's, that's definitely a piece there and let's just maybe vanillaize that statement to be, they're strong visionary types like this is what I'm doing. It's my way of the highway.

That is, that is correct. Interpretation from the outside looking in. On the inside. And yes, they're there. And yes, they are the decision makers for like that big thing that we're going to go do. And boy, howdy, do they have opinions about the things that we're building? We're bringing it in and we're betting with them.

But every leader that you just referred to, every single one, when I'm right, and they're wrong and I can convince them of that in whatever scenario, they understand that. They go "Yeah... Lopp, yeah... shut up. You're right. Stop. I got it. I got it." By the way, what I'm describing super hard because they are super smart and they're smarter than me, but I, as we're picking up on this conversation, deeply believe that I need to understand the why of what I'm doing and when I'm really wanted to explain that and get someone to come over to my vision of the thing that we're building, I know it's my job.

Whether that's engineering or design or whatever. It's my job to explain why I think this is different or why this is better or whatever this sort of thing is. And those, those micromanagers that you're talking about, they deeply respect that they, and they do adapt to that and they change. The annoying thing is they're often right. 

Brett: That's why they're in the first place. 

Lopp: And that's their job in the first place, but when they believe that they're they're, they have to be right. That's a huge problem. So, uh, but they, they're not always right. And all these leaders that I've worked with, they have, what's the right kind of way to say this?

They all should have been lawyers. They love to argue and they've had different, they're giving up and saying that I'm right. Bar is wildly different. Some of them are like, yep, you're good. After like two hours. Other ones are like, year two. they're like, "Okay, Lopp... Shut up... You're right."

That's a different version of it there so, that's sometimes more work, but they love to argue. And I think just to pivot your question a little bit. I go to places where that debate and that argument, regardless of who you are, whether you're the intern or the CEO, is encouraged. And people know that they can raise their hand and say "Uh, Lopp's wrong.

This will never scale. Da da da." And I'm like, "what do you mean? Da da da." Like, like that, that is, that is part of the culture of these companies that you're talking about is that there is that. That debate culture that the CEO, she, or he has created. Cause they have a vision. They wanted to do things, but they also want, they're they're brightest and they're, they're talented folks to be arguing with them.

Brett: Assuming you want to create this environment of vigorous debate, are there intentional ways to do that, or is it more a byproduct of just the way that, in this case, the CEO behaves? 

Lopp: I think it's mostly the latter. I think he or she and his or her nature is a huge part of this. But I also think that it's not just their thing, it's also that founding circle of like those first five to ten. Because I think a lot of culture is the stories that everyone tells about things that happened a while ago.

A lot of culture that I, I've, I've shown up as like employee 110 or so, so a lot has happened, right? It's not, it's like they're, it's a business and I'm there to like scale the hell out of the thing. But I'm always listening for those stories because those stories about what happened early on, which are now kind of myths, even though it's been like three years, they're like saying "By the way, do you remember that time?

so and so and so and so, we're super drunk at the bar. And they were arguing about this thing and she was brand new and he was like one of the founders and they argued for a while and she said something important and intelligent, amazing, and that changed the course of the company. This brand new person had started a week ago."

I'm making this up. This is not a real story, but what happened there was a story got told, whether it's true or not, probably it's kind of true about our founders listened to everybody and they valued debate. And now that story is wandering around the system for reasons that are who knows why. The stories that are being told about the founders and the stories that are shaping the culture about debate or micromanagement or dictators or whatever it is. And it's, it's very, it's set very early on. It's not written down. It's completely detectable by talking to other people. People try to write it down and they say, Hey, your values and sort of thing, but that's not what it is.

It's like, it's the early ways that their founders and the company, treated each other. 

Brett: On sort of this thread of storytelling, does it express itself in the way that you lead engineering organizations? And, and you talked just a little bit about it, but as 

following as someone who's followed a lot of your writing and thinking over the years, it is, I find it interesting that it's also a cornerstone of the way that you communicate, at least written, you tend to have little stories and anecdotes, oftentimes anonymized scenarios, as opposed to just sort of saying, you should consider doing this or that,

it's often told through these little anecdotes, 

but I'm curious to hear more about it.

Lopp: Uh, well I have two contradictory answers to your question. Number one is you're you're 100% correct, which is, you, I, I, you probably even saw me bristle when you asked me about micromanagement 'cause that. Micromanagement pisses me off as an engineer and it has it's a probably need therapy but like I don't like to be told what to do Makes me mad My baggage not yours, right?

But I think there's a lot I think lots of builders are like that because we have this vision and we're doing this thing and blah blah blah. So Michael Lopp Rands, whatever his name is I don't want to tell you what to do because I don't want to be told what to do. But I do have all of these thoughts and stories and whatnot.

And if you go read my stuff, which you have, or you watch a talk, I am giving you a box and I'm filling it with interesting ideas. And then you get to go and put yourself, you in that box and see what you want to do with it. That's what I do as a leader. And by the way, this is, I have been criticized for this.

They're like, "Tell me what to do here." And I'm like, "Nope, 29%, not 71%. I want you to choose because you choosing is more important than me telling you. Because when you choose, you're putting yourself out there and it's not on me." That, that's like a fundamental like thing that I've always been is like, I'm the storyteller,

I'm like, get you thinking about this and whether I influenced you or not, I don't really care. I just want you to have as much information as possible. And I do care. I want you to make a good decision, but I want you to decide for yourself. Not because I said "You should have a one on one every week, no matter what." Which I have said that.

The contradiction that I'm going to say is I believe that I think actually a lot of people are right. And I think that I should be actually a little more, declarative in terms of the things that you should do, you as a leader should actually go and do. And the, I'm writing. I'm writing a book right now and it's the fourth book and I'm open with this, this thesis of like, Hey, by the way, I've been doing this for a while and I'm telling you stories and kind of giving you this soup that you can kind of consider and you can add to it or you can eat it or you can do whatever you want with it.

I don't care. this book, which is actually for very senior leaders is like. "Do this." "Every week, you should do this." And by the way, it is so hard for me to even like say that to you because that's not how I think and not how I want to learn as I it makes me mad. But I suspect that this will be very useful.

By the way, I'm saying it's for senior leaders. It's actually for any leader. And I think it'd be very useful to say, like, "Cool, well, he says are the 10 things I must do, so I'm going to do it". Which is going to get them to do it. And by the way, they're going to do it in their own way, right? They're still going to apply themselves to it, but I'm trying dictatorial oh my God, this is so hard to say. I think a lot of people want to be told what to do. Oh, I just threw up in my mouth and I don't, I bet these people don't even think that, but I think. I think it gets you started, right? It's not, you're actually not going to do it. I'm going to say, hey, go do this thing right now.

This is how you make coffee. You should do this right now. You're like, " Okay." And I wouldn't say it like that, but like, it's going to give you the beginning of motion. It's going to get you started. And the 10 things that I want to write about as a good leader that I think you must do are well earned and tested and they are correct and you won't only, you're only going to do four of the 10 of the ones, by the way, cause you're a human who has choice

but those four are literally going to make you a much better leader, as opposed to this story about this time between the CEO and this engineer arguing. You know, I'm trying to like abstractly tell you that, you know, debate matters, right? I think being a little more directive, maybe this is age, I'm getting older, but I think it's going to be more useful.

Brett: It's, It's, funny because I would think as, as you get older, you would shift In the inverse direction, 

where you move away 

from being prescriptive. It's like a Benjamin Button situation. 

Lopp: it's true. You're really right. I hadn't thought of that. It's, you're right. It is. And it's funny because I'm writing the intro to this book. I kind of say something like that, which is like, "The time you should have told me what to do was when I was on a brand new manager.

That's when I would really help because I'm just a blank slate, like one-on-ones, what's that?" Right? And I'm literally doing it late, later in my career, which I think is funny. And I think it's interesting. And by the way, I think it's, I, there's something, there's something clever about it, targeting it for senior leaders.

Cause you know, like brand new leaders are going to read it too. So he's going to go, "Oh, this is interesting. I should do this sort of thing." So we'll see.

Brett: can you share a couple of the types of ideas that are in the book that you're working on?

Lopp: The one-on-one piece, this is like, sorry, this is like standard Rands stuff, but like, that's still like my go to one just, and by the way, it's not just a one on one it's trust, which we just talked about. It's that like this person's looking out for me and we, communicate regularly on high bandwidth things.

So that's, that's an easy one there. I'm just going to regurgitate things we already talked about this debate culture. both my current employer and all the companies I love working at is the reason the product was good the debate culture is super hard. It's not fun. You walk in with your idea and smart people that are vastly smarter than you just tear it apart all the time.

And very often they're right, and sometimes they're wrong. And then when you're wrong, you have to detect that and defend yourself against it. This is such a, an important part of a team. And it comes to the trust piece that like, we're just, we just want this to be great. And I'm going to give you honest feedback about this ideal op that you brought in that is hot garbage. And we're going to talk about it and we're going to take the 2 percent that's good. I'm going to make it 50%, right? So debate culture is another part of that, of how do you create that in a way that is. Healthy, not toxic and is additive to the, to the product. So debate's another one.

Sorry, change management. It's the most boring topic ever, but taking an entity of people from point A to point B, without everything blowing up while you're doing that. It's super hard, especially during rapid growth. So how do we, how do we do that in a way that is respectful and low drama that's another one that's there.

That's a bunch of communication inside of that, how to communicate as a senior leader. That's another one, which is by the way. You say it, you say it again, and you say it another 15 times and I'm shaking my head because I don't like to do it, but it's actually how it works is you got to repeat yourself a lot.

I think the other one is, and I don't, this is not very crisp yet, but we kind of talked about a little bit is sort of the, the nature of the three parts of the business: product, engineering, and design, and being very deliberate about, and this ties in with everything that we just talked about, being very deliberate about who, who's the expert, did, are you choosing to build that function?

Great. what power do they have? Great. Um, how does that power relate to the other two, seats? Good. Who's the decider when there's an impasse? Okay. Right? All of that is just really basic stuff when I say it like it, but I always try to like encourage it via poetry as opposed to practical, like, you know, dictatorial dictates.

Brett: Living in sort of this um, storytelling leadership style, when you're trying to give people a suit for them to figure out what to do, are you doing that with an end in mind for them, or you are doing that and, you know, "Here's everything and you may make a souffle or a soup or what..." you know. 

Lopp: This goes back to the book too, I think for every single person who works for you, whether you're a brand new leader or you're a VP, you should know exactly how you need to grow your team. And if that's too big of a thing you don't know yet, you should at least know what motivates them. I had an admin at, uh, Palantir she was amazing.

Um, and this was one of those, like, you saw someone who was amazing and you're like, "Oh my God, I need to work with this person." and She wasn't an admin at the time, but I'm like, "you would be an amazing admin." She was running my business there. Early on, she's like, "I just want you to know I am coin operated. You throw money at me, everything's going to be great." And it sounds kind of douchey and it sounds kind of weird, but it cleared up everything because when it came to bonus time or whatever. I'm like, "Okay, cool. Carrie just coin operated. So I'm just going to dial this up and make sure she sees that I did that."

And she was, and we were great. And that's a simple one and Carrie had other things that she wanted to do and a bigger career, but she was just really like, she's like "Money is what I want" you know? it's a simple one. It's an, that's an easy one to do, but for everyone that works with me right now and anyone I can think of, I can say, " This is their primary motivation" whether that's, they're very happy in their current role and they want to like focus on getting better at that or they desperately want my job or any other thing is I have to have that in my head.

You have to know what that thing is. this is why the one on ones and trust are so important because you learn it and you're just, your, your responsibility is to continually invest in that, then they can see that because that's, that's the trust thing again, is like you, you see that person is looking out for you and making sure that you're growing.

I am accountable for knowing that thing, but it's great when someone is as transparent and as motivated as Carrie to do that, but that is exceptional. That is not always the case. And sometimes, I need to kind of craft that thing with the person because they don't know. 

Brett: Yeah, so talk more about that. I'm incredibly interested because I find a vast majority of people don't have that level of clarity.

And so you kind of have to root around or co-create it. 

Lopp: And you also have to like not be yourself because I'm like, "I have a short attention span. You look at my resume, I'm jumping around every three years. So what do I want? I want constant stimulus. It must be interesting and new and always forward." This is Michael Lopp.

You now know everything you need to know about me. that's not me, but that's me. That's not making up a person, Bob, Bob. Like, I can't. Everything I just said about me, I got to like, let it go and know that these, everyone's a beautiful chaotic snowflake and I got to understand, root around with Bob what he wants.

Bob, hypothetical person, likes stability. Bob likes hard technical challenges. Bob likes to be feel like he's valued, whether that's compensation or recognition or whatever it is, but his core motivation is: I have to keep putting huge ginormous technical problems in front of him. And that's it. And all the other things have to happen as well.

But I learned that by talking with him and kind of going, okay, cool. Not a climber. Doesn't want to be the next level up. Doesn't want to be a manager. Just likes the sense of like solving hard technical challenges and being compensated and recognized and that sort of thing. But that's, I'm always looking for that core thing in people and here's a, here's a controversial one. There's times we spend a year. I'm like, "You don't need to be here anymore. You have learned everything that you're going to learn here at Slack. It's time to go somewhere else." And I wouldn't say it like that, but there's, truly a, a healthy part of the job is when you're like, "This role that you want Isn't here. It's over at Stripe or it's over at OpenAI or something like that and we're going to figure that out." And this is not a performance management situation. I'm not managing them out. I'm just like, "I don't think I can give you what you need here" and I can manufacture quite a bit of things, but that's truly your job is to make sure that there is to make sure you understand that thing and you're, you're growing in the right direction.

So, even maybe outside of the company, that could be the right thing.

Brett: For folks who don't understand this about yourself, what are you doing in the way that you're interacting to build this portrait? 

Lopp: It's one of my superpowers, it's just curiosity. Like I'm always like looking at something and going, "Hmm, why did she do that?" And I asked her like, "Oh, that is interesting, why did you do that?" And she's like, oh, I'm like, oh, okay. And then I do that another hundred times.

And every time that I'm kind of curious, I'm like, "Huh, that's strange." And then I'm, what I'm doing is I'm modeling, I'm pattern matching in my head and going like trying to find, Oh, cool. This is another Carrie or this is another Bob or the, and they're not truly that, but there are, you know, archetypes if you will.

So, but it's just that curiosity of trying to figure out what this particular hand of people I've been dealt and who they are. it's just curiosity. And then asking like, "Hey, you got super mad when X happened. was it this?" And they're like, "No, it wasn't this at all." I'm like, "Whoa."

And again, it's just me trying to error correct and figure out that whole thing. But like, I'm not really sleeping at night until in my head, my team of people and my extended team of people, I kind of know how they're, how they work. that's literally my job, right? I, like, if they're all gone, I have exactly no job.

My job is the people this, Understanding how they tick or getting them understand how they, getting them to understand themselves, how they tick is like a huge part of what I do.

Brett: When you think about these different archetypes or motivations or the way that people behave, do you think most of it begins in whatever happened, you know, under the age of 18 and it's all sort of one thread that ties it together or no? 

Lopp: I've had Joel Spolsky was who inspired me very early on. I'm not going to quote him here poorly. He really truly does believe what you just said, which is like that, what you did when you were a kid and how you were treated as a kid really is a lot of the baggage you're bringing into an adult, which, yeah, I kind of agree with that.

but it sort of infantilizes what is very important work. So let's just talk about me because it's easy. Like, why do I not like to be told what to do? I have never had therapy. I don't know. I had an older sister though, and I didn't like being boss drowned at all. Right. Sorry, Christina. I didn't like it at all.

It like super bugged me. I'm like, "I actually know what you're doing here. Stop telling me what to do." So is that it? Uh, maybe, I don't know, maybe I need more therapy there, but that's not the point. The point is, I know for me, this particular deficiency or trigger or thing that I have, and I'm aware of it. And if you like, if you started to tell me, like, "Hey, Lopp, I'd love, I need you to do this thing." Or, you say, "Do this thing for me." The moment I hear your tone of voice that is telling me what to do, I, in my head, I just cross my hands and I just take it because I know I'm going to get mad, which I'm going to, but you're never going to see that.

I know I have this way that I work or the way that I think and I've developed a practice that allows me to not convey something completely unfair to you, which is I'm mad cause you're telling me what to do. You're doing your job and you're asking me to do something totally reasonable and I'm this weirdo.

it's more that I've learned how to manage it let's just turn it into a positive. I've written lots of books that are this poetry and this soup building thing because I want people to think for themselves. So there's a positive side to it as well, which is like, cool, I'm not, I'm not a dictatorial type. But I think it's, back to your question is figuring it out is those things that they, those core motivations, those core behaviors, that's like your job as a manager to understand those things and to get them to recognize it if they don't and also to give them tools. By the way, yeah, you interrupt people all the time. I don't know why. but let me tell you what happens when you interrupt someone, whoever that is, right? Let me, a consequence, and like, here's what I do when I get really excited about the thing that you're saying, and I'm going to interrupt the other person.

I think this and that, and then you get them to update their toolbox, give them another arrow for their quiver, whatever it is, and turn it into a thing they recognize and also a thing that is hopefully an asset or a, uh, a benefit for them.

When you 

Brett: think about these core motivations, or behaviors, do you think about them in the context of the team that you're creating? So, normally, I think people think about teams in terms of skill sets, but like these kind of core deep beliefs. "I want stability. I want change." I want do you is that a way that you construct teams or it just emerges after? 

Lopp: One of the downsides of rapid growth startup is you don't really get a lot of that during the interview process. So this is one of the reasons we reorg every six months is I, I truly believe we're learning those things and going like, Oh geez, Julia's amazing at this and Marcel is great at that.

So like, this is more of this and this is more of that. This is why that's there. Your question is, am I thinking about that? As soon as I know it, as soon as I can tell, which is not usually until a lot of time has passed, I am starting to optimize for it. I'm starting to build a team around it.

And also, very importantly, if I have a person of model X, I know that Y, B, and C are great complements to that. So I'm going to go take that X. I'm going to put a B with it as well, because they need a little more poetry because they're kind of a dictator, but I know they'll get along with this B.

So I'm, I'm thinking about a lot of those things as I'm sort of constructing that, that is the majority of my job is what you're asking about. And by the way, it's not like I'm actively doing it every day, but I'm looking for how to optimize the team such that they have that whatever core set of skills for that technology or product that they're building.

And it's not just one person, it's the whole team.

Brett: Do you tend to not spend time on this before in the interview process before someone joins?

Lopp: I try to, but I think I'm lying to myself. it's not enough time and you don't, you got to see someone with bullets shooting over their heads to see who they truly are. it's, it's fine. Interviews are great. You learn quite a bit, but like, I've been trying for this forever that's kind of like root out, and I'm looking at all the feedback in the first round, and there's some yellow flags and I'm like, I'm literally going to construct a specific task with this person for round two so that I can learn about this thing.

it's still elementary. It's still like, it's still like the early times. It's just us talking about it as opposed to actually seeing the person in the trenches doing this stuff and in the trenches doing this stuff is when people do their best and worst work and they're also their most honest selves.

So, I think you can learn on interviews, but I, I think you're getting a facade. I think you can learn from background checks, but there are people that are, they're picking the people that they're telling you, you got to do like unsolicited ones are actually the ones that are actually interesting because someone who hates them tells you really interesting things, both positive and negative.

So yeah, interviews are good, but it's not, it's so much more to learn.

Brett: Where does this leave you in terms of the things that are most malleable and engineers or team members? Like, if some of these things, right? If somebody just has a tremendous desire for stability. My guess is, it's fairly unlikely in the course of working together, they're going to want instability, right?

That tends to be a little bit more fixed. Are there things that are quite malleable?

Lopp: I'm going to twist your question a little bit. the question is, do they want to be malleable? That's number one, like stability guy. No, I'm not going to change that. He's going to be, he's going to be at that company for forever. And that's what he's going to do. And my job is to optimize around that.

But then there's, let's pick on leaders because I think leaders have a higher bar in terms of interacting with other humans. So they have to have lots of faces and lots of masks and that sort of thing. So one of the early things I do with brand new managers is, do you truly respond to feedback and do you update how you work based on the feedback that I give you? Failure to do this as a new manager is a big red flag. Because you have to be other people. You have to meet other strange people on their terms. and speak how they speak. Because they're not going to speak how you speak. Because that's not who they are.

So you've got to have this job of adapting and not. being duplicitous, but like just being, you know, understanding all the different personalities out there, but you have to be willing to take the feedback, something that people, most people, when they hear feedback, they get really nervous and say, "Okay, I'm going to be fired, but tell me why."

That's not it. It's the, here's the thing that you have to really work on. And yes, you need to hear it and be scared that somehow you're failing because this is feedback and blah, blah, blah, get past all that. I get it totally. And then actually change and not like change who you are as a human, but add that new skill to your repertoire of like, huh, okay, I am bad at being told what to do. Here's the thing that I now do, right? Whatever that is, it's your choice to actually change, not change, but adapt. So that is there and managers really leadership types. that's a huge part of the gig. Cause it's not stability, Bob.

Stability Bob's great. He's doing so well and I gotta keep hard things in front of him and I know that he works well with these types of people. He doesn't work well with these types of people. I'll referee that. But then there's these other folks where they're high connectors. They're, they're scale functions.

They're like grow the business types. They, they have to be adaptable and learning and they don't get the benefit of being the CEO. And everyone is like "Okay, cool. She's the boss." There are all that other piece of, uh, people that are connecting all the things and they have to be able to learn and educate and always be moving, moving forward.

Brett: What are the other things in your definition when you're when you think about great leaders? What are the other things that they are responsible for?

Lopp: Wow. That's like a whole podcast right there. Um, um, 

Brett: Shrink it down. I think there is a declarative 

Lopp: communication that they're amazing at, they, they're like incredibly good communicators. They don't blither and blather. They're like, they can tell you the story and it inspires you. I think that's a super big part of a leader.

I think demonstrated sound judgment. I used to say good judgment, but I think sound is actually a better word, which is like, Hey, I'm going to do this thing I'm deciding. And here's why, and this is communication again, and this is my decision. What do you think? And you're like "Huh, I totally disagree, but you're the boss", or "That makes reasonable sense to me and I'm willing to follow you there." but that's, it's not the communication piece. That's a big part of it, it's the, it's the soundness, like, "Does this make sense?" There's another one, which is related to that, which is something I struggle with because I have a short attention span, which is reliability, which is, Can I expect what I get out of it when this leader says I'm going to do blah, do I have a high faith that he or she is actually in deliver on that thing because there's a lot of folks are Like really good in the all hands and they're pitching and they're waving their hands and they're like, "Oh my god I'm so inspired" and then nothing happens because they thought the idea was more interesting than the execution.

and also I think another part of a really good leader. We talked about this earlier, operationally sound, the machine is running well because they're aware of what the inputs and the outputs are and what good looks like.

Brett: you expand a little bit more on this shift in language from good judgment to sound judgment and why you think that is more correct?

Lopp: You're going to disagree and I need to convince you of why this decision that I've made is sound. I'm big on the word accountability. Accountability, if you ask most people what accountability means, they say, " Well, it means if I don't do what I said I was going to do, I'm going to be in trouble." It's not what accountability means at all. Accountability means to give account, to give the story of why we did this thing. Account. It's literally in the word accountable.

I can explain why we're doing this and I am accountable for it. I can tell you why. Sound judgment is judgment which is maybe you won't agree with it, but it is explainable, discernible, and you understand why I'm choosing to do what I do. And the reason good sounds bad is like good sounds like I'm selling you on it.

Like this is a good idea, right? No, I mean, yes, I can market things and whatnot, but I want it more to be like, Is this a sound idea? Does this stand up to scrutiny? when I explain the story of why we're doing this, do you believe me? And if you don't and you tell me and I convince you otherwise or I say this is the way it is, you go, okay, well it's sound enough that I'll do that.

There's something really interesting there in the, in the split between the two words. Good is sort of like, I'm trying to sell it and sound is like, do you believe it? 

Brett: You've worked across so many iconic companies and I'm curious, is it possible to crystallize some of the big ideas that you were only able to figure 

out? Because you've had this set of experiences at such wildly different, but all incredibly interesting and important companies.

Lopp: That's a really good question. I think we have to go back to Borland most of the companies I've been with are with some rare exceptions, oral exceptions. I'll get to your question in a second. I generally go to places that, this is too small of a word, have buzz.

Um, there's something about them that is intriguing the engineer denizens of the world. And by the way, just make a list. Borland Netscape Symantec, uh, that startup you've never heard of. Apple Palantir, Pinterest, Slack, Apple again. There was something about them that everyone was like, "What the hell is going on there?" And I'm making it sound really simple, but when people look at the last three companies I was at before they all share totally different government software Pinterest, you know beautiful idea catalog and then slack communicate totally different businesses.

They all had this buzz factor. The reason I'm harping on this one is because that buzz is both deserved, but it also gives me a very clear sign of when I arrived there, the kind of company I'm gonna be at. Which is engineering matters, rapid growth, smart people. Like, like, there's like, it's, it's, it's always, it's never been the reason I've gone there, but I've always have gone "Oh, yep, here it is. Here's the 14 that are like doing the thing." This is, this is, they're doing this. They're always there. And, Correlation, causation. I don't know. So that's why I've showed up there, but, and this is going to be unsatisfying part of the answer to your question, they're all different. They're all totally different sets of people. And Lopp, the learner, the curiosity guy, the pattern matcher, pattern matcher has developed quite a Catalog of all the different types of humans and all of their attributes, probably better than most because I tend to leave every three years and go find another set of humans to understand.

So I have that. That's the thing that I have now, which is sort of just years and years of these, all these different types of humans, these smart ones, these builders, these buzzy types, and kind of knowing what, how they tick in totally different contexts. Government software. Give me a break. That's the night and day from Pinterest.

That wasn't, but I can tell you the, who are the similar people between those two populations and how they're motivated. So it's that tapestry of just all these crazy, lovely humans that I've, I've got an opportunity to learn about.

Brett: Do you think there's something about the way that you behave or the way that you're wired that has allowed you to work in so many different environments? I find something that I've noticed is, depending on, on the person, their environments where they're tremendously successful and a vast majority of that same person, you plop them somewhere else, it wouldn't really work. But to your point, it's, there are some threads that are similar, but these are very different companies, different stages, different missions, you know, et cetera, et cetera. 

Lopp: I'm deeply afraid of becoming irrelevant. And it just, it can happen in two years. You can be at that place that's so totally not relevant anymore. So scared, afraid. These are words I am using with you right now.

And that means that I have high motivation, higher than most, to constantly learn about the next thing, which means I'm jumping between totally different high buzz companies because I want to understand. Cool, how are we really going to do advertising? Interesting. How are humans really going to communicate at scale in an enterprise?

Interesting. it's that fear of being irrelevant that's driving a lot of the constant sort of, analysis and enjoying new problems. But I also just like to learn too. This is the thing. I just, it's fascinating to me to like, when I see a puzzle, like, especially now after doing this for a long time, when someone asked me a great question or they behave in this way, I'm like, " I have no prior model for this."

Like, okay, this is the thing I'm going to obsess on for the next two hours. Um, that's fascinating to me is that, is that learning piece. I think that. And that's the other side of the fear is this, I really like to learn and as evidenced by my corpus of work, sharing that with others so they can, they can learn from it and, you know, perhaps poetic ways, but maybe less poetic ways in the next book, we'll see.

Brett: if I were to watch you as an engineering leader in these different roles, are you quite different or it's. It'd actually be quite similar?

Lopp: Well, it's interesting, it's a good question. Like Palantir, I kind of was hired as a leadership consultant before they made me a director. So I was kind of just bouncing around kind of being a therapist, and I say that with raising eyebrows, it was fine. And then I got like a role, that was totally different than my first VP gig at Pinterest.

side thing. You're not, you get a new role, you're not good at it for three years. And nobody wants to know that because like I got to be a director in the next two years, like, yeah, you're not even a manager yet. Good luck. So would you recognize me VP of Pinterest versus VP of Slack?

I was totally vastly more qualified VP at Slack than I was at Pinterest. And I don't know if you'd see that. I mean, if you're sitting there walking around with me, but I think you would have, if you could compare the two because being comfortable with abstract at a distance influence, there's communicating broadly and understanding 30 percent of the people always going to hate you. It doesn't matter what you say. You're always going to be pissing off like minimum 30%, like all the time. I tell this to leaders now and they're like, no, I'm going to be fine. Like, no, you're talking to 3000 people and you're saying this thing, you think you're going to address all 3000 people?

No, you're like, there's a chunk that's going to be super mad the job is that, you know, is that people are super angry with you a good chunk of all the time. It sounds horrible. It's just part of the gig. That's one of the lessons I learned from Pinterest to Slack.

And there's a bunch of other ones that shaped how I communicate and how I chose to invest my time and the teams that I built. So you'd still look like me, but I think you would have seen a pretty different leader. It's just using VP as a before and after sort of scenario.

As we wrap up the last couple of things. 

Brett: one,

you know, we landed on this kind of interesting area when you talked about the new book that you're working on. In some ways, you sort of shifted some perspective such that maybe there's more value in being more declarative or more prescriptive. Are there other things like that, have caused you to sort of change your mind about?

And I'm, I'm particularly intrigued because you've done so much writing and thinking on a lot of these ideas and now decades in, are there other things that have bubbled up for you? 

Lopp: One thing I flipped on, I used to be, I don't know, 10 years ago, be like, stop coding engineering leaders. You shouldn't do that. And I, that was 100 percent incorrect. I code all, I don't call it all the time, but I'm, practicing something in Swift right now

because of reasons. I'm not like checking in code at the place I work at, but, you must stay technical as a engineer. They can tell, they know when you're no longer doing that and your credibility, it's not gone, it's just different. that's one that I've changed a lot on. The pandemic was super hard for me because as people person, like,

staring at this postage stamp that is you right now, I'm getting like 40 percent of the signal. If we were sitting here in a conference room doing this. I could see what you're doing with your feet. I could see what you're looking at right now. I mean like blah, blah, blah. So I deeply appreciate the value of remote and I think it can completely work.

It's not my jam. I want to get together with the humans and go high bandwidth and debate the thing. So the pandemic taught me that, you know, I've always been sort of like, Everyone has to be here. I'm not that way anymore. There are things which are required that we have to be here together.

And I believe that even more, even in a world where there's a chunk that it can actually totally happen remote. But you're deluding yourself. You don't think humans aren't at hanging out together and getting stuff done. So, those are some things I swapped on. There's probably others as well.

Brett: Maybe to wrap up where we always do, and this may be particularly tricky for you, given your career. But is there a person or persons that had an outsized impact on the way that you think about all these topics that we explored? 

Lopp: It was the first engineering manager at Netscape, a guy named Tom Paquin. He was the first engineering manager. I was kind of new engineering manager in a different team at Netscape. And Netscape, once again, high buzz instantly found the relevant party and they were all hockey players and I was a hockey player playing hockey with all the founders for like two years. Um, and he was part of that crew. I left Netscape when, uh, just before they got bought by AOL and he actually came, this is, I really admired this guy, engineer from SGI.

And just super terribly smart. You know, these folks, you're like, "Oh God, you're so much smarter than me. I'm never going to be like this ever." And, and he was just, he was just willing to give his time. And I was at the startup as their first engineering leader. And he came over to consult for us. He was like our interim VP for like, I don't know, seven months or something like that.

He said something that changed my life. And this is the moment that there, it's the reason you and I are sitting here right now, by the way. He said, I was sitting in the ping pong room at Icarian, which is the name of the startup and he goes, "Hey, Lopp." I don't remember the reason we were having this conversation.

He's like, " You're a pretty good engineer." I'm like, "Oh, thanks." He's like, "You're never going to be great engineer. You're never going to be that guy and you're fine. Like you can do this sort of thing." And I'm like, and this is, he's a straight talker. Like this, this is not, it's like low comedy guy. He's just like straight talker type.

He's like, " The thing that you do is you understand how the humans work well together and you think that everybody knows how to do this and nobody does. So what I want you to do in your career is I want you to. Understand this is your superpower, this people thing in an engineering context, because you do that and you're going to be wildly successful."

He didn't say it exactly like that, but if you know my career and you know everything we just talked about, we didn't talk about technology. We didn't talk about scale. We talked about culture and people and communication. This is all Tom. And his total, and by the way, he's like, it was the compliment that got me.

He's like this thing that you think you're good at, you think everyone's good at, no one's good at it. And you'll be amazing because of that. I'm like, okay. I started the blog like two weeks later. that I was like, okay, cool. I'm just gonna start writing about this stuff. And by the way, I was just, 'cause there was no good books on it.

That's why the first book is dedicated to him. And uh, that was, that was one person recognizing one thing at the right moment in your career. That changed everything.


Brett: that what you now aspire to do for others?

Lopp: Yes, I do. This is why I think compliments are amazing. Number one is we're a pretty critical society by the way. But like people do something. There was this guy walking in front of me at the mothership and there was this piece of trash on the ground. I don't know this guy. And he stopped. It was like, pretty clean campus, by the way.

He stopped and he picked up the trash. Doesn't have to little piece of something, whatever. And I'm like, I'm like, "Thank you. You're awesome. I saw you do that." Right? I know who this guy is, still don't know who this guy is, but he stopped to pick up the trash on the ground. And I was like, I love that. I love the attention to detail.

It's an Apple thing. Right. did I change his life? No, probably not. Did I recognize a small act of kindness? Yeah. And do I know when the thing that I'm saying that's a compliment or an observation or feedback is actually going to do the thing we just talked about Tom and I? I don't know.

But I do it a lot because I, I, I see the value when someone you respect takes the time to actually go and actually give you the feedback or say something positive or say something critical. So. Yeah, I want, I do that because I, you never know when that thing is going to like transform people. That's why I write it too.

Because the writing can do that sometimes too.

Brett: Thanks for spending the 

time with us. This was fun. 

Lopp: that was great. Your questions were amazing.