Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
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Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Finally. I want to start with a little bit of context. So I always find that finding one's love in life is actually quite rare. Many people don't actually find their love. And so I wanted to start on yours. When did you first fall in love with product and tech? And can you take me to that moment?
A It's, I think love's a good word. I think, I think we, we use that word kind of, we throw it around, but I, I think love is a good word to describing where I'm at and I'll tell you why. So I got into computery things through, uh, fine arts in high school. So we're going back to 1988. I'm in high school and I, there's too many things I like doing. So I picked, I'm going to do fine arts and music and math. And I ignored everything in between. I've never taken any biology class. I've never taken any history. I did literally did fine arts, music and math. So my days were, you know, drawing and painting, music, band class. And then I did, I did math. And then at one year I told the band, Leader, I said, hey, my parents got me a computer, and it turns out that there's this protocol called MIDI, and I can, I have a keyboard, and I know we're doing a Phantom of the Opera Les Miserables mix, what if I did all the music for it? Like myself, you don't need the band. And she was like, that's crazy, and I was like, I was like, I think I can pull it off. So I used this program called Cubase, like version 1.1 in 1988, and um, I guess this is way before AI, but I basically Fired the high school band, and they didn't have to do anything for the whole musical that year, and I pulled off, um, uh, Les Mis, Phantom of the Opera medley, uh, with my computer and my keyboard, and I, I recorded, you kn…
AI assessment note: “I used this program called Cubase, like version 1.1 in 1988”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And, um, I think it was, uh, Is it a bit of being everything to everyone? Landing the biggest brands in the world, landing Kim Kardashian, landing X and Y, but then also wanting mum and pop shop. Who's got a bakery and actually you start.
A Absolutely. But you know what is we found the similarities between them? So that's actually like, okay, let's peek into Shopify's product strategy was exactly that, right? So if you take all the retailers on the planet, right. And you organize them maybe as a bit more like a triangle, right? So there's complexity. There's, and there's volume. Okay. Actually, if you, if you draw a line and you don't, you just look at complexity and volume, right? What you realize is that high volume and low volume merchants are often low complexity. And you're like, oh, holy shit. They've got something in common. They're low complexity. What does low complexity for retail looks like? It's low skew count, right? Low, like just, they don't have a lot of individual, like, or not count, but low skew count. They, they're not selling, like, their, their, their catalog's not a million things. They've got one, one website, like, so a mom and pop shop and Kardashian have a lot in common. So what are the differences? Holy shit, Kardashian's gonna do 70, 70,000 checkouts a minute. Okay, let's, let's solve that. So that was our sales strategy. It was like, we found some commonalities in the platform regarding these small merchants and large merchants have an 80% overlap. Let's fix the gap so that the, the, the super, super large ones You know, don't crash. We've got highest volume. Go out. Let's go after Su…
AI assessment note: “a mom and pop shop and Kardashian have a lot in common.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Do you care if they've had experience in the industry? Oh, well, you know, you've, you've got experience building developer tools before, ah, you've got experience in, you know, e-commerce and fulfillment or whatever, maybe the kind of chosen field. Do you care about experience or do you go, no, it doesn't matter?
A Generally not. I think the, those three-step process for questioning is really about getting to know that human, right? About what motivates them, what their will is, what their skill is. And do I think that they can grow? You know, like those three things, right, are, are, because you're putting humans on like a, a growth trajectory of things and matching that with what your company is. Now, there are some, you know, you're building a logistics company, like it'd be good to someone who's been in a warehouse before, like there is some advantage of doing that, but I'd say there's, there's a lot of people you can just throw into the deep end, into, into anything, and they're gonna learn it, right? Um, and, um, so I, I, I want people who can grow quickly and people who can, um, Understand that problems are multi-layered and see that and fix it. I think that's more important.
AI assessment note: “Generally not.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q So we have so many operators that listen. When we think about that, do they then, like, what can they do to action that very specifically? Do they sit down with their team and say, hey, I would like a Slack every morning with A decision. A update. How can they action this and make that tangible?
A No, it has, it has to be a bit more natural than that, and I think there's, um, there's a book by Susan Scott where she introduces the decision tree, and the decision tree is basically how you talk to your team about this, and you go, hey, listen, there's roughly three types of decisions that we're all gonna make, right? There's root decisions, there's trunk decisions, and there's leaf decisions. Root decisions are kind of really important. They're, they might be one-way doors, they're hard to undo, right? Trunk decisions are, You know, medium size, you know, and then leafs are, they don't matter, right? So, like, let's talk about the roots together, and, and don't surprise me, right? Make sure that the trunks, we should bring, like, if you want to brainstorm, I'm always available for that, like, I always want to learn something from you, and maybe I can bring some input, and leafs, as you said, don't bug me about that, right? So, as you say, like, your, I think your approach of, like, I hired you big bucks, go away, I think I think is a bit naive in a sense, and maybe naive is not to worry, but it's, it's simplistic, right? Where I think building companies where there's a lot going on, there's a lot of micro decisions to be made that make a difference. You know, like, like sometimes like we're going to put the code there versus there. Sounds like I just trust you versus that's…
AI assessment note: “how you talk to your team about this, and you go”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q I, I agree completely. I, I'm, I'm thinking to something that you've actually said before though, when it comes to people and talent management, which is the worst advice is hire great people and get out of the way. I've, I've always believed that. And so can you help me understand why is that such bad advice?
A So the context here is everyone's heard of that phrase, right? I'm thinking like it must be written in like a bazillion Harvard management books, right? Like hire great people and get it either way. Um, you know, like, and I believed it. I was like, holy shit, like that's the most, like that makes so much sense, right? Because everyone's love, loves autonomy. You know, I'm like, just give people autonomy. And what I realized building companies is if you're trying to get a bunch of people together and have a shared understanding of what great looks like, it's messy to do that. Like there's no way you do that by letting people go in their own direction, right? Like there's, there's like a, I think the Steve jobs analogy, there's a rock tumbler that you're going to be in together to figure out how you're going to polish things, how you get a shared alignment. So, so for me, You know, hiring great people and get out of their way is like, is basically an, it is assuming that everyone is magically going to have the same understanding of the world, is magically going to have the same quality bar, is magically going to be aligned on how they do things, like is impossible to happen, right? So, um, so I think it's, it's not only do I think it's a bad, I've seen the biggest train wrecks in companies happen because bosses do that, or VPs or CEOs, they hire people and they let them run, and…
AI assessment note: “it is assuming that everyone is magically going to have the same understanding”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q were very good at it. And it led to like key, key leadership roles at Shopify, at Atlassian, which is obviously how you're so close to Harley and, um, Scott. I want to ask, they're very seismic organizations and they have big impacts on people's minds. How did, if you were to one takeaway from each on how it impacted your mindset, Shopify and Atlassian, what would it be Jean-Michel?
A Yeah, that's a good question. So from band class to, you know, Uh, leading and growing kind of the engineering organs at these two companies that at the time had no idea where they're, they're going to be so massive. Um, and seeing both from the inside, I'd say Shopify and Atlassian are really interesting. If you drew a Venn diagram of both companies, there's an overlap and there's a non-overlap of both. So the overlap is, um, and I, I learned from both is founders playing the long game and good at marketing. And that might be a bit weird coming from an engineering dude, but like founders playing the long game. So making these decisions that, you know, I guess staying alive long enough that you just. You know, you'll be around longer. Um, and they're both brilliant in marketing, right? Harley, Mike and Scott, like they, they knew the value of, of, of getting eyeballs. And as an engineer building things, I, I was kind of at the time when I, when I met all these folks, it was heads down, just trying to make things work, loving building companies, building teams together. But I think the value of investing and getting eyeballs was, um, something I learned from both.
AI assessment note: “I learned from both is founders playing the long game and good at marketing.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Do you care if they've had experience in the industry? Oh, well, you know, you've, you've got experience building developer tools before, ah, you've got experience in, you know, e-commerce and fulfillment or whatever, maybe the kind of chosen field. Do you care about experience or do you go, no, it doesn't matter?
A Generally not. I think the, those three-step process for questioning is really about getting to know that human, right? About what motivates them, what their will is, what their skill is. And do I think that they can grow? You know, like those three things, right, are, are, because you're putting humans on like a, a growth trajectory of things and matching that with what your company is. Now, there are some, you know, you're building a logistics company, like it'd be good to someone who's been in a warehouse before, like there is some advantage of doing that, but I'd say there's, there's a lot of people you can just throw into the deep end, into, into anything, and they're gonna learn it, right? Um, and, um, so I, I, I want people who can grow quickly and people who can, um, Understand that problems are multi-layered and see that and fix it. I think that's more important.
AI assessment note: “Generally not. I think the, those three-step process for questioning is really”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q So we have so many operators that listen. When we think about that, do they then, like, what can they do to action that very specifically? Do they sit down with their team and say, hey, I would like a Slack every morning with A decision. A update. How can they action this and make that tangible?
A No, it has, it has to be a bit more natural than that, and I think there's, um, there's a book by Susan Scott where she introduces the decision tree, and the decision tree is basically how you talk to your team about this, and you go, hey, listen, there's roughly three types of decisions that we're all gonna make, right? There's root decisions, there's trunk decisions, and there's leaf decisions. Root decisions are kind of really important. They're, they might be one-way doors, they're hard to undo, right? Trunk decisions are, You know, medium size, you know, and then leafs are, they don't matter, right? So, like, let's talk about the roots together, and, and don't surprise me, right? Make sure that the trunks, we should bring, like, if you want to brainstorm, I'm always available for that, like, I always want to learn something from you, and maybe I can bring some input, and leafs, as you said, don't bug me about that, right? So, as you say, like, your, I think your approach of, like, I hired you big bucks, go away, I think I think is a bit naive in a sense, and maybe naive is not to worry, but it's, it's simplistic, right? Where I think building companies where there's a lot going on, there's a lot of micro decisions to be made that make a difference. You know, like, like sometimes like we're going to put the code there versus there. Sounds like I just trust you versus that's…
AI assessment note: “there's a book by Susan Scott where she introduces the decision tree”
Answered raw tape
D 5 · C 5 · P 4 · Cm 3 4.45
Q I, I agree completely. I, I'm, I'm thinking to something that you've actually said before though, when it comes to people and talent management, which is the worst advice is hire great people and get out of the way. I've, I've always believed that. And so can you help me understand why is that such bad advice?
A So the context here is everyone's heard of that phrase, right? I'm thinking like it must be written in like a bazillion Harvard management books, right? Like hire great people and get it either way. Um, you know, like, and I believed it. I was like, holy shit, like that's the most, like that makes so much sense, right? Because everyone's love, loves autonomy. You know, I'm like, just give people autonomy. And what I realized building companies is if you're trying to get a bunch of people together and have a shared understanding of what great looks like, it's messy to do that. Like there's no way you do that by letting people go in their own direction, right? Like there's, there's like a, I think the Steve jobs analogy, there's a rock tumbler that you're going to be in together to figure out how you're going to polish things, how you get a shared alignment. So, so for me, You know, hiring great people and get out of their way is like, is basically an, it is assuming that everyone is magically going to have the same understanding of the world, is magically going to have the same quality bar, is magically going to be aligned on how they do things, like is impossible to happen, right? So, um, so I think it's, it's not only do I think it's a bad, I've seen the biggest train wrecks in companies happen because bosses do that, or VPs or CEOs, they hire people and they let them run, and…
AI assessment note: “is assuming that everyone is magically going to have the same understanding”
Answered raw tape
D 4 · C 5 · P 4 · Cm 4 4.30
Q were very good at it. And it led to like key, key leadership roles at Shopify, at Atlassian, which is obviously how you're so close to Harley and, um, Scott. I want to ask, they're very seismic organizations and they have big impacts on people's minds. How did, if you were to one takeaway from each on how it impacted your mindset, Shopify and Atlassian, what would it be Jean-Michel?
A Yeah, that's a good question. So from band class to, you know, Uh, leading and growing kind of the engineering organs at these two companies that at the time had no idea where they're, they're going to be so massive. Um, and seeing both from the inside, I'd say Shopify and Atlassian are really interesting. If you drew a Venn diagram of both companies, there's an overlap and there's a non-overlap of both. So the overlap is, um, and I, I learned from both is founders playing the long game and good at marketing. And that might be a bit weird coming from an engineering dude, but like founders playing the long game. So making these decisions that, you know, I guess staying alive long enough that you just. You know, you'll be around longer. Um, and they're both brilliant in marketing, right? Harley, Mike and Scott, like they, they knew the value of, of, of getting eyeballs. And as an engineer building things, I, I was kind of at the time when I, when I met all these folks, it was heads down, just trying to make things work, loving building companies, building teams together. But I think the value of investing and getting eyeballs was, um, something I learned from both.
AI assessment note: “value of investing and getting eyeballs was, um, something I learned from both.”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q So if we think about the two kind of different worlds that you mentioned, which was speed versus kind of quality, for founders again that listen that are in their first three years, say, we have, you know, 700,000 that listen, um, How should they think? Is speed of execution everything? Or is build slow, but build right the right way at that stage?
A Do both. That fits what you've got to do, you know, and I'm like, I'm in the middle of building. So I, you know, I did the shop fight lasting thing, hyperscale, and I've, I've done the one to N a lot, right? Which is the, after your product market fit, everything breaks. And how do you put the pieces back together and, and build a company and an organization to get to, you know, I'll, you know, hundred x that. Um, I haven't done the zero to one in a while, so one of the things I've been doing for the last year is a zero to one again, and just prove I can go back to band class and, and play my instruments, and uh, one of the, I'm, I'm living this viscerally right now, which is that debate of like speed versus quality, the good decision is every month pick, you know, half the things that have to be polished, like they're, like the best things on the planet, and half of them don't have to be. You know, and that's, and that's where you actually get long-term momentum, which is polish the things that you want. You know, you know, your customers are going to go, holy shit. Like I just use this app, blah, blah, and it's does X, Y, Z like amazingly. And then the other stuff, like, you know, they're not probably going to talk to their friends a bit. Right. So for me, that's the thing of just like every month there's like half I'm doing, I'm going to rush it. And in half I'm not. So the …
AI assessment note: “Do both. That fits what you've got to do”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q fluff. And it makes me think to one of your tweets, which I loved. You said, I've retired from software process, no scrum, DDs, TDD standups, a load of other things. Instead, we just build and run software together. Software teams are built on process, as you know. Why is that wrong? Why are you issuing that? Can you just talk to me about why you don't need it now?
A Yeah. And as you can tell, as we're talking, I'm, I'm probably overly maniacal about, um, waste, maybe put it that way. Right. Um, and you know, I think that I've been pulled into the whole, there's a process that's going to make me better. Right, like there's, there's a thing there, like there's a way I should be working that's going to be better, that's going to bring something out of me, and what I realized a lot of, you know, and, and a lot of this came out of like some of the last years at Shopify, you know, as I was, you know, programming the organization and trying to get the most out of people is, is, um, we put process in play, like you put process in place because you got people and, and, and some of it's there, but I, what I realized is, is At the end of the day, what just really mattered was like a couple of people making some really good decisions and, and that's writing code and, and, and getting like, it's almost like your architecture is your strategy. So I was like, why don't we spend more time talking about that versus who's doing what? And are we have, do we have story points? And, um, like one really, really good example is I, I believe that one of the things that slows teams down the most is what I call time horizon friction, right? So we, so if you think about slowing down, it's physics, right? Like there's some friction in place that's going to slow you d…
AI assessment note: “what just really mattered was like a couple of people making some really good decisions”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q So if we think about the two kind of different worlds that you mentioned, which was speed versus kind of quality, for founders again that listen that are in their first three years, say, we have, you know, 700,000 that listen, um, How should they think? Is speed of execution everything? Or is build slow, but build right the right way at that stage?
A Do both. That fits what you've got to do, you know, and I'm like, I'm in the middle of building. So I, you know, I did the shop fight lasting thing, hyperscale, and I've, I've done the one to N a lot, right? Which is the, after your product market fit, everything breaks. And how do you put the pieces back together and, and build a company and an organization to get to, you know, I'll, you know, hundred x that. Um, I haven't done the zero to one in a while, so one of the things I've been doing for the last year is a zero to one again, and just prove I can go back to band class and, and play my instruments, and uh, one of the, I'm, I'm living this viscerally right now, which is that debate of like speed versus quality, the good decision is every month pick, you know, half the things that have to be polished, like they're, like the best things on the planet, and half of them don't have to be. You know, and that's, and that's where you actually get long-term momentum, which is polish the things that you want. You know, you know, your customers are going to go, holy shit. Like I just use this app, blah, blah, and it's does X, Y, Z like amazingly. And then the other stuff, like, you know, they're not probably going to talk to their friends a bit. Right. So for me, that's the thing of just like every month there's like half I'm doing, I'm going to rush it. And in half I'm not. So the …
AI assessment note: “Do both. That fits what you've got to do”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q see everywhere, all over social, you know, AI will create the rise of, you know, billion dollar companies with one person. Whatever we want to call is that, you know, headline grabber. I know it's a really shitty question, so forgive me for it, but how do you think about the future of code and the future of product when so much can be done now with such little teams?
A I absolutely love where we're at with, um, AI and coding because it brings me back to, you know, I told our band leader that we didn't need the band to do a musical. So I've seen this playbook happen, like, what was that, like, thirty-some years ago, where I fired the band to do some music, and I've seen the power of, like, the computer's your, your, it's your co-pilot for doing things, right? And I, um, right now, I, I literally feel that giddy and excited about programming, because I've got a co-pilot in my IDE, and, and I think it'd be crazy not to use those tools, right? Like, there's no musician now to not have a computer in the music studio. Like it doesn't exist, right? Like, so I think we're just catching up now with a bunch of other trades where it's going to help us. And the way it helps me personally is, you know, it writes 80% of my code. It doesn't write my architecture, but it, it, The, the programming AI tools now let me work on the hard stuff, which is, which is phenomenal. And that's going to keep going. And you know, what's going to happen is we have a lot more software to write. And that's what people don't realize. Like, is there jobs in software development? Holy shit. Like healthcare, um, agriculture, uh, et cetera, like educate, like all these places that need technology have been completely under invested. We've got to distribute our programmers more tha…
AI assessment note: “what's going to happen is we have a lot more software to write.”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q What's been the hardest thing about zero to one with the new company? You know, I think it's so, maybe you'll tell me I'm wrong, but I think it's so different, you know, moving from the, uh, you know, scale that you were at with Atlassian and Shopify to zero to one. It's a completely different game. What was the hardest or most surprising element about that transition?
A I think that a lot of it's the same. I think the hardest part was it's, it is a bit more lonely, and for a long time, like, there's not a, like, there's two of us, and we're grinding and grinding, and, um, I think I, you know, there's a lot of friends at Shopify, and people I could shoot the shit with, and people who were in the same bucket, and I felt it was a bit lonely, and it was a year grind that, if you see some of my tweets, I had, I had some pretty, pretty low lows and pretty high highs, and I forgot You know, huge respect for, you know, that first year or so when you're just, you're trying to pull the pieces together, you're trying to figure out what to build, what not to build, and.
AI assessment note: “I think the hardest part was it's, it is a bit more lonely”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q fluff. And it makes me think to one of your tweets, which I loved. You said, I've retired from software process, no scrum, DDs, TDD standups, a load of other things. Instead, we just build and run software together. Software teams are built on process, as you know. Why is that wrong? Why are you issuing that? Can you just talk to me about why you don't need it now?
A Yeah. And as you can tell, as we're talking, I'm, I'm probably overly maniacal about, um, waste, maybe put it that way. Right. Um, and you know, I think that I've been pulled into the whole, there's a process that's going to make me better. Right, like there's, there's a thing there, like there's a way I should be working that's going to be better, that's going to bring something out of me, and what I realized a lot of, you know, and, and a lot of this came out of like some of the last years at Shopify, you know, as I was, you know, programming the organization and trying to get the most out of people is, is, um, we put process in play, like you put process in place because you got people and, and, and some of it's there, but I, what I realized is, is At the end of the day, what just really mattered was like a couple of people making some really good decisions and, and that's writing code and, and, and getting like, it's almost like your architecture is your strategy. So I was like, why don't we spend more time talking about that versus who's doing what? And are we have, do we have story points? And, um, like one really, really good example is I, I believe that one of the things that slows teams down the most is what I call time horizon friction, right? So we, so if you think about slowing down, it's physics, right? Like there's some friction in place that's going to slow you d…
AI assessment note: “what just really mattered was like a couple of people making some really good decisions”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q you is then, if we think about, you know, these brilliantly talented people who want to give us these updates, You got to get them in the door first. You've hired unbelievable teams. You know, Harley and Scott told me about your hiring abilities and scaling teams. How do you structure the hiring process and what are the stages for you? Cause it's really hard to know and do man.
A Hiring is really hard. Um, it's really hard. So I, I just kind of like a three step process. Oh, I'm not the process guy. Three things I think are important. The first thing is I call it the snowboard test, which is, uh, its premise around the snowboard test is I can't get another human to do something they don't really naturally want to do, right? So I'm like, just generally, like with my kids and my dog and cat, like if they don't want to do something, like it's not going to happen. So the snowboard test is, um, it's the way that you find out if someone is a left is goofy or not goofy on a snowboard, right? So goofy, depending on what foot you put forward. So the snowboard test is you push someone from behind without them noticing, and you look at what foot they put forward. That's their natural instinct, right? So I'm always thinking about it in an interview process. I'm like, how do I give you a A snowboard test where it's completely unbiased, but I learned the most about what drives you, you know, like, so, so one question for that would be, I was like, listen, I'm, I'm interviewing, you know, some exec role or something or someone senior. And I'm like, listen, you know, their question would be, you know, tell me about the job. I'm like, listen, let's not get into that right away. I'm like, you kind of know what, what we do as a company. I've, I assume you've done a bit of…
AI assessment note: “I just kind of like a three step process. Oh, I'm not the process guy.”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q Why, why, why, just before we go into that, why does it happen when you're rushed? Because you skip parts of the process.
A I skip. I, I don't, I don't do my three steps properly all the time. I get rushed. Right. And, and for me, like to get to know someone, like it takes a while, especially on that. Like when I talk about the snowboard test, like it's not one chat, it's a couple. And then I, like, I do really want to dig that it's it's I I'll, I'll skip it. And I like, ah, I saw that. So what I do to not rush hiring now is when someone leaves, I try to take the monkey off my back. And I, I always felt a huge amount of responsibility that when someone left on my team, especially a manager that was like, I told their team, I've got it. Don't worry. I'll hire someone new. You know, they were always like, there's always a bit of unknowns and people don't like that. And at some point, either it's because I got older, I didn't give a shit, or I just was in so much pain that I, I remember sitting a team in a room once and their, their manager had left their VP, whatever. And I was like, you guys are all adults. You all are doing great work. Keep it up. What can I do to help? I have no idea if it's going to take me one week or six months to hire replacement, but what are we shipping the next six months that I can help with? And, and everyone put their hand, like everyone got super pumped about it. I just brought it back to like, what are we, what are we here for again? Right? Like you guys, like you guys …
AI assessment note: “I don't do my three steps properly all the time. I get rushed.”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q What's been the hardest thing about zero to one with the new company? You know, I think it's so, maybe you'll tell me I'm wrong, but I think it's so different, you know, moving from the, uh, you know, scale that you were at with Atlassian and Shopify to zero to one. It's a completely different game. What was the hardest or most surprising element about that transition?
A I think that a lot of it's the same. I think the hardest part was it's, it is a bit more lonely, and for a long time, like, there's not a, like, there's two of us, and we're grinding and grinding, and, um, I think I, you know, there's a lot of friends at Shopify, and people I could shoot the shit with, and people who were in the same bucket, and I felt it was a bit lonely, and it was a year grind that, if you see some of my tweets, I had, I had some pretty, pretty low lows and pretty high highs, and I forgot You know, huge respect for, you know, that first year or so when you're just, you're trying to pull the pieces together, you're trying to figure out what to build, what not to build, and.
AI assessment note: “I think the hardest part was it's, it is a bit more lonely”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q Why, why, why, just before we go into that, why does it happen when you're rushed? Because you skip parts of the process.
A I skip. I, I don't, I don't do my three steps properly all the time. I get rushed. Right. And, and for me, like to get to know someone, like it takes a while, especially on that. Like when I talk about the snowboard test, like it's not one chat, it's a couple. And then I, like, I do really want to dig that it's it's I I'll, I'll skip it. And I like, ah, I saw that. So what I do to not rush hiring now is when someone leaves, I try to take the monkey off my back. And I, I always felt a huge amount of responsibility that when someone left on my team, especially a manager that was like, I told their team, I've got it. Don't worry. I'll hire someone new. You know, they were always like, there's always a bit of unknowns and people don't like that. And at some point, either it's because I got older, I didn't give a shit, or I just was in so much pain that I, I remember sitting a team in a room once and their, their manager had left their VP, whatever. And I was like, you guys are all adults. You all are doing great work. Keep it up. What can I do to help? I have no idea if it's going to take me one week or six months to hire replacement, but what are we shipping the next six months that I can help with? And, and everyone put their hand, like everyone got super pumped about it. I just brought it back to like, what are we, what are we here for again? Right? Like you guys, like you guys …
AI assessment note: “I don't do my three steps properly all the time. I get rushed.”
Answered raw tape
D 4 · C 4 · P 4 · Cm 4 4.00
Q see everywhere, all over social, you know, AI will create the rise of, you know, billion dollar companies with one person. Whatever we want to call is that, you know, headline grabber. I know it's a really shitty question, so forgive me for it, but how do you think about the future of code and the future of product when so much can be done now with such little teams?
A I absolutely love where we're at with, um, AI and coding because it brings me back to, you know, I told our band leader that we didn't need the band to do a musical. So I've seen this playbook happen, like, what was that, like, thirty-some years ago, where I fired the band to do some music, and I've seen the power of, like, the computer's your, your, it's your co-pilot for doing things, right? And I, um, right now, I, I literally feel that giddy and excited about programming, because I've got a co-pilot in my IDE, and, and I think it'd be crazy not to use those tools, right? Like, there's no musician now to not have a computer in the music studio. Like it doesn't exist, right? Like, so I think we're just catching up now with a bunch of other trades where it's going to help us. And the way it helps me personally is, you know, it writes 80% of my code. It doesn't write my architecture, but it, it, The, the programming AI tools now let me work on the hard stuff, which is, which is phenomenal. And that's going to keep going. And you know, what's going to happen is we have a lot more software to write. And that's what people don't realize. Like, is there jobs in software development? Holy shit. Like healthcare, um, agriculture, uh, et cetera, like educate, like all these places that need technology have been completely under invested. We've got to distribute our programmers more tha…
AI assessment note: “we have a lot more software to write. And that's what people don't realize.”
Answered raw tape
D 4 · C 4 · P 4 · Cm 4 4.00
Q So do you think teams get incredibly smaller? Do they just ship more ship faster? How does that change?
A Honestly, I love it. I think companies are going to unbloat and we're going to distribute programmers, right? Like there's, we've got a global, you know, lack of procreation happening. We're going to have less and less people who can, who can build technology where we need it. Like we need more efficiencies in agriculture and healthcare and education and renewable energy. Like, I think we're going to distribute these programmers that we're Making tweets boost on Twitter and Facebook, and we're going to distribute them more because we are going to need less. But I tell you, I think the pie is going to grow in terms of the kinds of problems we can throw technologists to. And I think that's, that's kind of what's going to happen.
AI assessment note: “I think companies are going to unbloat and we're going to distribute programmers”
Answered raw tape
D 5 · C 4 · P 3 · Cm 3 3.90
Q Why do you love that question so much? And what do the best answers elicit or show?
A Cause I want to know if someone's got a cool, like an internal quality bar, you know? So I'm going to like, and I'm on it again. I want to know what, like what they would put on their Life's trophy of what they're proud of, you know? And so it, it both gives me an idea of like their level of, um, difficulty, you know, because you've got this job and you're like, I think it's a difficulty, 9.5. And then they give you, oh, the hardest thing I did was X. I'm like, Ooh, that's a 7.2. I was like, okay, well, I think they can stretch, right? Like, are they gonna be able to stretch that? That's, that's cool. But, and then, and then, and then that leads you down a lot of things that are going, well, why do you think it was hard? Have you seen other people who are doing this? What do you, what do you like? It just, I just want to get to know someone about what they built, right? Again, about not how do you feel about how do you build it, right? And then, and then it was hard. How do you deal with that? How did you get help? Like there's so many twists and turns around just asking someone what they've built and, and, and how proud they are about it. So that's, that's usually the, the kind of the three questions. And then I, I, well, for someone senior, I'll, I'll have them have lunch with other folks. I think it's important that like, can they get other people to, you know, to, to Enjoy …
AI assessment note: “Cause I want to know if someone's got a cool, like an internal quality bar”
Answered raw tape
D 5 · C 4 · P 3 · Cm 3 3.90
Q Why do you love that question so much? And what do the best answers elicit or show?
A Cause I want to know if someone's got a cool, like an internal quality bar, you know? So I'm going to like, and I'm on it again. I want to know what, like what they would put on their Life's trophy of what they're proud of, you know? And so it, it both gives me an idea of like their level of, um, difficulty, you know, because you've got this job and you're like, I think it's a difficulty, 9.5. And then they give you, oh, the hardest thing I did was X. I'm like, Ooh, that's a 7.2. I was like, okay, well, I think they can stretch, right? Like, are they gonna be able to stretch that? That's, that's cool. But, and then, and then, and then that leads you down a lot of things that are going, well, why do you think it was hard? Have you seen other people who are doing this? What do you, what do you like? It just, I just want to get to know someone about what they built, right? Again, about not how do you feel about how do you build it, right? And then, and then it was hard. How do you deal with that? How did you get help? Like there's so many twists and turns around just asking someone what they've built and, and, and how proud they are about it. So that's, that's usually the, the kind of the three questions. And then I, I, well, for someone senior, I'll, I'll have them have lunch with other folks. I think it's important that like, can they get other people to, you know, to, to Enjoy …
AI assessment note: “Cause I want to know if someone's got a cool, like an internal quality bar”
Answered raw tape
D 5 · C 4 · P 3 · Cm 3 3.90
Q What do you think are the biggest mistakes that founders make when you review those three steps and then you look at how founders hire for product and engineering today?
A Like they're in that order at the top one is a snowboard desk. Like, I don't know how many times I've done it. Like, you know, I'm on the interview panel. I'm like, my feedback is I don't think they want to do this job. Like they want, they maybe want the money or the prestige, but I don't think like deep down, They need, they're gonna do what we think you want them to do. Like, what do you mean? And I mean, it happens a lot, right? So I think the, like, the alignment on what people want in their life is, is a big one, because I think if you, and if you fake want it, like, it's, You get like a 70% real person, but not like full on. And I think the second one is, I think someone who doesn't have the depth because again, like, like I'm talking like you're, you're, we're building multi-billion dollar companies where everything's hard and it's like eating glass. Like it's, it's hard, right? That you need someone who, you know, has, has the, has like the, the ability to like see and address things that every layer Of your company, right? From, from the code to the emotions, and, and seeing that, like, you're basically hiring people who are, who are full stack debuggers of, of things, and I think, um, I think people don't interview, like, they're like, they're really, really good at, like, these two layers, or they're really, really good, and, and it's not that you have to be good at…
AI assessment note: “the alignment on what people want in their life is, is a big one”
Answered raw tape
D 4 · C 4 · P 4 · Cm 3 3.85
Q I'm sitting down. I'm like, I'm, I'm ready, I'm ready to like dive in here. So I, I totally agree and I totally get you. Is there anything you think that Toby has to do differently in the way that he's creating this structure compared to how you do it in the way that you're creating your structure?
A I think it's based on, on similar principles. What's really interesting is I think, I think Toby and I both understand that there's some sociologic Things in, not in the way, but that we're conditioned to, right? So just think about what it was like in school for you, right? When you were in school. You go, you're given an assignment, You take the assignment, and your job's to go away and get an A-plus on the assignment, right? And not only that, you're not even allowed to talk to, you can't even talk to people. You can't even, like, get help on that assignment. Like, it's crazy. So you've, we've got, like, 21 years indoctrinated in getting a homework assignment, going away, and coming back. And then we're like, we throw you into the workforce, and we're like, by the way, now your job is to cheat as much as you can. I'm gonna give you assignment, And you could cheat. You better cheat, right? You better be looking at shortcuts, trying to find other ways of doing it and, and, and cheating, right? And, um, I think, I think as we're building companies, it's getting people in the mode of like, these aren't homework assignments where you, you get it perfect and you go, wait, you've got to cheat, right? You've got to build prototypes. You've got to look at other people. You've got to get feedback. You've got to put it in the wild and see if it doesn't break right away. There's, there'…
AI assessment note: “I think it's based on, on similar principles.”
Answered raw tape
D 4 · C 4 · P 4 · Cm 3 3.85
Q you is then, if we think about, you know, these brilliantly talented people who want to give us these updates, You got to get them in the door first. You've hired unbelievable teams. You know, Harley and Scott told me about your hiring abilities and scaling teams. How do you structure the hiring process and what are the stages for you? Cause it's really hard to know and do man.
A Hiring is really hard. Um, it's really hard. So I, I just kind of like a three step process. Oh, I'm not the process guy. Three things I think are important. The first thing is I call it the snowboard test, which is, uh, its premise around the snowboard test is I can't get another human to do something they don't really naturally want to do, right? So I'm like, just generally, like with my kids and my dog and cat, like if they don't want to do something, like it's not going to happen. So the snowboard test is, um, it's the way that you find out if someone is a left is goofy or not goofy on a snowboard, right? So goofy, depending on what foot you put forward. So the snowboard test is you push someone from behind without them noticing, and you look at what foot they put forward. That's their natural instinct, right? So I'm always thinking about it in an interview process. I'm like, how do I give you a A snowboard test where it's completely unbiased, but I learned the most about what drives you, you know, like, so, so one question for that would be, I was like, listen, I'm, I'm interviewing, you know, some exec role or something or someone senior. And I'm like, listen, you know, their question would be, you know, tell me about the job. I'm like, listen, let's not get into that right away. I'm like, you kind of know what, what we do as a company. I've, I assume you've done a bit of…
AI assessment note: “Three things I think are important. The first thing is I call it the snowboard test”
Answered raw tape
D 4 · C 4 · P 3 · Cm 3 3.60
Q So do you think teams get incredibly smaller? Do they just ship more ship faster? How does that change?
A Honestly, I love it. I think companies are going to unbloat and we're going to distribute programmers, right? Like there's, we've got a global, you know, lack of procreation happening. We're going to have less and less people who can, who can build technology where we need it. Like we need more efficiencies in agriculture and healthcare and education and renewable energy. Like, I think we're going to distribute these programmers that we're Making tweets boost on Twitter and Facebook, and we're going to distribute them more because we are going to need less. But I tell you, I think the pie is going to grow in terms of the kinds of problems we can throw technologists to. And I think that's, that's kind of what's going to happen.
AI assessment note: “I think companies are going to unbloat and we're going to distribute programmers”
Answered raw tape
D 4 · C 4 · P 3 · Cm 3 3.60
Q With less process, people monitoring becomes difficult. You hire someone and you don't know the first three months you're getting to know each other, but with less process, is it not harder to understand new team member quality?
A The only thing we should judge ourselves by is, is that output that people are going to see, right? Like our customers never see the sausage factory of how many meetings we have and what process we use. They're only going to see the output. So let's evaluate ourself on, on how good we see the output. And you know, one of the things that I, you know, when I do performance review for, for executives and managers that work for me, like the first question I ask is cool. What did your team ship and can you just rank For me, uh, what was good versus what was great, and I just, I want their opinion, right? And for me, that, that's a really good way. Like, I need everyone in the company to, like, Understand what we're shipping. How do you, how do we build some shared understanding of what great is and what good is? And, um, I want to see an organization where we have the most amount of people possible asking themselves that question. And what's great is there's no, there's no perfect answer of like, like I'm, I'm waiting to make sure I was like, but I, I need someone who has that, that, like you need everyone in the company who has that internal barometer of like looking at things that we're shipping and going like, how would I know if that was great? Like, how would I know if that email I sent to the customer was great? Like you should know that, right? You should be, so when you're w…
AI assessment note: “The only thing we should judge ourselves by is, is that output that people are going”
Answered raw tape
D 4 · C 4 · P 3 · Cm 3 3.60
Q With less process, people monitoring becomes difficult. You hire someone and you don't know the first three months you're getting to know each other, but with less process, is it not harder to understand new team member quality?
A The only thing we should judge ourselves by is, is that output that people are going to see, right? Like our customers never see the sausage factory of how many meetings we have and what process we use. They're only going to see the output. So let's evaluate ourself on, on how good we see the output. And you know, one of the things that I, you know, when I do performance review for, for executives and managers that work for me, like the first question I ask is cool. What did your team ship and can you just rank For me, uh, what was good versus what was great, and I just, I want their opinion, right? And for me, that, that's a really good way. Like, I need everyone in the company to, like, Understand what we're shipping. How do you, how do we build some shared understanding of what great is and what good is? And, um, I want to see an organization where we have the most amount of people possible asking themselves that question. And what's great is there's no, there's no perfect answer of like, like I'm, I'm waiting to make sure I was like, but I, I need someone who has that, that, like you need everyone in the company who has that internal barometer of like looking at things that we're shipping and going like, how would I know if that was great? Like, how would I know if that email I sent to the customer was great? Like you should know that, right? You should be, so when you're w…
AI assessment note: “The only thing we should judge ourselves by is, is that output that people are going to see”