Why Process is Killing Your Product Team and How to Remove it

with me,

good word. 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 I’ll tell you why. So I got into computer y things through, fine arts in high school. So we’re going back to 1988. I’m in high school, and I there’s just too many things I like doing. So I picked, I’m gonna 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 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 Mis Arabes 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 basically fired the high school band. I didn’t have to do anything for the whole musical that year, And I pulled off a Les Mis fan of the opera medley with my computer and my keyboard, and I I recorded as you know, I recorded a bunch of tracks. I did, you know, some stuff, and then I did one I played one live.

I was in grade 11 or something. I’m in grade 13 and I’m like, what am I gonna do with my life? And my guidance counselor was like, I think you should go into this computer thing. I’m like, oh, but my parents like, I know no one who does this for a career. Like, I’m probably just doing this for fun and she was right. I went into computer science and never looked back. So I think I I stumbled into it kind of young, but I I have I’ve always seen computers as a tool.

You know, for me, was like, hey, it’s really cool that I could do this thing. Like, computers like a a companion, a copilot for creativity, you know. I was not like a programmer. I was like a computer is like a tool that can make really cool shit happen. Right? And so that’s how I I fell in love with it.

listening to you

People always say, do something you love, and I’m like, do something you’re good at. In You some ways, my guidance counselor was like, hey. It looks like you’re good at it. There’s kinda no wrong path if you keep doing something you’re good at, and it turned out I was You were very good at it, and it

Yeah. It’s a good question. So from band class to leading and growing kind of the engineering orgs at these two companies that at the time had no idea where they’re they’re gonna be so massive. 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 nonoverlap of both. So the overlap is founders playing a long game and good at marketing. And that might be a bit weird coming from an engineering dude, but, like, founders playing a long game.

So making these decisions that, you know, I guess staying alive long enough that you just you’ll be around longer. And they’re both brilliant at marketing. Right? Harley, Mike, and Scott, like, they they knew the value of of getting eyeballs. And as an engineer building things, I’d I was at the time when I when I met all these folks, 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, something I learned from both.

strategically, both invested in in building communities around their company. Right? Like, you don’t you don’t build a product, you build a movement. Atlassian built a movement around open source twenty years ago, around easy software, and getting people really excited about it. Right? They did things like cash for clunkers. They’re going after Joel Spolsky at the time. It just built a movement around, like, how people work. Right? Their vision was, you know, empower, you know, everyone working on teams. Right? They built a movement around that. Shopify, same thing.

What did Shopify do? They I think at the time Harley and Toby got in touch with Tim Ferriss. Like, hey. You wrote a book at the four hour work week. That’s there’s a movement around being an entrepreneur. Shopify wasn’t about the product. It was about a movement of, like, let’s build this thing around entrepreneurship. And it’s not like that was, you know, accidental. I’ve got we had meetings about, you know, we have to create a a movement around entrepreneurship, and it turns out we have one product for that now.

We might have multiple in the future, but that’s what we wanna do. And both those companies did that really, really well. I learned so much because as an engineer, again, as a product person, the most important thing to do is get a group of people together that care about what you care about as much. And I think most companies have done that amazingly.

I’m curious. What do you think? What do you you know both. You’ve interviewed both. Let let’s compare notes. What do you where do you think they don’t overlap? Am I allowed to do that? Can I ask you questions? You can, but I’m just

Yeah. And I think I think one one thing you’re not seeing is is there’s pairs of people. Right? There’s Harley and Toby, and then there’s Scott and Mike. Right? So all these companies have a bunch of really good people who are who are making decisions. And I think the non overlapping I saw the most from from the inside was Shopify will ship on quality. Atlassian will ship on speed. And I think that’s culturally, like, Atlassian does a lot of stuff. You go to their web page and there’s a lot of products, they’ve a lot of m and a.

There’s a lot. Right? There there’s a lot and I think that was driven culturally. I think the founders are very they’re good at acquiring, turning that into monetization, and using their, yeah, using their pool of customers really well. Both turned into really great companies. At Shopify, we spend a lot more time on doing less things. And then from the outside, you might say, well, we did a lot, but less things and we would and especially Toby would would stop things based on quality, which why I would not see as much at Atlassian.

Now both companies, you know, obviously evolved since then, have done a lot of things, but you can still see that in yeah. I I think Atlassian was a crazy good business in terms of, like, as you said, Scott’s really good at at at numbers. I remember seeing spreadsheets of spreadsheets of here’s what, you know, Atlassian is gonna look like in 2020 and 2010. Really good mechanics of how how to create big great businesses. Right? And and Shopify, think, great business. I think the product is really, really good.

I think that we didn’t extract as much business, right, from it. Like like Shopify could be 10 x the revenue. Right? If you look at how much value is being provided. So very different companies. Now both are really successful, and you could go in the past and go, actually, if you did that thing, that would like there’s some magic sauce that made Shopify what it is today that if you would have done some more pricing optimization, maybe it wouldn’t turn into it, and the same thing for Atlassian.

Right? But that’s where the Venn diagrams don’t overlap as much.

Let’s just get into the comparison to, like, Atlassian and Shopify. Think Atlassian was a lot better extracting value, like revenue from that value that you’re giving. That’s what a company does. Was like, I’m gonna give you some value, and I’m gonna over time extract some revenue so I can keep giving you value over time. Right? You have to create a feedback loop there and Atlassian did a better job, I think, monetizing some of the products. Shopify is starting to do it. Right? Raised prices for Plus recently and I think it’s something we talked about internally.

And and the other thing, when you’re building a company here’s the other thing to realize. When you build a company, you have one thing to do. It’s like build a product that people can use and they love it and they tell their friends about it. If you do that for ten years and you figure out how to monetize it over time, like, that’s an okay position to be in. Right? Monetize enough to keep going, but you have some flexibility in how are you gonna do those levers.

So which means that if you spend too much time looking at the spreadsheets, you’re gonna forget you’re gonna forget about your priority number one, which is you have to get people to love your product and tell their friends about it, and then actually, like, yell to their friends about it, which I think both companies have done have done really well. And then the way you monetize that, if it’s a long game, maybe the first ten years, you break even, you’re making some profit, and you you’ve got some levers to play.

Right? And I think both companies use those levers differently. Both have been extremely successful, but it’s really interesting to see kinda two different playbooks.

people love it more? I think in your in your first couple of years, absolutely. Companies are gonna die from indigestion before they die of starvation, which means that we all have way too many ideas in our brain, and our instinct is to give everyone everything, and it’s really hard to say no. So you’re absolutely true. Right? Give people a couple of things that are really, really good, and then buy you time to figure out what the next things are. If we think about the

way at that stage? Do both. Like, I’m in the middle of the building. So I I did the Shopify Atlassian thing, hyperscale, and I’ve I’ve done the one to n a lot. After your product market fit, everything breaks. And how do you put the pieces back together and build a company and an organization to get to, you know, 100 x that? I haven’t done the zero to one in a while. One of the things I’ve been doing for the last year is a zero to one again, just prove I can go back to band class and and play my instruments.

And I’m living this viscerally right now, which is that debate of, like, speed versus quality. The good decision is every month, pick half the things that have to be polished like the best things on the planet, and half of them don’t have to be. And that’s where you actually get long term momentum, which is polish the things that you want. You know your customers are gonna go, holy shit. I just use this app blah blah, it’s does x y zed, like, amazingly. And then the other stuff, like, you know, they’re not probably gonna 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 gonna rush it, and then half I’m not. The question to you and these founders then is, like, what’s in each bucket? Not pick one bucket. Like, that’d be stupid. But what’s in each bucket? How do you know that every month? And how do you readjust that every month? Are there things that should

Yes. Absolutely. So I’d say, like, for me in my in my current startup, I was like, I’d love to build a multimillion dollar business with the least amount of people possible. So I was like, how do I do that? There’s obviously some technical foundations we have to put in place so that, you know, I’m not woken up at night or I I don’t have to hire a bunch of people, like, so we I did spend a bit of time getting some of that in place, obviously.

And then I’d say the designers we work with, like, I’ve got this designer who’s really good, I think they’re honestly, it’s a weekly debate on what we do now. But I think one of the ways you get speed and quality is by time capping things and then deciding as a team, again, what has to be polished, what doesn’t have to be. And I think it’s thrown my team for a loop a bit, which is I just don’t wanna talk about that much. That doesn’t matter, and no one does that.

Everyone everyone’s way too polite. Everyone’s wants to talk about stuff that’s gonna happen in the future. I’m like, either it’s shipping this week or we’re gonna discuss a direction of something that we, you know, we have to exchange some ideas, but it’s time capped. And I think that’s given us a huge amount of speed, but it’s been very culturally jarring for people. How do you measure

I just look at code too. How much do we ship? Code talks and bullshit walks, which is I see where we’re shipping. Is it good? You see, we ship this stuff this week. And it’s not are we doing more than last week? It’s like we have a consistent of we this kind of stuff, right, every week. And it ebbs and flows, but over time, I’m like, if we can keep that cadence up, I’m I’m kinda happy. Right? And I literally just look at the PRs and the code that we ship and how much time we spend on that.

That’s literally all the progress. And I that’s the exact same measure I had at Shopify, by the way. It’s not different. There’s no magic thing. I’m like I was like, what are we shipping? And and then you have to look at there’s there’s things that you ship that are different. Right? There’s some things that are one line of code. There’s there could be some magic in one line of code. So it’s not necessarily, like, number of lines of code, but it’s just you see this velocity happening in things shipping and you just you you get there’s this, like, humming in a company of shipping.

When you see that happening and it’s not a of meeting. It’s it’s not a of we’re talking about stuff, but it’s, like, after all that filtering, if you discuss, you align is, can you keep shipping stuff? For me, it’s like the ultimate measure. It’s a very

Yeah. And as as you can tell as we’re talking, I’m I’m probably overly maniacal about waste, maybe put it that way. And I’ve been pulled into the whole, there’s a process that’s gonna make me better. There’s a way I should be working that’s gonna be better, that’s gonna bring something out of me. And a lot of this came out of, like, some of the last years at Shopify, you know, as I was programming the organization and trying to get the most out of people is 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 us writing code and and and getting 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 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.

So if you think about slowing down, it’s physics. Right? Like, there’s some friction in place that’s gonna slow you down. So I call it time horizon friction. Time horizon friction is caused by a lot of process. And that process is you have a lot of people who want to put plans in place, and and and they feel comfort. You you talked about how do you get comfort in progress is some people get comfort in planning progress. They go, man, we’re freaking nailing it. Like, we’ve got plans for these 10 things, and we’re got I’ve got a good road map.

You know, I’ve got people that are really excited about what we’re building next. I I was realizing, like, I was, like, Shopify is slowing down in these places. And then you I do an audit of, like, of things. And we’re like, we’ve got, you know, we have planning process. We have we have to write briefs. We’ve gotta get road maps aligned. And I was like, holy shit. And you know what happens then is you end up having more meetings about work that you’re not doing yet than you are doing the actual work.

So so I call it time horizon friction because you’re planning the future and you’re not building the present. And think about an organization, and and I’m sure people listening, you’ve all lived this, is you have a lot of people who can’t write code in a company, but they’re gonna see progress as having plans. So they’re gonna have plans, but the only way to have plans is you have to talk to people writing code. Because you’re gonna put a plan together, you go, can we do this?

How long is it gonna take? So you end up having meetings with people doing the planning to help you do the planning with the people who are doing the building. You see that. So you end up having this bottleneck of way too much planning happening for the actual output of building, and you can’t plan without the builders. So at some point, I was like, what if we just cut out this planning process has to be completely thrown out. And I bet most companies completely, like, over plan a 100 x.

I’m not saying you don’t plan. I’m saying you should just plan enough. I’m swinging the pendulum personally now because I believe there’s a model of progress and shipping things that you can take a lot of cruft out. And I’m in this experiment now of taking as much cruft as I can out and building and time capping, and I’m absolutely loving it. I’ve never felt as productive. I feel like we’re getting so much shit done, and and that’s why I tweeted. What does yours look like today then?

Just build in silence on your own and ship. No. No. It’s super easy. It’s like, we just said, where do we wanna be in three years? You need a chat about that. Like like, what are we about? Okay. What are we what are we about? What are we not about? Cool. We realign it every quarter, whatever. Like, cool. And then we’re like, what are we doing next and next month? Cool. So I literally I go into linear. I we write we have a meeting. Right? What are we doing next next month?

It’s cool. And we have one a one hour meeting a week on who’s stuck. That’s it. That’s literally all we do. And we ship. And and you write code. Like, you just you write your product. We ship it. We run builds, like, all the other shit. Like but you’d be surprised at the like, it makes everyone on my team very uncomfortable. We’ve all been, I think, indoctrinated into planning reduces risk, and I think shipping reduces risk. So as a company, your job is to reduce the most risk possible, and I just really believe shipping does that.

I believe Toby at Shopify is implementing this exact same thing. I think we’re doing it in parallel universes, we will have beer every summer and compare notes. But I I I just trying to believe that some of the shift that Toby and and Harley have been making at at Shopify are to get towards this. Now, I’m not saying align alignment’s not important. You have to be aligned. Like, a a 1% difference in trajectory between the earth and the sun, 1% puts you 1,200,000 miles away from the sun.

So people can drift and teams can drift. So the question is, how do you align? There’s a million ways of doing that that are very ineffective and some ways that are way more effective at aligning.

I think it’s based on similar principles. What’s really interesting is I think I think Toby and I both understand that there’s some sociologic things, not in the way, but that we’re conditioned to. Right? So just think about what it was like in school for you. 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. 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, twenty one years indoctrinated in getting a homework assignment, going away, and coming back. Then And 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 I 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 away.

You’ve gotta cheat. Right? You’ve gotta build prototypes. You gotta look at other people. You gotta get feedback. You’ve gotta put it in the wild and see if it doesn’t break right away. There’s there’s, like, so many things that we’ve gotta do when we actually build things in the real world and real companies that we’ve gotta unprogram from all these people who are in school doing homework assignments and trying to get an a plus and not cheating. So, you know, that’s something that we’ve gotta really almost beat out of people in our education system to get people to actually build things.

And especially, like, you know, technically and engineering and product, it’s just like that that rhythm of building things, I I think, is is different. And that’s why I’m I think swinging the pendulum here is is really interesting and just get kids to, like, let’s write the code. Let’s build it. How do you know it’s gonna work? And and and I think we’re gonna get velocity out of doing that versus just talking about things.

I think it’s easier. You know, the only thing we should judge ourselves by is is that output that people are gonna see. Right? Like, our customers never see the sausage factory of how many meetings we have and what process we use. They’re only gonna see the output. So let’s evaluate ourself on how good we see the output. And when I do performance review for for executives and managers that work for me, like, first question I ask is, cool. What did your team ship? Can you just rank for me what was good versus what was great?

I want their opinion. That’s a really good way. Like, 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? Wanna see an organization where we have the most amount of people possible asking themselves that question. 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 so when you’re writing it, then and you should be building it and getting better all the time. And I think if you build an org organization where you don’t reward yourself by what process you use, but you reward yourself by a shared understanding of what great looks like and and building towards that, I think that’s I think that’s how you get better.

The context here is everyone’s heard of that phrase. It must be written in, like, a bazillion Harvard management books. Right? Like, hire great people and get out of way. You know? Like and I believed it. I was like, holy shit. Like, that makes so much sense. Right? Because everyone’s love loves autonomy. Just give people autonomy. And when 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. Like, there’s no way you do that by letting people go in their own direction.

Right? Like the Steve Jobs analogy, there’s a rock tumbler that you’re gonna be in together to figure out how you’re gonna polish things, how you get a shared alignment. So so for me, you know, hiring great people and get out the way is, like, assuming that everyone is magically gonna have the same understanding of the world, is magically gonna have the same quality bar, is magically gonna be aligned on how they do things, like, is impossible to happen. Right? So 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 and my thesis here is why it’s it’s it’s absolutely terrible is and and why I’m very strongly saying that is because I think people believe it’s really good. And the second thing is the only way you get you get that level of autonomy is when you actually align a lot of things together. So I’ll give you a really concrete example. When I would onboard new VPs that would work for me, I would very clearly say, and this is I’m not smart. I just I learned this over many, many years is I would go, listen.

We’re gonna spend a lot of time together. We’re gonna spend time together like we were pair programming, like we used to do when we were programming all day. We’re gonna pair program on leadership. And the reason we’re gonna pair program is it is as complex as programming. Like, there’s typos, there’s bugs, it’s it’s hard. And the only way we can get to know each other is we’re gonna have to pair program on leadership. And the way we do that is there’s a couple of things that I’ve I’ve noticed in the org that I really want you to ship.

There’s three things in the next six months that listen. I’m gonna make it easy. There’s you don’t have to find these. There’s three things we have to ship that I’d like you to to lead. And I’d like you, during that time, I’d like you to find three other things that we should do that are really important. And then what’s really cool is we’re like, I’m not going, here’s exactly all the things you’re gonna do for next year. I’m just I’m I’m helping the the kind of the onboarding.

I’m like, let’s get let’s get aligned on on how you ship things. So I’d go, for example, like, really great guy, his name’s Farhan. I think he runs engineering at Shopify now. I hired Farhan. He’s almost too smart. He knows he’s looking at everything and I’m like I’m like, dude, Farhan, I know you have all these ideas. Here’s three things we’re gonna do. We have to become we wanna become the best company for React Native on the planet. We’re making a bet on React Native, and I need you to publish a blog post and do some research on what we’re doing internally in React Native.

I’d love you to lead the mobile team to get us reoriented around React Native and come up with we’re redoing POS, blah blah blah. Cool. Those three things. And then cool. I’m like, can I review your blog post? And then we probably went back and forth on it five, six times together. And I was like, cool. I was like, hey. I’d say that differently. Why? Oh, that’s super interesting. We got to know each other in this super fun way of just shipping stuff together. Right? Instead of talking about it, I was like, can you write that thing?

Let’s let’s oh, I I I hadn’t thought about doing it that way. That’s really smart. That’s cool. I learned something from Farquhar. Then the flip side, he’s like, oh, Jean Michel, I didn’t see things that way. Right? So we got into this, like, pairing mode of really getting to know each other. And then by year two and three, I’m like, Farquhar, what do you wanna work out? We kinda know each other at that point. Right? But that’s very different onboarding and very different philosophy than I think a lot of companies.

They feel that any any premise of command and control is like is is like a a religious faux pas now. Right? Like, if you if you don’t, like, pray to the autonomy pulpit and church, you’re almost burnt at the stake these days. Right? Like, what do mean autonomy? Everyone wants autonomy. I I swing the pendulum. I think that you’ve gotta have a lot of high alignment, and I don’t you don’t do alignment by meetings necessarily. Like, alignment’s not this. We have to talk all the time.

Alignment is like sending your boss a Slack message every day going, hey. Here’s two decisions that I saw. I did a b c. What do you think? Bam. Okay. Cool. That’s cool. Let’s let’s align on decisions. Let’s align on what did you see and what do I think? Like like that, you can do these micro alignments all the time that are that are really amazing, you know, to the point where we would hire new executives at Shopify or Atlassian. And one of the questions I’d asked after, you know, this new CFO or the c new CMO had been onboarded for three months, I’d go, hey.

How often do you talk to our CEO? And they’d go, well, we have our one on ones every week. I’m like, oh, wow. That’s not a lot. And they’d be like, do you mean to that a lot? I was like, well, I I do at least one Slack a day. And they’re like, what do you mean? Like, I don’t wanna bother them. And what do you mean? You mean bother the CEO? Like, was like, let me tell you something. The the only thing on the CEO’s mind right now is everyone running off in different directions and not be able to kind of understand what kind of decisions we’re making.

So I’m like, I share a decision every day with the CEO by Slack or by email, like, depending. And like, I’ll and I’m like, they don’t have to respond to me. I’m just doing these micro alignments of, hey. I saw this thing. What do you think? Or, hey. Do you see this demo? That’s cool. Or was like, hey. I need a hand hand with this. So I’m like, I’m such a fan of, like, these micro alignments that you’ve gotta build into your habits, and I feel that if you I’m honest one, Michelle.

I you know, I manage

It’s interesting. I think that the world is so complex. Why would I build a company where I can’t use everyone’s brain? It’s always the thing I’m thinking about. Right? So so it’s like, for me, I’m like, I have to tap into my boss’s brain in the the most effective way possible because that’d be stupid to not tap into everyone’s brain. So for me, I see it less as bothering, right, and more as as I need to tap someone’s brain. So

It has to be a bit more natural than that, and I think 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 medium size, and then leafs are they don’t matter.

Right? So, like, let’s talk about the roots together. Don’t surprise me. Right? Make sure that the trunks, if you wanna brainstorm, I’m always available for that. Like, I always wanna learn something from you, and maybe I can bring some input. And leafs, as you said, don’t bug me about that. Right? So 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 Tori, but it’s it’s simplistic. Right? Where I think building, you know, companies where there’s a lot going on, there’s a lot of micro decisions to be made that make a difference.

Like, sometimes, like, we’re gonna put the code there versus there. Sounds like, I just trust you versus that’s a root decision because that’s gonna lead on to a lot of other things. There’s no bad reason in getting a couple of, points of feedback. So that Susan Scott book and at Framework, I think is a great way to sit down with your team going, hey, there’s three types of decision we’re gonna be making. These ones, I care a lot about. These ones, I don’t versus I don’t care about them all, which is I think is gonna be a train wreck.

I’m just gonna blame my English isn’t my first language, so can I

it’s really hard to know and do. Man, hiring’s really hard. Three things I think are important. The first thing is, I call it the snowboard test, which is premise around the snowboard test is I can’t get another human to do something they don’t really naturally wanna do. Right? So I’m like, just generally, like, with my kids and my dog and cat, like, if they don’t wanna do something, like, it’s not gonna happen. So the snowboard test is it’s the way that you find out if someone is a left is goofy or not goofy on the 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 learn the most about what drives you? 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, tell me about the job. I’m like, listen. Let’s let’s not get into that right away. I’m like, you kinda know what what we do as a company. I I assume you’ve done a bit of research. I’ve got so many jobs jobs open. You could do anything here. What’s your dream job at Atlassian, at Shopify? What is it? Talk to me about why that is for ten minutes. Right? So so that question for me is like the ultimate snowboard test. I wanna know what people care about the most, like, viscerally care about because that’s when you’re not talking together, when you’re not with them, that’s exactly what they’re gonna do.

That’s step one, and you get to know and often, I’m hiring for x and I’m like, oh, shit. Their instincts are always on y. And then you have a decision. You’re like, well, can they do x and you need y or just like, you’ll see that. And and, you know, typically, for example, I’ll see instincts on, I really care about the culture and, like, cool. I really care about the process. I really care about the people. I really care about the tech. I really I really wanna do this.

And and so that that first alignment that you have with whoever you’re interviewing, for me, that snowboard test is is great. It’s super over over ended, like, but it it works really well. Like, you get to know kind of visually what people wanna work on. So that’s step one. I’m gonna I’m gonna pep you with questions afterwards. I’m gonna let you go through these steps because this is too good. Step two. Okay. So step one is is you kinda know what their instincts are, what they really like to do.

Step two is I wanna know how are you gonna do x? So then I’m like I’m like, show me how you’ve done x in the past. So there I’m basically I want them to go into teacher mode to me, which is cool. You wanna do x? Can you entertain me and teach me something about x for the next hour? You know? So I’ll I’ll I’ll just geek out for an hour, like, talk about x. Like, oh, I’d love to, you know, build a system that could do this.

And then I’m like, cool. Like, how would you start? And how would have you done this before? What do you do? Like then I’m trying to figure out layers. Because I think I think great skills for any human is a deep appreciation of all the layers that come into problem solving. Right? So, like, if someone wants to be a great like, I’d love to build a team and I’m like, cool. Like, do you know psychology? Have you read any books on human motivation? Like, how do you do that?

Like, I wanna understand someone’s playbook in terms of what what depth they have in that area. I gave them the snowboard test. They told me they like it. Cool. Like, how much do you really like that? And I would I wanna know someone’s depth. And, again, there’s no right or wrong answer here. It’s just discovering, like, what some like, do you even like the conversation? Is it fun? Do you like, I hope after talking to someone about the thing that they really love that you come away with that come away out of that chat super energized and maybe learn one or two things.

Like, that’s great. I wanna work with people like that. Right? So that’s step two for me is is that kind of deep dive understanding depth. Go. Step three.

you’ve got writing on your hand.

Yeah. So, you know, step three then is is gonna be obviously, like, talking about, okay, well, here’s kinda what the job is. I’d like to understand how they’d how they’d approach that, what they’ve done in the past. I I love this one question, which is what’s the hardest thing you’ve built before? Why do you love that question so much? And what do the best answers elicit or show? Because I wanna know if someone’s got a, like, an internal quality bar. Again, I wanna know what, like, what they would put on their life’s trophy of what they’re proud of, you know?

And it both gives me an idea of, like, their level of 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, oh, 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 leaves 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 wanna get to know someone about what they built. Like, there’s so many twists and turns around just asking someone what they’ve built and and how proud they are about it. So that’s kind of the three questions. 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 Do you care if they’ve

no, it doesn’t matter? I’d say generally not. I think the those three step process for questioning is really about getting to know that human. 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 just throw into the deep end into into anything, and they’re gonna learn it.

Right? I want people who can grow quickly and people who can understand that problems are multilayered and see that and fix it. I think that’s more important. What do you think are

Like, they’re in that order. At the top end of the snowboard desk. Like, don’t I 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 wanna do this job. They maybe want the money or the prestige, but I don’t think, like, deep down, they’re gonna do what we think we you want them to do. Like, what do you mean? And it happens a lot. Right? So I think the, like, the alignment on what people want in their life 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, 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 has like the the ability to like see and address things at every layer of your company. Right? From from the code to the emotions and seeing that, like, you’re basically hiring people who are full stack debuggers of of things. And 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 all of them and there’s no perfect people. But actually, out of the interview process, knowing that, going, I just think they’re really good here versus there, like, versus people just getting so in love with, like, we spent three hours talking about this one layer of of things. Right? I’m like, yeah. But when you throw them in this thing, there’s other other things you’re gonna have to see. At least know that before you you say yes to the hiring process.

So for me, that those are kind of the two, two biggest mistakes I’ve seen. What’s

I’ve done it so often. Like, for me, it’s always when I’m rushed. It’s always when I’m rushed. I tell you what, you’re rushed a lot when companies are going gang gangbusters. Right? Or you have you’ve got pain. So I’ve so one of the things I’ve tried to do to remove the rush Before we go into that, why does it happen when you’re rushed? Because you skip parts of the process? Because you I 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, it takes a while. When I talk about the snowboard test, like, it’s not one Chad. It’s a couple. And then I like, I I do really wanna dig that. It’s it’s I’ll I’ll skip it. And I’m like, oh, shit. 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 gonna take me one week or six months to hire replacement, but what are we shipping in the next six months that I can help with? Like, everyone got super pumped about it. I just brought it back to, like, what are we what are we here for again. Right? You guys are all adults. Right? You can drink. You can vote. You have kids. All that shit. Like, what are we shipping together? And I’d always bring it back to customers. Like, what do our customers need from us right now?

It did not change. Yesterday, that person was there. Now they’re not there. Nothing nothing’s changed about what we have to ship. How can I help do that? Right? And they’ll go, oh, well, maybe we should do this and that. I was like, cool. Yes. No. That let’s do some stuff. Sounds good. And then I would also I go, listen. Let’s get ready that we might have not have someone in here for six months. So I took that stress off me. I’m like, I’ll take some of my time a bit.

The second thing that happened is everyone just steps up. They they get jazzed about what we’re doing. Right? They’re here. Like, they’re still getting jazzed about doing this, and they get they get jazzed about just I see their face light up when we start talking about what we’re what they’re shipping and what they’re working on. And, I think that connects me with them, gives me a bit of time, and then I think I make higher better at least personally, I make better hiring decisions when I get a bit of time to to get to know people better.

The right answer is buy yourself some time. One of the favorite books that I’ve I’ve read about leadership is, I think it’s called how to negotiate like your life depends on it. In the first chapter, I tell my kids about this because it it it taught me so much of just, you know, someone someone has your kid as a hostage. They want a million bucks and you’re on the phone with them. And the first thing you do is you’ve got a monkey on your back because the hostage negotiator says, I need a million bucks tomorrow.

And you’re like, you have all these things you can say. And then, like, the the the thing you should do is buy yourself some time. So you throw the question back and you go, how do I get a million bucks in a day? Like, that’s a lot. And then the hostage negotiator has to think about that. They’re like, oh, yeah. That’s a lot. Okay. I give you a week. Right? So that’s I just remember that’s the first example, which is buy yourself some time all the time.

Right? So so how do you buy yourself some time in a company as a as a manager, as an exec? I’m like, take some monkeys off your back and get some people involved. Like, you know, like, for me getting people in the room and going, hey. That VP is not here anymore. Cool. But we still have customers. Let’s keep going. It’s buying some time and get people let’s get refocused on on what we’re here to do. And that’s why buying time is important. Now this flip side of, hey.

We’ve got all these companies, and I’m sure as VCs and investors were like, you have to hire great talent. Absolutely. So the other thing that I thought was really important was, like, if I did not talk to a candidate every week, and I don’t even call them candidate. If I did not talk to someone that I’d love to work with every week as part of, like, my ongoing networking, I was not doing my job. Right? So I I had this buzz flow of, like, let’s just talk to interesting people all the time.

Like, I’d ping, you know, seat like, CTO of Microsoft. Like, hey, Kevin Scott. Like, I’d love to talk to you about some things that I’m, you know, like, cool. Let’s have a chat. Or I’d or I’d talk to some I’d see some really good blog posts. I’d talk to people. Right? So I think as as a leader, the like, there’s no hiring process where you just start it and stop it. It’s always always going. So I think a lot of the the CEOs that I work with in some of the smaller companies, I’m just always asking them, like, have you talked to one person a week that at some point you wanna you you wanna work with?

And then what happens if you do that one year, two years, three years, four years, you’ll realize that when it’s time, you’re just gonna know so many people that you wanna work with. That one is, like, it’s gonna be super amazing, and then you can start to figure out when you have time. You can look at your Rolodex, and you go, cool. Let me go back to talk to those three people and figure out where they’re at. And so you end up basically having an ongoing continuous networking of cool people that you wanna learn from, that you can hire from.

And then you buy yourself some time internally by just realizing, let’s just not negotiate against myself and not be rushed. And for me, those those two things have been have been magical. It’s interesting that we’re

I absolutely love where we’re at with AI and coding because it brings me back to 1988 when I I told our band leader that we didn’t need the band to do a musical. So I’ve seen this playbook happen thirty some years ago where I fired the band to do some music. I’ve seen the power of, the computer’s your your it’s your copilot for doing things. Right? And I right now, I I literally feel giddy and excited about programming, because I’ve got a copilot in my IDE.

And and I think it’d be crazy not to use those tools. Right? Like, there’s no musician now that does not have a computer in the music studio. I think we’re just catching up now with a bunch of other trades where it’s gonna help us. And 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 programming AI tools now let me work on the hard stuff, which is phenomenal, and that’s gonna keep going.

And, you know, what’s gonna 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, agriculture, etcetera. Like, educate like, all these places that need technology have been completely underinvested. We’ve got a distributor of programmers more than we have before, and I think AI is gonna make that completely more possible. And I’ve never been as excited about being a programmer and a developer. What’s been the single biggest game changer in the last two years for you writing code?

I think having the AI copilot that I talked to nonstop. It’s blown my mind.

It’s a good I’m not sure. Like, it’s kinda like music. Right? In the music studio, it would give me my tempo. I can do a lot of tweaking with sounds. I can invent new sounds, but I’ve got the tune in my head. That’s kinda where we’re we’re gonna be at with with computers. So do you think teams get incredibly smaller? Do they just ship more, ship faster? How does that change the structure? Are gonna I honestly, I love it. I I think companies are gonna unbloat, and we’re gonna distribute programmers.

We’ve got a global, you know, lack of procreation happening. We’re gonna have less and less people who can who can build technology where we need it. Like, we need more efficiencies in agriculture, in health care, in education, in renewable energy. Like, I think we’re gonna distribute these programmers that were making tweets boost on Twitter and Facebook, and we’re gonna distribute them more because we’re we are gonna need less. But I tell you, I think the pie is gonna grow in terms of the kinds of problems we can throw technologists to, to.

And I think that’s that’s kind of what’s gonna happen. I’m just freewheeling here, but I’m

I mean, is if you go back in the past, is there a time where there hasn’t been the five incumbents that scare the crap out of you?

Yeah. Yeah. Maybe. I’m this is where I think you and I spend time in different places. So I’m more I look at things more as opportunities to build new things, and I’ve never seen as many. Right? And I I always get frustrated. I go to every government’s website. Like, actually, you know what the coolest thing to build right now? And this is where maybe from a VC, we might be at a point where we’re actually building human infrastructure a lot more now. Right? Which maybe the VC model might be busted.

But you know what I need is a comp I need a country operating system. I bet you like, if someone could come up with a country operating system, it’s probably the next biggest multi planet what would be the richest company on the planet is a company operating system, which is how do you run a country right now? Like, do you run a country? Website, taxes, bot like, all that stuff. Like, we are being it’s crazy how much crap software and technology we have out there. So so for me, that’s opportunity.

You’re seeing how do we make money out of it. I kinda don’t care. I just think I want to make, you know, everything we touch better. Right? Better customer experience, better product experience. So if I look at an opportunity, I’d love a company to build a country operating system. Request for startups.

is, you know But it’s not. It’s it’s like, but but how do you think about that? Right? Like, we might be at a point where we need more infrastructure than ever. Like, we build we’ve been building startups and things here and there, but how do we, like, how do we do the rest? Right? Like, how do I electrify our roads? How do we do better intake system in hospitals, data sharing? I I see a lot of opportunity there. Well, I think that’s what you’re seeing with the

I think they are, like obviously, it’s hard to build a it’s like almost a platform company. You’re building a foundational layer of that thing. Right? The Internet, hospitals, etcetera. It’s actually a lot harder, and you’ve got two exits. Right? Someone’s gonna buy you because you’re gonna build the layer and they someone else wants it, or it’s gonna take you twenty years before you you scale. But for me, I see it derisked because I I do I’ve been on the buying side of being in a bigger company going, that small company really they push that platform in a cool little direction.

Let’s let’s acquire them. So I I see some there’s always two exits for platform cost companies that I think is is useful to think about, right, as you start looking at at at at risks. And it’s harder, but I think, don’t we that’s hard tech. We have to get better at doing harder things. So

Wow. That is such an interesting question. How do you how does every every team get pulled down and and not do to the best of their ability? I think the one of the hard things about teams and building companies is it’s really hard to pace yourself. You It’s kinda like where you’re running a marathon. You know? Like, I don’t know if you’ve done any half marathons. Like, there’s always a pace bunny.

for two a year and a half. Well, there you go. Okay. So you know all about the pace bunny. There’s it’s really hard to have a pace bunny for a company and a team. Right? I’m a big fan of Pace Bunny myself. I’m like, as a leader of a company, you should always be looking for your Pace Bunny. So looking at what other people are shipping, looking at velocity of other teams, and a lot of the people that I talk to where I’m like, I’m building my hiring pipeline or I’m learning something, I’m always going outside to, like, you know, CTO at Spotify.

I’m like, hey. Can you talk about how you do inferring this? And did you tell me about your last couple of incidents? What were they? You know, like, always trying to, like, pace myself. I’m like, and often, you know, I’d be really hard on myself and go, oh, actually, we’re all doing this shitty thing. And then sometimes, I’d be embarrassed going, oh my god. We can be so much better. So I think, a really good tool from for, I think, leaders is build a pace bunny process of some sort where you can talk to enough people where you build kind of an internal model of of what great looks like, and then you bring that to your team.

And then you can, obviously, making sure you’re surrounded by people who care about that.

I think that a lot of it’s the same. I think the hardest part was it is a bit more lonely. There’s two of us, and we’re grinding and grinding. And there’s a lot of friends at Shopify and people I could shoot the shit with and people who are in the same bucket, and I felt it was a bit lonely, and and it was a a year grind that you see some of my tweets, I had I had some pretty pretty low lows and pretty high highs, and I forgot a 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

My wife just pulls away. She’s my counselor and my cheerleader. Honestly, like, yeah, she you know, some people don’t bring their work to their their spouses, but, I do a lot, and she’s my life partner. And, honestly, she’s my biggest cheerleader. The fun part about building zero to one two is it did let me try out a lot of cool companies, new products now. That, you know, like, you you read about them on Twitter and you see but now I’m, like, actually, like, hey. Let me use you think that your new thing is really cool?

Let me use it. So I’ve met a lot of really good people by just I’m gonna use your product, and I’m gonna give you some feedback. And it’s been it’s been fun. Like, I’ll give you one example. One of the products that I’m really pumped about now is called equals.com. So get equals.com. They’re doing something that’s super subtle, but actually the more you use it, the more you see the value in it. It’s kinda like I’d never invest in this if I didn’t use it day in, day out.

And because I think there’s some innovation that comes out that’s not deep tech, but that’s changing how you use something completely. So get equals is basically taking the SQLers and the Excelers and giving them a shared data warehouse where they can work together. Zero investment. I’m not getting paid for this. I’m just I just love using new things. We’re like, holy shit. This changes how I work. I do know

But they’re building a hard product, and this is, you know, I think to your question, Harry, right, about you know, there’s some startups who are solving some really hard problems where it might take $50,000,000 to get a one o out. Right? And how do we build a VC culture where that’s

And that’s why you’re a much better investor than I am. I’m a happy customer, and I see how it changed my life, but I have no idea if this is a business or not.

And and you’re right. Like, customer acquisition is is hard. I think that’s something I learned from Shopify and Atlassian is it’s hard. So my my zero to one, the first thing I did is you know, my cofounders are YouTube celebrities, so I’m like, okay. I’ve got that I’ve got that part nailed, so I can go to market quickly. So What’s the price point as well? Because

Yeah. I think they’re they’re marketing it as a business tool. So pricing’s kind of you know, it’s not a $4.99 pricing. It’s a it’s it’s gonna be the day data layer for your company. And if you’re not willing to pay $49 a month to, like, see everything that’s happening in your company, like, you’re probably not the right tool. So they’re I think they’re positioning themselves as a pro tool. Right? Again, is there a pro tool market? I think there’s some really good pro tools. You talk about Adobe, write some pro tools that have been, been successful.

But

I think CEOs underestimate go to market a lot. I think you talked about that. Like, how are they gonna acquire customers, and are they gonna be able to create a movement around what they’re building? And I see CEOs think they can do it, but don’t realize the grind it’s gonna take over year over year. And I think they see the outcome of companies like Atlassian and Shopify who’ve been doing it for fifteen to twenty years and assume it just happens, but it’s it’s daily daily grind to get people to care about what you care about.

That’s there’s a saying, which I said, no one cares about what you’re building. Like, literally, no one gives a shit about it as much as you do. And how do you get people to give a shit about it?

they hire too quickly. As a result, they don’t know what the capacity of their team actually is on paper. So I always wait till things break a couple of times before I add people.

I started on the support team at Shopify, and that was the best thing that I’ve ever done. And it’s the only time I did it. I spent one month, and I said, if I can’t take customer phone calls for the product that I’m leading and I’m building, I should be fired. So, I thought that was one of the best things I’ve ever did. I learned so much about the product. I learned about the team. I learned about customers. I turned out to be an expert user of Shopify, and I would recommend that everyone starting a new jobs would literally start on the phones.

What function has the most tension with engineering? I think the function has the most tension is the design, product, and engineering, like that triad. Right? That tension there.

That’s so so you’ve got two companies. I think there’s some companies that are very sales driven where absolutely there’s some tension on around sales. I think there’s a whole hour podcast we can talk about engineering leaders and how to how to manage that. It’s not removed the tension, but how do you use attention for good and not for bad. Right? Because that’s useful. And you can talk to Harley about this, but one of the things he did well, he he encouraged is I took over sales at Shopify for a year to remove.

So I had 800 people, at Shopify that were in sales, and they reported to CTO for one year because we had a lot of attention, and we had to realign. We had to decide on, you know, what customers are saying yes to and no based on not just what we want money wise, but what we want product market fit wise. And it got me really involved in in in helping with that tension, actually accelerating it. Right? And one of the things that is, like, I love sales, which is which is, like, bring us the right customers at the right time.

And I think one of the biggest problems with misalignment of sales is sales bringing you the wrong customers at the wrong time. So if you can realign that, and then you’re like, well, what are the right customers at the right time? Cool. Let’s talk about that. And I think that’s that’s one of the things that I did for the one year when I was running sales. And Harley was nice enough to hand me the keys for a year and then take them back, but was really realigning on that.

And and, know, for us was deciding Shopify is gonna be the biggest hype platform on the planet. We wanna land all the celebrities. We wanna land the biggest, retailers that are having pain points. And we we kind of listed, you know, and then, you know, we went ahead and and built for that. We said, we don’t wanna land these kind of customers, and we went through and kinda redesigned, you know, who we wanna land, focused the road maps on on delighting the ones we wanna land this year.

Is it a bit of being everything

Absolutely. Okay. Let’s peek into Shopify’s product strategy. It was exactly that. Right? So if you take all the retailers on the planet, right, you organize them maybe as a a bit more like a triangle. Right? So there’s complexity and there’s volume. Okay? Actually, if 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 merchant are often low complexity. Oh, holy shit. They’ve got something in common. They’re low complexity.

What does low complexity for retail looks like? It’s low SKU count. 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 seventy, seventy thousand 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 don’t crash.

We’ve got highest volume. Go let’s go after Supreme. Like, Supreme, again, like, a fairly simple business, high volume. Let’s solve that. And I’m like I was like, hey. I think we have five years of revenue in this bucket where we’ve got really good product alignment. Why are you trying to go close like FTD Flowers that got the most complicated business on the planet that I’d love to get them? But if I can buy you some time by just getting the right customers at the right time, we have time to evolve the platform.

We have time to do that. So I think that was, for me, was the biggest way of it wasn’t even removing tension. Was just put at the right place. And that once we had that, I was like, why aren’t you bringing us more customers? You know? Then I can I can put the gas on the sales team and and and get up there where you’re in and go, I told you what our product market fit? I want them all on the planet yesterday, and then they get busy.

It was a pleasure. We waited too long, and again, sorry for the 20,000,000 directions, but I I hope it comes out good. So thanks, Harry.