The Puzzle of Engineering Leadership, with Michael Lopp

Ep 17

Oct 04, 2023 • 48 min
Michael Lopp, aka Rands, joins Allen to talk about the fundamental need for growth, finding your team’s core motivations, the value of writing for developing clear thinking, the joys and perils of writing a book, the art of a compelling presentation, habits for editing and refining writing, and fostering clarity of responsibility – and curiosity – on your team.

Allen: Welcome to It Shipped That Way where we talk to product leaders about the lessons they’ve learned, helping build great products and teams. I’m Allen Pike, and today’s interview is with Michael Lopp. Lopp has worked in engineering leadership at places like Netscape, Pinterest, Slack, is currently a senior director of engineering at Apple, is also a prolific writer, both with print titles like Managing Humans and online under the pen name Rands. Welcome, Lopp.

Michael: Glad to be here. Thank you for having me on this lovely day.

Allen: I am very excited to have you on here. There’s so many engineering, leadership and presentation and team building and just surviving as a tech person at technology questions.

Michael: Surviving. That’s a good line.

Allen: Well, I think it’s maybe a little bit… so I’m already off script here in my first sentence. So you’ve revised one of the books that you’ve written and very graciously provided me with a pre-release copy. So I was going through that prepping for the show a little bit to keep it on track of like, okay, there’s a thousand things we could talk about. Let’s talk about some specific things as we’re going to dig into some of those and a bit of the thinking behind the book. But one of the themes that’s in the book, and I think it’s just maybe part of who you are and what you like to do, it’s just sometimes things go wrong.

Michael: Sometimes things go wrong. Yeah, no, it’s a recurring theme of always thinking about what to do when it goes wrong. But actually the real, real interesting thing to me is also like, huh, how do we make sure this never happens again? Because so much of leadership is you get rewarded for the diving save or working the weekends or yada yada. That’s all because you screwed up. Something happened earlier. When you do the heroics and save the day, we screwed up. We’re all celebrating it, but someone screwed up, whether that’s planning or leadership or something. So it’s like, cool, how do we make sure that never happens? And it’s weird. It’s in a weird incentive cycle because no one claps when nothing happens.

Allen: Yeah. Oh man.

Michael: Right. They’re like, “Cool, everything went well. Awesome. Okay, great. So where’s the parade for nothing?”

Allen: It’s one of the worst feedback or lack of feedback loops in, I mean any industry in any job, but certainly in our job, is that exactly the thing. It’s working in a security job. It’s like, “All right, I guess it was secure because nothing… we don’t know of having been hacked.”

Michael: Right, right. And we love stimulus, we love stories and drama, and when it’s all just going smoothly, you’re like, “Cool.” You’re kind of waiting for it to blow up, but maybe you’re just doing a great job.

Allen: Yes. Or maybe you don’t know about what’s going wrong and… yeah.

Michael: Or even, oh my God, that’s the nightmare. It’s like it’s actually going wrong and you have no idea. That’s the nightmare scenario.

Allen: Which is the other thread that I pick up through. I mean you’re writing in general in the book, in particular is how to figure out if something is going wrong aka information flow in an organization, which we’ll end up talking a little bit about as well. And so before I briefly get back on script, just to give you an opportunity to the degree you want to kind of recap, I think probably a lot of folks are familiar with some pieces at least of your writing and your story, but how do you like to soundbite the Lopp story so far from your perspective?

Michael: Yeah, that’s a great question. I should be able to… I don’t know. I am back at Apple, which is sort of an interesting thing about me is I’ve always kind of gone forward and I’ve gone through a lot of different companies like Netscape and startups and Pinterest and Slack and then back to Apple. I think one thing is I’m a very curious person and probably I have the attention span of a mosquito is probably another thing to know about me, which means I’m always kind of interested in the puzzle and how to figure it out, whether that’s in my current gig or whatever, a problem that’s in front of me, this sort of thing. So you look at my background, it’s kind of this always forward, but I’m back at Apple. Why is that? Well, Apple’s great and we’re not going to talk about Apple, but I really like the philosophy of how we build there and the puzzles that we solve and also just obviously the impact of the things that are built there are obviously galaxy wide, so that’s a lot of fun as well. But I’m a curious problem solver is probably the headline, I just came up with a little coffee in me. And when I’m not doing that, I’m kind of unsatisfied. And also… sorry, I’m all over the place here. I think it’s super important. I believe when I started writing about leadership and stuff is to write these things down because when I was a first time leader, there was nothing. I wasn’t even surviving. I was just screwing it up left and right. I was looking for sort of materials and support and it’s one of the curses of tech is like, “Great, you’re now some engineer and you like people and you get along with folks, you’re a leader,” and you’re like, “Okay, cool, thanks. This feels like a thing. And what do I do?” And they’re like, “Well, do one-on-ones.” I’m like, “Great, what’s a one-on-one?” So writing it down for me was really one of the ways to figure it out, but also to share the lessons and kind of build the playbook. So that’s kind of a random set of things about me.

Allen: No, I mean it seems pretty representative from what I know about you and there’s a bunch of threads that I could follow on that. I should say a topic has come up a couple of times in the show and I’ve written a bit about and you’ve written about just kind of emphasize the value of that writing down loop. A lot of people tell themselves, “Well, who am I to write about this thing?” Or, “I’m not a writer.” And certainly I had that mindset for a long time. And your career, not to say that your career is built entirely on having written, but I imagine it probably was helpful in letting people up there in the world who had these career opportunities, know that you both knew some of this stuff, but also that you could think clearly about it and how you thought about that stuff. And it’s been helpful for me as well.

Michael: And thinking clearly, just to interrupt you, is actually the thing that I think writing does because you have this feeling about one-on-ones or leadership or problem solving or whatever the topic is, for me, the craft or the art of writing it down, passing it through your fingers, it requires you to sort of focus it and turn it into something that is more real than just that feeling you have. And you and I, you’re like, “Hey, what should we do about this thing?” I’m like, “Blah, blah, blah, blah.” And I’m like, “Well, that sounds like a philosophy. That sounds like there’s a rule there.” So then I start writing it down and I’m like, “Ooh, there’s a lot of structure and thoughtfulness or more detail to this that I didn’t know when I was sort of intuitively telling you the thing.” So writing it down for me, it makes it available to other people, but also it makes me very clear about how I feel about the thing, and that’s important. It makes me smarter in my head because I didn’t just YOLO it. I actually can tell you, I can defend this thing as opposed to just sounding like I know what I’m talking about.

Allen: Right. Which is very easy to just do through sheer confidence and force of will and lead everyone off a cliff.

Michael: Exactly. And people do that amazingly well, that’s super annoying. And they’re right too. And that’s even doubling. You’re like, “Ah, shooting from the hip and you’re correct. Dammit.”

Allen: Some of us need to actually think through a thing and go through the arduous process of turning it into writing. But another thing I really enjoy about that, and I’m curious if this resonates with you, is that when I write something out, that also lets me then criticize my own thinking, which is part of that process. Then so I go back and I read things that I wrote. I wrote a thing a few years ago about titles and levels when I was still… before I’d really designed a system for that, but I sort of just was learning and kind of repeating what I had thought I knew, and now I’m like, “I need to pull this post or redo this post,” and it lets me see what was wrong about that mindset.

Michael: And that’s one of the things we will get to the redo of the book is I’ve been lucky enough to… I did four editions of the first book and now the second book, which we’ll talk about this later, I didn’t think was good, but going through it and seeing it all, A, I found stuff that was really good. I’m like, “Wow, this is great.” And I kind of discounted the whole book. So I was ignoring it and I’m like, “Oh, this a bunch of stuff, that’s good.” But also I have changed, I’ve changed as a leader, I’ve changed in my experience and I’m like, “Okay, these four chapters are just gone. I don’t even believe this anymore. I’m embarrassed it exists and I got to go and change it.” And then there’s the more subtle, this thought is kind of 80% right, but I know I’m a little more mature or a little more thoughtful about this. So that ability to kind of update it over time is another privilege that I have.

Allen: Yeah. So let’s talk a little bit about that. So the book was titled Being Geek, or at least that was the main title and then it had the subtitle, and I can totally empathize or it makes sense to me that you would sort of over time, especially as you get further and further in this leadership now executive path and you have this book title and you’re like, “Well, out of any book title I could have, what is the most important things I would share? It is about being a geek or is it about leading humans and building people’s careers and building products and softwares?” That’s probably where your, I don’t know, heart and soul is of writing. Sorry, I’m telling your side of the story, but tell me a little bit of that process and then getting to now where book… the new version is going to be.

Michael: Yeah, so like I said, I didn’t like it that much. My heart was in… I’d written this book called Managing Humans, and it was doing well, but I’m like, “I got to do something else.” So conceit or the idea was like, cool, let’s describe this nerd, geek mindset in terms of a professional means, but kind allowing people to be comfortable in their nerd and geek skin, which sounds like an okay idea, but I wrote maybe a third of that book that I just described to you. And then I got behind, and also I tend to focus on these leadership topics. So two thirds of it was basically you could replace the word geek with leader and it’s a better book. Because I was talking about leaders, but I was trying to pull this nerd geek thing out of it. And it kind of worked, but it didn’t really work. So what I did, again, I told you I didn’t like the book. People talk about Managing Humans and dah, dah, dah, and I’m like, “Oh, this is working.” And then someone on my Rands Leadership Slack was like, “No, this is really good. I like this, this and this.” I’m like, “No, that’s garbage.” And I read it, I’m like, “Oh no, this is good.” “When you’re going to do a second edition?” I’m like, “I don’t think I would do it in a traditional way,” which is why I took the subtitle and made it the title Software Developer Careers Handbook, which is a mouthful, but it’s much more what that book is about as you already said. And I got to kind of cauterize all the geek stuff at it, but that didn’t mean I was deleting the chapters. I did exactly what I was told, like blah, blah, blah, blah, blah geek. I’m like, “Manager, leader.” And it’s better because that’s what I was actually writing about. So it was that transformation of maybe two thirds of it was edited and a third of it was duped and a third, that third was replaced with a bunch of new chapters as well. It’s a big book. I just saw it. I’m like, “Wow.” After my third book, Art of Leadership, which was kind of pamphlety in my head, this one’s hunkering, which I like, I don’t know, I like printing, I like books in my hand and I like to read books from the atomic perspective, not the bits perspective.

Allen: Yeah, it’s interesting that you say that because as someone who has not written a book but occasionally dares to contemplate doing it at one point, my instinct is like, “Man, the longer it is, the more chance for payroll,” in terms of things like you said, you get a third of the way through and then you end up having to something.

Michael: But I cheat because you’ve read it now or you’ve skimmed it. They’re independent things. So this work of a coherent 400 page arc is not necessary. I have these sort of chunks that I can do and I tie it together more and more, but it does a lot of flexibility. It is a lot of work in terms of the total amount of work, but someone who is writing some epic fictional thing where they got a title all together, that’s a nightmare for me. I panicked even just looking at you and thinking about it going, “Oh my God, how did they even do that?”

Allen: And the way that you’ve done the book, I don’t want to spend too long on the meta of, it’s just interesting to me because I look at my blog post stuff I’ve written and think like, “There might be something that this could get turned into.” There is an instinctual thing, and I imagine you have this, and I’m sure some people suggest it as like, “Oh, I should pull all of this writing. I have a part into pieces on the bench, and then try to build it into a coherent narrative with the beginning, middle, and end with concepts that build in linear order. And then eight years later, I have…”

Michael: You’re stressing me out.

Allen: I’m stressing myself out. But the book is a collection effectively, or I’m not sure exactly how you phrase it, but it’s a collection of stories, essays, observations, things that you’ve learned about this stuff. And so let’s dig into a couple of them.

Michael: Sure.

Allen: One of the ones that I believe most of these… I’ve probably seen a lot of the versions of them as blog posts, and then you get to think about it again in a new updated way or whatever you see in the book is this idea of if you’re not growing, you’re dying, which is…

Michael: Yeah.

Allen: We’re getting right in there, which is a topic that pulled out to me as a good place to start just because it’s something that’s come up on the show a couple times because it’s good career advice I think. I mean, there’s some people who… there’s some controversies you can imagine taking it too far. But I think if you’re growing, that’s good and I think that that’s going to build your career and that’s pretty intuitive. Something that question that popped out for me and maybe that some of this episode will just end up being Allen’s Q&A of trying to then build off of things that I learned in the book, but it made me kind of curious because we’ve talked about it on the show. How do you think about that if you’re not growing, you’re dying mindset? Obviously we want to apply it to ourselves if we want to grow our careers. How do you apply it to the folks that you’re responsible for, the teams that report to you? Is that something… do you think of it as this is an opportunity of motivating people or is it kind of like, “Hey, if we’re going to be high performers, you got to be growing. And if you stop growing, you might think you’re performing, but are you even fully…” Where do you sit on that spectrum of how you think about it?

Michael: I had this admin at a prior… this is related, I’m talking about an admin who works for me. And she was amazing and I was traveling a lot and the operational schedule for me was just a nightmare. Like, “Oh, hey, get on a plane, fly to Australia.” “When?” “Tomorrow.” I’m like, “Oh, sweet, cool. Can you handle that, Carrie?” What does this have to do with growing? We were doing a review and she was… I’ve never been an admin. I’m like, I’m giving advice from my perspective of how we’re working together, but my standard question is kind of what do you want to be when you grow up is my opening question. And everyone always smiles a little bit when they hear that question because it’s sort of playful, but I’m trying to look for something about how do you operate and how do I motivate you? To this day, I remember this, she’s like, “I like cash. I am coin operated.” And it sounds silly, but that was her thing. She was like, “I really would like to… that’s my thing. I’m interested in growth and promotions and more dollar dollar bills.” It’s silly. It was sort of a trivial way to describe it, but she did. That’s what she wanted. And every time that I’m sort of like, “Cool, should I get her a gift? No, actually she just wants a bonus.” There was a moment… that was the thing. And the thing for me and my team less… more seriously is everybody has that thing that I just described about what are they operated by, what is the thing that is motivating them? And some of them are… some folks just love the traveling. And so I have this thing that is sort of their motivator and I’m not sitting there and dangling it in front of them, but I’m searching for that thing that… and some of it’s promotion to the next role or some of it’s whatever it is, until I find that, I’m kind of a little at unease with the person because I’m like, “How do I frame this feedback or these goals relative to the thing that they actually want to do?” And it’s always there and it is the thing that they’re growing on, or whether that’s financial or motivational or experience or whatever the heck it is. So that’s number one is how do I find that thing that I can… their motivator so that I can figure out what the growth plan is. Because once I know what that thing is, whatever it is, I know how to give them goals, opportunities, rewards, that they can go and say, “Great, I’m motivated by this. This is the thing I want to do. So I am responsible.” And in my head, Allen always, I’m always… once I know it, I’m always thinking about that thing for that person because I never know when I can land a good piece of advice or this opportunity shows up. I don’t know when that’s going to… sometimes it’s completely improvisational, like, “Ooh, this is the time to tell that story,” or, “Oh, there’s this opportunity here that came out of nowhere that I can put her or him on.” So that’s the thing that I’m doing to keep them growing is to find that thing that’s going to motivate them exponentially more than other things. Does that make sense?

Allen: Yeah, it does. And I feel like you’ve answered the question I asked by immediately focusing… I said, “You think more A or B?” And then you could tell a story about A, and then you tell a bunch more about A, so I think in your answer, you think of it as a motivational tool rather than strict threat almost like “If you’re not growing, you’re dying, so I better see growth otherwise you’re all…”

Michael: Let me invert it and maybe answer a different version of this. To me, we’re in tech, I don’t know where AI fever is in your world right now, but six months ago I was counting the number of times it came up over the course of a couple of meetings. People would like, “Blah, blah, blah, ChatGPT.” It was bonkers. And it’s a function of this industry that we’re in is we’re seeking what is the new thing. And I don’t know about you, but I am deathly afraid of just the world is zipping on by and suddenly everyone’s talking about blah, blah, blah, programming language. And I’m like, “I’m sorry, what?” And this has been my entire life, is sort of always trying to find the new thing that is interesting, both because I’m curious, but also there’s fear there of being left behind. So that’s the sort of negative version of grow or die. But look at my career. We’re consumer software, enterprise software, security, consumer. Again, it’s kind of all over the place and it’s because I am sort of advertising at Pinterest, it’s because I’m curious, but I’m also wanting to stay on the… ahead of the wave if you will.

Allen: Yeah. For sure. That makes a lot of sense. There’s the underlying thing which we’ve again talked about in the show a bit, which is technology is completely outdating everything you know constantly. That’s why we love people like you and I who have this attention span that does not necessarily… as long as maybe sometimes we’d want it to be. And so that can be a weakness maybe in some fields, is a strength because that we sort of naturally think that way. And I think building that mindset is super helpful.

Michael: I agree completely.

Allen: So jumping to another section that I am excited to talk about. Presentations. I know that you think about this and you’ve done a lot of presentations. It’s something that I find really interesting about the art of it and also the engineering of it. So let’s pull a couple threads on there. Beginner mode first. What’s a presentation tip? There’s a bunch of stuff you talk about in the book, there’s lots of stuff you’ve talked about in… I think one time in Ireland you were showing me the test slide you had and how you calibrated and stuff like that. I’m sure there’s a hundred things you could talk about. But is there a presentation tip or approach that you found has been particularly helpful for people who are nervous about or just getting into giving presentations that they want to let help level up their career and they’re like, “I feel like I suck at this or whatever,” if you can kind of be like, “Oh, here’s something that’s been particularly helpful for people”?

Michael: This is the answer no one wants to hear, but let’s start with the number one thing. It’s not a presentation, it’s entertainment. It’s entertainment. And I don’t mean that in a negative way at all. I mean that you are there to entertain folks and yes, it’s a informational topic about whatever the heck the thing is, but let’s remember that piece. You’re up there to entertain, not to read your slides or not to stare at your shoes and kind of remember your script. I know as a nerd, as an introvert, that’s what I want to do. I want to hide and let’s get it over as quickly as possible. But there’s entertainment and I think they see themselves up there. This is me up there. This is the thing that everyone always says. They want to see you succeed because they’re kind of up there with empathy for you going like, “Wow, that must be hard.” So the beginner tip is you just have to practice it so much that you really have… let’s just say it’s a 20 minute talk. You’ve got to have 14 solid minutes or just in your head, and yes, you can use speaker notes and dah, dah, dah. You need to be able to tell the story and you need to be 80% confident in it because, and this is the hard part, and maybe this is a less of a beginner tip. 20%, it’s completely improvisational. Whether it’s something that happens or someone says something or something happens, whatever. Or you stumble on something that’s funny and you get this laugh that you’re like, “Oh, I didn’t know that was funny.” And now you go in callbacks to it, there’s something there every time, which makes it organic and fun and it kind of takes away your stress because you’re so comfortable with that background 80% narrative that you can kind of riff on and then do stuff. That’s the thing you want to get to. And it means practicing it 50 times, a lot and talking to nobody and maybe talking to someone and trying it, but you want to just have that feel of it in your head. And by the way, I do a ton of my editing during that as well. I say it, I’m like, “That doesn’t make sense.” The order is there or the energy is kind of going down and I want it to be going up or whatever it is. So I find a lot of editing it. But it’s practice, practice, practice, but not practice to rote. It’s practice to comfort so that you can jam and be entertaining.

Allen: Practice to comfort. I like that phrasing. My go-to phrasing and I find it entertaining that your go-to thing that you first thought, what’s your top thing, is the same thing I do. What I say is practice out loud excessively.

Michael: Yeah, absolutely.

Allen: I didn’t fully absorb that. I did that mostly just out of fear of, “I’m going to screw it up.” And so I practice, practice, practice just because I wanted everything to be perfect. A few years ago I was giving talk at a conference where the projector died mid-talk and instead of showing my slides, it showed the three ViewSonic birds. If you’ve ever seen the ViewSonic logo, there’s like three birds looking up. But I had practiced so much that I was just able to keep giving the presentation and joking about it and sort of describing it like, “As you’ll see in this three birds, the graph goes up into the right. It’s labeled, well-“

Michael: That’s improv, yeah.

Allen: And it was not obviously planned. Because I would’ve definitely preferred the slides to come back, but I had practiced so much that none of my brain was needed to keep moving. And obviously that’s not going to happen your first time you give your presentation, but I think it’s-

Michael: You don’t know though.

Allen: Maybe. I meant that level of comfort. The tech failure will happen, your first presentation, sorry, just let’s prep for you in advance.

Michael: I had one of my disaster ones that I was giving a talk. I was the keynote, I was the first speaker and they had gone el cheapo on the AV. So they set up that morning and they were still knocking out the kinks. So I’m up there and my mic starts dropping. So I’m like, “Hey, welcome to…”

Allen: Yeah. Oh man.

Michael: And it was like the first three rows could hear me, but no one else could. And so they’re panicking and I want to stay up. So I start yelling my talk with a dude on my belt trying to fix the thing. And by the way, this was the comfort thing. I’m like, I know this talk and this guy’s sitting here right here going… and I’m like… I’m kind of acknowledging him every now and then. Because it took three to five minutes to fix, but it still has kept going. But that was the same thing. It was just like, “I have to do this. I’m going to go with it. And I have so much comfort with the material and this is a talk.” I mean probably I have talks that I’ve done 50 times, so I could start right now and do it, but that’s getting to that state that it’s in your head and you can jam on it and riff on it.

Allen: Yeah, I love it. All right, so that’s the beginner mode question. Now I have a question that I want to know the answer to.

Michael: Yeah, yeah, totally.

Allen: So there’s a whole bunch of… like this thing, practice excessively or don’t read from your slides. So maybe try not to even have words on your slides. There’s a bunch of just things that we know generally makes presentations better and you try to do as much of those things as you can. But there’s also different contexts for a presentation. The lead dev conference is not the TED conference, which is not the presentation to the board of directors. And the presentation to the board of directors of a startup is not a presentation to the board of Apple or whatever. So how do you think about the different contexts and modes for presentation and what are the things that you vary as opposed to the things… maybe ignore the things that are always the same. What are the things that you maybe would adjust depending on that context?

Michael: I think the line that just popped in my head is sort of read the room, which is I repeat a lot of talks. This was years ago. I used to make a new talk for every time. This is a disaster and it’s incredibly huge amount of work. But I’m like-

Allen: We call that low ROI.

Michael: So now I have ones…. and by the way, I probably have 10 right now of which three or four are sort of the active rotation and I’ll sometimes go back, but they kind of age out over time. So to your question though, I’m doing a keynote for a company of 5,000 people. I’m doing the same talk for a cozy 30 people. It’s the same content, but there’s this ream that read the room factor of, I always ask them, “Who am I talking to? What are your challenges? What’s going on here?” And that is both selecting the talk as well as kind of changing the tone or the vibe of what I’m… or even some of the content to kind of say, “Oh cool, they’re working on rapid growth. I’ve done that. So let’s focus on the rapid growth piece.” So there’s that piece in terms of just understanding what talk they need and what version of the talk that they need. I mean there’s a lot of spectrum in the one you just talked about from the board of directors to small little YOLO whatever. I am me. I did a presentation to some important people recently and it was supposed to be a very buttoned up strategic talk and I was just like, “I’m going to have a little fun with this.” Because that’s kind of how I am and I want to be a little light even though we’re talking about something very, very important. So there’s a certain amount of, “Yes, I want to read the room and adapt to it,” but there’s also a certain voice that I have as me, Michael Lopp or Rands or whatever my name is, that you should come to expect even though whether it’s a staff meeting presentation or a keynote or whatever it is, there’s something that is always me and it’s maybe a comfort thing or just where my center of gravity is as a presenter. But that’s kind of how I roll too. There’s a bit of adaptation, but there’s not too much, I’m not totally turning into professional board of directors talker. I mean I can do that, but it’s a little bit of both.

Allen: Yeah, I like hearing that. I think people imagine these contexts where they’ve never presented as maybe requiring them to be someone who they’re not. Oh, if I was to ever give a TED talk, if I was to present a board of directors, well that’s not the person I am. But once you get that opportunity, often you can probably… you are the person who was invited to do that.

Michael: Yeah, exactly. But yeah, I mean it is true. You want to read the room is a big thing for me, not just from a presentation perspective, but even us talking right now. And anytime in a group of folks I’m kind like, “Hmm, what hand have I been dealt here?” And I am quickly figuring it out because probably a little bit on the spectrum to understand the situation I’m in and also want to kind of mimic, and I don’t mean any negative way to kind of like, “Oh, cool, this is what this vibe is here,” so that’s important to me. That’s comforting for me.

Allen: Yeah, adapt to where you are.

Michael: Exactly. Exactly.

Allen: So that flows into related thing, but interestingly in the book you crystallized something that I’d known but I’d never been able to say, and now I can say it because you highlighted it, which is demos and how a demo done well, an internal demo where you’re trying to show your work, is not the same as a presentation. Or you describe it as an information gathering exercise, which I found is of course it is, but I would never have been able to come up with those words. I’d be like, “Yeah, you make a presentation about what you demoed.” Talk about that a little bit and what you see as what goes into a successful demo.

Michael: The tweets… sorry, are we calling them tweets anymore? The tweet?

Allen: Yeah, the post.

Michael: The post. God, what a bad idea. It’s such a good word. And now we now feel guilty even saying it, little meta commentary there. The pithy, the little thing about a demo for me is I can sit here and say, “Hey, I want to do this feature.” I say, “It’s going to do this,” and you swipe that and you’re kind of like, “Oh, I can kind of imagine that. And do you mean this?” And I’m like, “Yeah, that.” And you’re like, “Well that’s cool.” And then a button here and this does this and this flow kicks in. You’re like, “Yeah, totally.” I’m like, “Great, cool. Thanks for the feedback.” As opposed to me doing exactly the same thing where I put together a prototype or a demo and I give it to you and you can use it. The quality of the feedback when you give someone truly something real that they can react to is night and day. Everything that I talked about in that first thing is just you and I jamming. And by the way, you’re picturing something completely wrong in your head. We’re agreeing the words are the same, but you’re like, I said slide and you were thinking slider, but I was thinking this other whole of-

Allen: Whole screen sliding or something.

Michael: Right, exactly. Whatever. That is a night and day difference in this hypothetical product that we are talking about here. Versus I give it to you and I say, “Okay, cool, it’s this. Tell me what you think.” And you’re like, “Du, du, du.” And I’m watching you use it. By the way, watching you use it without you saying anything. I’m like, “Oh wow, that’s the first thing you clicked? Never in a million years did we predict that at all.” And so we’re like, “Okay, that’s interesting.” And I haven’t even asked you a question yet. So that’s the core of it is give them something real to react to, to understand what is their reaction to it. That’s a hands-on demo. But the demo is the same thing as well, which is just putting it on the screen and you can’t even use it. And seeing it is so much different than scribbles and little drawings or just the words that we’re using there. So that’s the core thing is the quality of the feedback is so much better when there’s something real that they can see and hopefully touch.

Allen: And this idea of demo as an information gathering exercise kind of flows. And I guess sort of pulling apart a little bit more, there’s categories of presentation effectively that are also that. Sometimes when you’re presenting, “Here’s how to make great docs that your team will actually read.” It’s not an information gathering exercise. You feel like you know the thing, someone invited you to talk about the thing to the team that wants to know the thing. But if you’re like, “Here are three ways we could approach this. And I need to understand which of these has dragons behind them,” that’s also maybe an information gathering exercise too.

Michael: Right. Yeah, absolutely. Even in that scenario where you’re in early days, even just the scribbles on paper are better, like, “Hey, by the way, is it A, B or C? What do you think? Let’s do that.” That’s better than, “Hey, I’m kind of thinking this thing, dah, dah, dah.” It’s the visual thing to react to, which I think is just… because you’re building a product for humans that they’re going to touch I think is the key.

Allen: Yes, I love it. And that’s one of the things I’ve been trying to build over the last year especially, is I try to be more thoughtful about information gathering and not letting certain habits to make it seem like I am going to have one directional information flow here, which it’s easy to do. Oh, I think of it as a presentation, so I’m just blahing at you and wasting an opportunity.

Michael: Well, it’s similar thing for writing. Let me pivot over to writing again, is early writer, early presentation, I was like, “Cool. Just get it done and get it out there and I’m good to go.” And I wouldn’t let anyone see it because I was terrified by the feedback, by the way. Terrified. This is early on in my writing career. Someone mailed me and she said, “Hey, I love your stuff. You’re not letting anyone edit it and your thoughts are worthy of someone spending some time, not you doing the editing process.” And it wasn’t just copy editing. That was certainly a part of it. If you go read the early stuff, it’s horrifically bad. Thank you, Grammarly. But it was also just like, “Hey, I know you’re trying to say this, but you’re doing 3, 1, 2 and it should be 1, 2, 3. Do you see what I’m saying?” And I’m like, “Yeah.” And if someone had just said that to me, I’d be like, “Of course, you’re right,” in a safe way in feedback. But that’s another thing is that ideas always… I mean even with a author writing a book, he or she’s getting all of this other feedback and it’s making it vastly better. Yes, it’s still the core story, but the eyeballs on the idea always make it better.

Allen: And for a book, obviously assumption is that you’re having an editor and they’re helping with that. When you’re writing blog posts, what does that editing loop look like? Do you have just a couple of trusted humans that you send drafts to and there’s people that you know and they help you out with that kind of thing?

Michael: I’m confident enough along with a copy editing pass that I will solo yolo it, but if it’s something which is kind of big and I’m like, “Hmm, what am I thinking about it,” I’ll get a first draft and I’ll give it to someone. But there’s another thing that’s important is I write something and I have something right here, this piece that I’m working on right this moment.

Allen: Real paper.

Michael: Real paper. Well, I print… well, you’re going to hear about this. So I wrote it in Bear, my favorite tool for writing, and then it’s like half done I’d say, but I’m like, “Hmm, I’m not sure where this is going. I like it a lot.” So I do two things. I print it out and I also give myself one to three days of not thinking about it at all because that return, once the cache has been purged and I go back in, I can refeel how I feel about the piece in a way that if I’m in the middle of it, I’m too close to how the sausages are being made. So I’m kind of echoing the thing I’ve already… there’s a reset. So that’s another piece there is giving your brain time to get away from it. My wife and I are playing Wordle religiously as everyone was doing for the last three years, and there’s this thing she did, she was playing once and she was like, “I don’t know,” three steps in and spiraling. I just put her phone down, going to not do this for a second, waited a couple minutes, talked to me about whatever, and she went back. Same thing. It’s this purge and this sort of cleansing of the perspective to go back in and of course she got it a minute later because she’s this Wordle champion. That’s a hard thing to do when you’re sitting there and you’re trying to solve the problem or write the thing or whatever it is, that stepping about piece. But I find a lot of great edits come from distance and from being away from it as well.

Allen: Yes, one of my habits that is one of those kind of, I feel like this is a bad wasteful habit, but also it’s idiosyncratic and it works. So I’ve kept doing it, is I’ll write in Bear and I’ll iterate and edit and hopefully start early enough that I go back and forth to it over multiple days and I’m not trying to crunch for my self-imposed deadline. But then even if I think it’s totally perfect, I will then load it into the CMS on my website, put a poll request, read it in the context of a different typeface and a different setup and different layout and the links are actual rendered instead of Markdown and then I’ll be like, “Oh, this has a bunch of problems.” Just because the context changed. That’s the printout idea, I guess.

Michael: That’s the printout thing and I also like the pen and crossing it out and I have a certain pen that I use, so there’s something to that which makes me… again, it’s a different context, it’s a different perspective that I’m applying to it. And another thing that this just takes years of it, words used to be precious. I’d be like, “Oh no, 180, 852 words and these are the ones.” It’s like this is your brand lying to you and being scared about feedback or whatever the hell. The words are infinite. Like, “Cool, let’s tear it up. Let’s start over again.” That’s a power move to be able to do that, but it is infinite now in my head because I’ve written so much.

Allen: And you’re confident that more words will flow eventually.

Michael: It hasn’t stopped or slowed down at all. It only increases actually the more that you get good at it, I have found.

Allen: Yeah, and hence then back to the beginning. I think we were talking in the very first few sentences of the show, try writing about the things you learn even if you don’t think that you should be.

Michael: Absolutely. Absolutely.

Allen: Before we went down on and ran out of time, there’s a couple things, another thread I’d pull from the book that I thought might make interesting kind of questions or things that I found myself wondering. So I think they would be interesting. One comes from this idea of you talk a bit about the no excuses mindset, which had come from a leader that you would work for and how if somebody was making an excuse that they would basically put a stop to that and say, “Hey, that’s not how we think about things here.” Which I certainly appreciate the value and how important it’s for people to take responsibility for how did I contribute to this thing and how could I contribute to helping fix it. You want to have an organization where people think that way. The thing that I found myself wanting to ask is how do you as a leader who’s trying to establish that culture on your team sort of distinguish in between the lines and the gray areas and between someone who’s making an excuse and trying to deflect responsibility for something versus someone who’s just trying to talk through how something came together and then from their perspective as far as they’ve been able to figure out so far, it wasn’t their fault.

Michael: I think you’ve already answered your very good question, which is a much bigger question than I think you realize. You just actually answered the question relative to excuses, but I have more to say. Because you just said the spectrum is number one is like, “Hey Allen, what happened here?” And you’re like, “Oh.” And I can tell from how you’re answering it, a couple of things. Maybe you don’t know, maybe you feel scared that you’re in trouble or whatever. And it is the deflection. It is the like, “Oh, well, if we had time because of schedules or this other team didn’t screw me, we’d be fine.” All of these words that I’m saying and the tone that I’m using is excusey and you’re nodding, so you agree with me. As opposed to the other end of the spectrum where they’re just trying to understand and there’s accountability in it. They’re like, “Yeah, there was these three bugs and we are still evaluating what’s going on here and I don’t truly understand it yet, but we’re working to figure out the root cause and what the smoking gun is and what’s going on there.” And I’m making these up, but you can even hear it in my voice that this latter one is this is my responsibility to figure out and I own this and I don’t know… and maybe I throw some theories out. Maybe the server team didn’t do this, but it’s not a throwing them under the bus or deflecting responsibility to them. It’s truly this act of understanding. But I want to step back a little bit to talk about the larger implication of your question, which is I think there’s a lot of humans that think that leaders have it all figured out because it says they’re like, “Cool, well he or she’s here so they must know.” And there’s this, well, they’re the accountable ones, so it’s kind of their responsibility to take the bullet if… whatever. If in a larger company you can feel very distant from what feels like the accountability of a thing. And let me be super clear, leaders are as fallible, as screwed up and I make as many mistakes as anybody else. I do have a different role and I am accountable. I am the person who was… but my job is to make you feel, and I don’t mean this in a negative way or in a dictatorial way, you are accountable for that thing. That’s yours, whatever that piece of the product or the technology or the stack is. And I encourage you to do that. And when you feel that that’s yours and you’re the responsible party who can explain it and defend it, it makes it less excusey. You feel empowered because you have ownership of that thing and actually you feel like… and you probably feel bad when something goes wrong, but it’s not feel bad in a throw someone under the bus sort of way. It’s just a, “I feel like this is good. Let’s figure out what’s going to go on here.” When people jump into the excuse mindset that you described really well at the beginning, there’s something wrong from a trust perspective or an ownership perspective or a team dynamic perspective because they’re mad, justifiably so, about something. I don’t even know what it is. There’s a million things. That it’s kind of a bug report to me about how I’m leading them or how the org is designed or how the product’s built or whatever. Because they don’t feel it’s theirs. They feel like it’s okay to be like, “Well, I don’t know, this is dah, dah, whatever it is.” So I’m kind of all over the place here. But what you’re talking about is a lot of different threads about being a good leader and having an effective team with really clear roles and responsibilities.

Allen: So there’s two pieces to what you said that I’ll pull from that. One is this just curiosity mindset versus blame mindset, which is of course huge leadership thing. As much as we can get onto the first of those two things, we’re going to have more effective teams, and so that’s great and that’s helpful and clarifying. And then there’s the other piece, which is the organizational design piece and the responsibility piece, which then now clarifies to me that it’s mindset of no excuses and the sense I’m getting from what you’re saying is that the thing you’re particularly interested in with that mindset is no excuses about the stuff that you’re responsible for. So if something that you’re totally not responsible for and it has nothing to do with you, breaks and someone asks you about it, you don’t have to just say, “Well, I guess I’m going to follow in some other person’s sword because no excuses. No idea how I could have possibly contributed to this.” But ideally, if you’re doing a good job of setting up your teams and communicating with the folks who report to you, they have a sense of what their scope of responsibility and what they’re accountable for is. And if there’s a disconnect in between the person who’s leading and the person who’s dealing with something that they feel like they can just sort of say, “Well, that’s not my… I’m not responsible for this kind of,” effectively.

Michael: Not my problem.

Allen: Yeah, not my problem. Then that’s kind of an urgent bug report on, I have not been clear. It is in fact at least somewhat your problem and we need to have some curiosity, accountability loops rather than some blame the server team loop.

Michael: Well, there’s another piece there that when I see the excuse mindset, I feel like I have failed because even if it is entirely some other team in the company’s problem, making fun of them or blaming them or throwing excuses at them, this is unhelpful stuff. This is actually politics and it’s one of the things I despise and it exists. There’s good politics about it. It’s the bad politics. And for me, it goes back to something earlier we talked about, it’s sort of like when I’m looking at this problem and it’s entirely not my issue, it’s somehow affecting me, but it’s like 90% somewhere else, I’m still coming at it from a, “Well, that’s curious. What’s going on there?” Not in a, “Oh boy, that team has screwed it.” I’m like, “Wow, that must be hard.” And I feel very neutral about it. I mean, not neutral, but I feel very not drama-y about it because humans love drama. They love the gossip and they love to say, “Oh, did you hear du and du was totally screwed. And I know that and now you do, so I’m better.” To me, it’s sort of like, “Wow, that’s such a hard problem they have. How are they going to solve that?” That’s how I think about the world, both on how I like to understand things, but also I’m not putting any drama into the soup. I’m not gossiping about the team or saying they’re screwed or anything like that. I’m leading with this sort of like… and maybe there’s a way we can help them. Maybe there’s something we should be doing differently. I don’t know. It’s all hypothetical and kind of a little slippery, but that’s how I view it and I want my team to see me do that because I want them to do that about their peers and those teams they support and the people around them.

Allen: I love that perspective on it and I think it really emphasizes one of those things about building a good team and culture in organization, which is that the curiosity is so… it bears so much fruit. Because certainly to your point, it reduces the instinct that we all have to gossip about how screwed up this team is and how they must be so dysfunctional. How could they possibly have this problem or still be failing? So certainly that just adds negativity and toxicity and all the stuff that you don’t want. But even ignoring all those effects, if you are curious about, “Wait a minute, but why are they still failing? What are the things…” Actually, now that I think about it, a billion users is a lot. Or whatever the contributing factor.

Michael: It’s hard to scale that really well without proper planning.

Allen: Yeah, it’s somewhat challenging or whatever the circumstance is, or maybe it’s like this seems like a straightforward problem and it’s like going in with a curiosity of what are the contributing factors, and even if you go in and then you learn, I’m like, “Oh, actually I see. They’re trying this thing and they’re set up that poorly in this way and this one person is responsible for 40 things or this person left,” or whatever the things that contributed to, then there really is dysfunction, it’s not just a really hard problem that people are actually doing very well at. Then you’re also learning things that you can then take forward into how you either interact with that team or build your team or all that kind of stuff, and it makes you a better team member leader.

Michael: To pull it all the way back to the beginning and the books and stuff is like, to me, the real joy is when I find a rule and there are always guidelines, there’s never rules because humans are chaotic, beautiful snowflakes and they’re always different. But there are rules or guidelines or principles to find and sometimes you’re like, “Oh, uh-huh. Uh-huh. Oh, this is always this way. This is what happens in this case, with this set of people or in this technology set up or in this part of the product process.” And finding those things and writing them down and finding that wisdom, that’s the true joy because I have this totally unachievable belief that I’m going to figure it all out at some point. By the way, I’m not. But you can’t convince me otherwise because that’s what drives me is there’s the ultimate playbook that I will figure out at some point and be like, “Okay, here we… all right everybody. We’re done. Cool. Let’s go play some destiny. Everyone good? Great. Okay, here’s the playbook.”

Allen: Asymptotically achieving full understanding of human beings and how they work in groups.

Michael: We can do this.

Allen: It’s no big deal.

Michael: One more book and I’ll be done.

Allen: One more revision and then we’re like 80% of the way there. This has been an amazing conversation. There’s so many other things I could ask.

Michael: We could go for many hours.

Allen: But I’m going to be disciplined for now. Maybe have you back again sometime to dig into one of the various paths. So thank you so much for coming on the show. How can people find more about the book and you and your work in general?

Michael: There’s three things there. I’ve been writing at this blog, are we calling them blog still?

Allen: I guess we’re still calling that.

Michael: Rands in Repose, that’s been around for decades. I do a podcast too with a guy named Lyle called The Important Thing where some of the topics you and I just talked about show up there. But I think the most important thing, if someone is curious about leadership, the thing that… one of the things I’m most proud of is I got lucky. I was a VP of engineering at Slack. I have a Slack called the Rands Leadership Slack, which is about 30,000 or so folks, and it’s all people leaders, whether they’re interested in leadership or whether they’re in the middle of leadership and they’re just in there supporting each other. It’s one of the most helpful leadership utilities I had a chance to build. It’s mostly other people doing it now, but they should join that and see… get involved in that conversation. Also, we talk about other things like pens and watches and destiny too.

Allen: So I will link all three of those things as well as the book in the show notes for the show. Thanks a lot.

Michael: Thank you.

Allen: It Shipped That Way is brought to you by Steamclock software. If you’re a growing business and your customers need a really nice mobile app, get in touch with Steamclock. That’s it for today. You can give us feedback, follow us on social media or rate the show by going to itshipped.fm/contact. Let us know what you think. Until next time, keep shipping.

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