{audio:0:00:06} Adrian, could you share your experience in jazz and your role as the artistic director in the Ottawa orchestra?

{audio:0:00:13} I’ve been a musician for a very long time, for many decades. Obviously, running something like that orchestra, there is a love of music there and wanting to entertain and so on. But I think the thing that might be of particular interest to your audience is that one of the reasons that I founded that group and I’ve run it for 15 years, and still run it today, is that it’s actually been, almost, a social experiment. It’s really been a way for me to take a lot of the ideas that I’ve written about and that I’ve applied in workplaces, in various organizations, and tried to use the orchestra as a testing ground for those kind of things.

{audio:0:00:58} I think one of the things that is most important there is just the way in which we collaborate. Most music ensembles, for example, typically rehearse on a regular basis. They might rehearse every week, every month or whatever it might be. We don’t do that. We do have a season of concerts that we do each year and perhaps some other performances too. But what we generally do is, when we have something that’s coming up, I schedule a couple of rehearsals, just before that show and we come together and we rehearse it and then we perform it. One of the things that we do is, we set a pretty high bar and people come prepared. They give their best, individually, but then also as a group, we have to come together. The technical challenges of the music are often pretty high and the music is often quite difficult. We set the bar pretty high and everyone rises to that. They way that we actually engage with each other, at the rehearsals, in order to figure out how we make it into a great performance, even given limited rehearsal and preparation time, that’s really the interesting part.

{audio:0:02:23} The other thing that is interesting is that, on stage, even though I’m the leader of the group, a lot of the people who are in the group, who have played in the group, over the years, have worked out that we try to foster a very collaborative environment on stage, as well. That’s something that the audience also sees. They see that collaboration going on and the way that we interact with one another and they find that fascinating too. That adds to the performance.

{audio:0:02:52} Do you think that limiting that preparation time actually drives more collaboration and more creativity?

{audio:0:03:00} Yes, I think it does. I think there are two important things. One is that being forced to make a decision, to make something just good enough, especially when we are talking about things that are artistic or creative, on the one extreme, is that it’s technically perfect. Every I is dotted and every T is crossed and it’s technically perfect, but it’s totally devoid of any passion and any creativity. The other side of it is that you have total chaos and it’s totally unprepared and people are really feeling the passion but it’s a bit of a mess. Trying to find that balance is a really interesting thing.

{audio:0:03:46} Often, we will be rehearsing and we’ll say, okay, this is good enough, where we’ve got it right now. In fact, perhaps we know it’s not good enough right now, in the room, but we know that everyone will away and then when we come back for the performance, in a few days, it will be good enough. We rely on everybody raising the bar and bringing their best to the table. I think that’s definitely a big part of what we’re trying to do there.

{audio:0:04:18} Which also links to making decisions in businesses, where you never have 100% complete information and, therefore, you have to make decisions with incomplete information – let’s say you have 60% to 70% of it – but you make a quicker decision?

{audio:0:04:33} Yes. For Shopify, for example, we talked a lot about making the best decision we can make, today, versus a perfect decision in the future, whenever that might be. One of the things that’s really interesting about performing in a jazz ensemble is that when you are up on stage, there is no luxury of stopping the performance and saying, hold on, we’re not sure about something; we need to work it out. You’ve got to keep going, no matter what happens. I think that’s a fascinating thing, being forced into those kinds of situations and being forced to improvise. That’s the thing that we talk about a lot, in jazz, which is that musicians improvise. But it’s something that we all have to do in our daily lives and in our work lives. There are always situations when you have to do something and you’re not entirely prepared for it; it comes sooner than you think or it was just totally unexpected. You don’t have the luxury of saying, hold on, I need to figure it out. You have to provide an answer or a solution now or soon.

{audio:0:05:41} I think Bezos has this framework of reversible or irreversible decisions, where you make, very quickly, decisions where you can change your mind or they’re not conclusive. But those that are irreversible, you have to be more prepared for?

{audio:0:06:00} Yes, definitely. You know, especially for those things that are reversible, that you are going to iterate. You know that you can try this and, if that doesn’t work, try something else.

{audio:0:06:13} I guess the big challenge is knowing what’s irreversible?

{audio:0:06:16} Yes. One of the things that’s interesting about performing music is that there is always this concept of structural stability. The worst possible thing that would happen is that it would go off the rails and everyone would get lost and the performance would totally fall apart. Obviously, you never want that to happen. That’s another interesting thing about jazz, which is that we value individuality so much. Jazz is so different from classical music, where there is a lot more uniformity and conformity. In Jazz, we often welcome individuals and people who are playing in a very unique style or a different way and we’re often trying to create situations, performing situations, where we bring in people that we’ve never played with before. But even though we’re doing that, the people who are performing, the good musicians, are always putting the performance of the ensemble first. They will never do anything to sacrifice that. They would never do anything that would cause it to go off the rails or turn into a chaotic situation.

{audio:0:07:25} How do you think about building cohesion between individual musicians, within an ensemble?

{audio:0:07:33} One of the things we talk about in jazz, is that we have this saying about people who have big ears. Not like Mickey Mouse, but people who have very high awareness; people who have very high contextual and situational awareness and high team awareness and high self-awareness. For example, as a musician, when you are playing your instrument, you have to have high self-awareness because you need to know, whatever techniques you are using to play your instrument, that it’s sounding right and everything is coming out the way you want it to. But of course, you are combining what you’re doing with this sound of what everyone else is doing. You have to be so aware; you have to be listening to that combined sound, all the time. You also have this other contextual awareness of what’s happening in the room, because you are performing for an audience and, in order to be connected to that audience, you need to be seeing and listening and watching what’s happening out there, in the audience, and how people are responding.

{audio:0:08:30} I think that really builds the cohesion is people who have that really high awareness and are not in their own little world. They’re really attuned to what’s happening in the rest of the team. Especially when you are doing something like jazz, it’s a very real-time activity and you have to have that on, all the time. You can’t go to sleep, even for a second, because you may miss things. It might be something that could be a critical thing that, if you missed it, would send it off the rails. But it also just could be something that might have made the performance better such as if one jazz musician played something interesting and was hoping that someone else might take that and respond to it and make something of it. It’s very much like that in improv comedy, for example. Someone puts something out there and someone else will take that and they will respond to it and they will build on it. You have to be really on the ball, looking and listening for those things. That awareness is really the most critical thing, in building the team cohesion.

{audio:0:09:29} When thinking of cohesion, how do you think about organizing musicians to drive creativity?

{audio:0:09:41} In jazz, for example, we don’t necessarily have the rigid structure that you have in some other ensembles. If you go and see a symphony orchestra, it’s very hierarchical in nature. There’s a conductor, typically, and then there’s different sections of the orchestra and each section has a principal and an associate principal and so forth. In jazz, the leadership is so much more fluid. You have to have people who are both good at leading and good at following.

{audio:0:10:15} When you watch a jazz performance, sometimes it’s hard to actually work out who is the leader, at any one point in time. Someone may organize the performance and someone may decide what they are going to play and someone may count off the tune. But once the tune begins, once the performance of a song begins, the leadership is moving around. So there are opportunities for everybody to provide creativity into the process. But of course, they also have to be fairly good and I think this is the most powerful thing – it’s that fluidity of being good at both leading and following and knowing when to pull back and when to take the lead and when to follow. I think that’s a critical thing.

{audio:0:11:03} How do you look at the parallels between fostering creativity in jazz, for example, versus business?

{audio:0:11:11} There are so many things there. One of them is, going back to some of the things I mentioned before, such as the flexibility and the fluidity within the organizational structure. For example, in organizations, having concept of a team but a concept of a team that is not fixed. I might be in an organization with 1,000 people and I might be a member of many teams. They way that those teams are structured, they might overlap and, also, they might be virtual teams; they might be teams that have just come together, to work on something and then they disband after that. One of the key things is having a very fluid organizational structure.

{audio:0:12:04} One of the things about the Ottawa Jazz Orchestra is, when we do different performances, we never have the same ensemble. We have different sized ensembles; perhaps even during the evening, we might change the ensemble in different ways. The actual grouping of the musicians and the way that they’re organized is often changing all the time.

{audio:0:12:26} The other thing that I think is really important, going back to that individuality and the team, is that having people who, even though they are strong individuals and have something unique that they are going to contribute and it’s probably the reason that they’ve been hired for the gig, they also don’t have much of an ego. They’re always willing to subjugate themselves and whatever individual thing they might want to contribute, for the good of the team.

{audio:0:13:06} Just on the point about fluidity and organizing teams and businesses, how do you balance structure versus no structure?

{audio:0:13:20} It’s a really tricky thing. For jazz, even if you look at different styles of jazz, there is something that they call free jazz, which is lacking in structure. Sometimes, musicians will go into a performance and they don’t have any clue what they are going to play, at all. They’re going to decide it on the spur of the moment and then it just takes form, organically. I’ve done performances like that, where we, pretty much, did that. We just went on stage and maybe we took a hint from an audience member or someone and we just started something and it just took shape. It’s entirely possible to do it. It’s also entirely possible to do it and have it be a total disaster and something that’s not actually very interesting or compelling to an audience, to the consumers. Because it can sometimes devolve into something that is just very introspective for the musicians and maybe they’re really getting into it and enjoying it, but the audience is not appreciating it, at all.

{audio:0:14:25} Constantly trying to have just enough structure is one of the most important principles. If I’m performing in a little jazz trio, the most exciting things happen when I know that we can take some risks and go outside and explore and do some things but, you always have to be aware of the structure and the possibility of things falling apart. Someone always has to be looking out for that and making sure that that doesn’t happen.

{audio:0:14:58} I think it just goes, very much, back to two things. One is, knowing what are the essential things that you always have to have. Secondly, having that awareness to always keep an ear or an eye out for those things. For example, in music, typically, you have time. You have a constant pattern going and you never want to lose that. If you start slowing down or speeding up, it sounds really weird and it’s probably going to result in something bad happening. No matter what they might be doing, even if the musician is going to some interesting, complex rhythms, they’re always trying to be very aware of the need for that and keeping the tempo and the beat and the groove always there.

{audio:0:15:47} It’s the same thing in business. We have things that we know are just essential, that always have to be there. If we keep an eye out for those things, that really helps a lot.

{audio:0:16:01} Do you see more companies adopting a more fluid org structure?

{audio:0:16:10} The problem we have is not a new problem. It’s gone on for many years and many decades and I’ve worked with small companies and I’ve worked with many big companies who wanted to become more agile and were going through agile transformations. So many of them truly had the best intent to want to get faster and get more agile. Not even just business organizations, but governments, as well. They try and a lot of them try really hard and, for some reason, they can’t seem to do it. The reason, generally, I see, is that the culture that they have is so engrained, that it’s so difficult for them to change that mindset. Even when, sometimes, there is initiative from the top of the organization, the problem is that you’ve got so many people, in some organizations, who have worked in a particular kind of way for years or decades. To get them to unlearn those things is pretty tricky.

{audio:0:17:26} One of the things that I think we saw at Shopify and the Shopify leadership realized fairly early on, is that as you get bigger, your culture is going to transform and there are some things that, if you lose them, they’re extremely difficult to get back. You have to really value those things and do as much as you possibly can to not lose them.

{audio:0:17:57} Can you provide some context to when you joined Shopify?

{audio:0:18:02} I was at IBM at the time and I’d written this book about jazz and about parallels between jazz and business and other domains and other disciplines. I also knew some people at Shopify. The thing that was interesting was that they had a role that they weren’t really sure what it would be called and they weren’t really sure what the person would do. They basically hired me into this role and, when I joined, I was a team of one. When I left, there were about 50 people in my organization. When I got there, I wasn’t even entirely sure, either, exactly what I would do. I just knew that there were things to be done and that they probably involved things around operational excellence and culture and learning and trying to help the organization keep those important things of the culture, such as the speed and the flexibility and the agility.

{audio:0:19:03} It really just evolved. It was a very short and brief job description, in the beginning. I would say, even when I got there, as things evolved over the years, it went in directions that I probably didn’t even know it was going to go in.

{audio:0:19:41} As you stepped into Shopify, what were the key lessons that you were looking to pass over from the book you wrote on jazz and the parallels with business and the kind of principles you used to approach culture and learning?

{audio:0:19:57} One of the things that was important in that organization and I think is important in a lot of small organizations – and it really should be important in every organization – is the concept of a learning organization. An organization where everybody is learning, all the time. It doesn’t matter what level you’re at, what experience you have; you’re always learning. Even when you hire people, you don’t just hire people for what they know today, but for their ability to learn, because everyone will have to do it.

{audio:0:20:37} Immediately there, I think that creates a mindset, where everybody is on this path of always trying to learn and accepting that they don’t always, necessarily, have the answer to everything. I think it also creates an organization where people are teaching one another and I think that’s really key. As I mentioned before about having people who are both good at leading and following, having people who are both good at learning as well as teaching, is crucial. In fact, one of the best ways to validate your own learning of something, is to teach it to someone else.

{audio:0:21:15} So the learning was always a very important thing. The other thing that was always key was the speed. One of things about going into an organization where you are trying to help organize things and, perhaps, try to bring some – now we use the word that some people never want to hear, the word starting with P – process. If you ever talk about process or structure, there’s a natural reaction of, I don’t want that; that’s going to slow us down. The thing is, there are good processes and there are good ways of working that can actually help speed you up. Those are the things that you want. You don’t want the things that are going to slow you down; that’s understandable. But if you can find the things that will actually be good and will help things go better and go faster, then those are the things we want.

{audio:0:22:10} There was always so much around education, of helping people to understand what those things are. Helping them to discover for themselves what those things are and implementing those things and not the things that would slow the organization down.

{audio:0:22:30} I think Shopify has two values which seem to define their culture, which are, innovation and experimentation. How do you really think about fostering innovation, whether that’s in a jazz ensemble or within a business team?

{audio:0:22:52} One of the things that’s important is that it can from anywhere. You don’t have this mindset that it only comes from some innovation team or it only comes from leadership. Anybody, in an organization, can have good ideas. In some large organizations, they will try to do things like, starting small, having a suggestion box; it could be a virtual suggestion box. Anybody, no matter where they are in the organization, can suggest something. One of the ways that they did it in Shopify, and a lot of other organizations have done similar things, is that they have these things called hack days. It would be a regular thing, every quarter; they would allow everyone to take a full day to work on any project they wanted. But what you would do is, you would actually propose an idea, a problem to solve, and there was actually a system to manage all this. You would try to bring other people to your cause; get other people interested in helping you solve that problem.

{audio:0:24:01} That could be a problem about anything. It didn’t have to be a problem about a product. It could be a problem that you wanted to solve or something that you want to make better, about the organization. Having something like that, that allows anyone to be able to present an idea and then experiment with it, test it, try it out, see where it goes, that’s a really, really powerful thing.

{audio:0:24:26} But it also has to be baked into the decision making of the company? You can always ask people to suggest ideas, but they have to actually do it. You have to actually consider it. How do you organize decision-making processes, to really take that into consideration?

{audio:0:24:48} One of the things that’s interesting is the idea that you take an idea, you do some work on it, you experiment, you test and you iterate on it and that the good things bubble up. You’re right because, in a lot of organizations, there’s often lip service around this kind of stuff. They’ll say stuff like this, but it just goes into a black hole, never to be seen again. That also means, in order to allow for that experimentation and allow for ideas to be developed and tested and so forth, that there actually needs to be time.

{audio:0:25:30} Various organizations, such as IBM, had their 20%-time thing. There’s lots of ways to do it but the organization has to definitely allow for it, in some way. That really means that, also, even if you look at it from a time perspective, it’s time to be spent testing those things and experimenting and trying out things, that’s not going to be time spent doing other things that, perhaps, are more predictable and more sure and may be operational things. Of course, you’ve got to keep the lights on and you’ve got to keep things running. But if you don’t allow for this time, to be able to do all this other experimentation and try things, then you’re never going to have the opportunities of what could come from that.

{audio:0:26:19} I always find it quite difficult to understand what a culture of innovation means. I can understand a culture of experimentation; that’s a bit clearer and a bit more practical. How do you look at a culture of innovation?

{audio:0:26:32} One of the things that’s essential is the difference between ideas and productizing those ideas and actually bringing something to market. Here’s the thing, I think in a lot of companies, and I think it was true at Shopify, there’s no end to the problems to solve. There are just infinite problems to solve. The question is, which ones are you actually going to put your time and effort into. Also, no organization exists as an island. When you have built up an ecosystem and you have partners, for example, and you have competitors and others in the space, there’s things where you sometimes have to say, you know what, this is a great problem; we could absolutely work on this and build a great solution to it. But we decide we’re not going to do it. We decide it’s actually better for someone else to work on this, for a partner to work on this or let a competitor work on this, for whatever reason.

{audio:0:27:36} Knowing when to say no, is an extremely powerful thing.

{audio:0:27:44} Often, organizations start talking about ways to measure the value of something, to measure whether something is succeeding or not. There’s a lot of ways to do that and always a lot of talk about metrics and data and analytics and so forth. So measuring impact, for an organization, is something that’s pretty tricky. One of the things that’s interesting for businesses is that, of course, the traditional way to measure is money. It’s revenue and profit and so on. In some organizations now, they’re realizing that that is not, necessarily, the best way to go.

{audio:0:28:33} You don’t start out saying, what shall we work on today? Let’s figure out the thing that is going to make us the most money. Ideally, what you would actually do is, you’d say, let’s figure out a problem that someone has and let’s figure out the best way to solve that. If we can produce a fantastic solution and a fantastic experience around that solution for a group of people who have a problem, that they will buy into that and that the money will come from that. But we don’t start out that way. That’s a really important, more indirect, route. Even just that emphasis on the experience.

{audio:0:29:12} For example, if you look at Apple and you look at what’s happened over the years, with the transformation of Microsoft, that’s what people have realized. In the beginning, people didn’t really understand what Apple were trying to do. But so much of what they’ve done and what they do, is all around experience. That experience is not just a product; the experience is everything. It’s like going to the Apple Store, and the App Store and all these other things. That’s really the thing that engages people; it’s not just the singular product and it’s not the specifications, the technical details. It’s the overall experience.

{audio:0:29:53} Let’s say that we have a business that is encouraging suggestions or ideas of new products and new problems to solve. You said that the hardest part is productizing that and bringing it to market. What are the typical processes or decision-making structures that you put in place, to bring ideas to life?

{audio:0:30:20} A lot of this stuff is really iterative. There are a couple of things. One is, definitely, understanding and deciding how you’re going to measure the success of something. How do you know that something is going well or not? We’re in something, we’re building something, in some project, how do we know that it’s actually going well? How do we know we would say that it’s not going well and that we would stop it? Honestly, I think a lot of the rest of it is very much iterating on that and also being open to a lot of feedback. The feedback is not just internal feedback, but it’s that external feedback. So many companies now, are much more open than they used to be, in terms of the way they engage with their markets and beta programs. All of these kind of early feedback programs are so critical now, for companies to be successful.

{audio:0:31:18} You can’t just do this thing now where you just build something, internally, and then just drop it out to market. You can do it, but it’s a lot harder.

{audio:0:31:26} What about the team structure?

{audio:0:31:31} One of the things that’s important with a of team structure is the multi-disciplined approach. Here’s a couple of things. One is that you realize that, generally, in any team, for that team to be successful, it’s going to have to have a balance of skills and experience in it. If I had a music ensemble, I’m not going to have five bass players, in a quintet; it just doesn’t really make sense. I need different disciplines to come to the table. So generally, if I was going to build any kind of a product, I’m going to have at least someone who knows a lot about the implementation and the building; someone who has an engineering mindset and, at least, someone who has a mindset about the experience and the design of it and someone who is going to look at the needs of the customer or the actual problem and whether or not we are building the right thing. That person might be more business oriented. So that’s one thing, to actually have those multiple disciplines.

{audio:0:32:35} Another thing that I think is extremely powerful is the idea that that is decoupled from the leadership, what you might call the project management, of who might lead a project. In Shopify, for example, we had this concept of Project Champions, who were people who run the project. It’s important to understand that that person is not someone who has the answers to everything; they don’t make all the decisions. But what they do is, they make sure all the decisions get made and they facilitate that. If they don’t know something, they will find out and they will find out who has the answer.

{audio:0:33:19} But the idea is that the ability to do that, that role, is totally separate from the discipline of the person. One interesting way to look at it is that if you look at a project and you say, okay, what is the greatest risk on this project; perhaps it’s a technical risk of building it? Maybe that’s going to be the hardest thing. Or maybe the hardest thing is going to be coming up with this fantastic experience that people will love. Maybe the problem is trying to figure out, exactly, how to scope the problem and bring it to market. Perhaps one way to go is to say, okay, if we think the technical problem is the greatest risk, perhaps we would have the person who is in that discipline who would actually lead the project.

{audio:0:34:07} That’s one way to go. Traditionally, in most organizations, they would have a project manager; it’s a professional role of someone who organizes the project. But often, those people aren’t actually doing anything on the project, other than organizing. There is often this tension that is created. This person is telling us how to do stuff and running stuff, but they don’t actually have any skin in the game because they’re not actually building parts of it. The idea that you would have someone leading the project who, actually, is one of the people working on building the thing, I think is very powerful.

{audio:0:34:48} If we go back to the jazz analogy, you don’t typically have anyone who leads a jazz group, who is just out the front and waving their hands. It’s always someone who is in the group, who is actually part of the process of actually building the performance.

{audio:0:35:05} A credibility thing with team members?

{audio:0:35:09} Yes, and also, almost an insider knowledge. They really know what’s going on. You don’t have that abstraction. Sometimes, when I worked in some other organizations in the past, especially big organizations, you see people who get shuffled around, who are managers of whatever. Last week, they were the manager of something and now they’re the manager of something else. They come to manage this thing and they have no background experience, knowledge or anything, about the domain at all. But supposedly, because they are a manager, it means that they can manage the thing. Sometimes, that doesn’t really go very well. It’s a powerful thing to think about leadership in a different kind of way.

{audio:0:35:58} In terms of organizing teams and, let’s say, you have this experimentation culture – Bezos and Amazon pioneered this approach, with the two-pizza teams – how do you look at organizing teams, to move effectively and efficiently, through decisions and productize ideas quickly?

{audio:0:36:26} There are a couple of things there. One is, at one extreme, we could say, we’re going to have teams and the teams can do whatever the heck they want. They can run things however they want; we don’t care, as long as it’s a success. The other extreme would be, we’re going to, forcefully, be very rigid and say, every team has to work in this way. Figuring out what the balance of that is, is a tricky thing. Ideally, you would at least be learning from successes and failures. If a team tries something and it’s a success, they would share that way of working with others and others would adopt it. Or if they did something in a certain way and found that it was a total disaster for them, then they would share that and other people would learn from those experiences.

{audio:0:37:17} Figuring out how you take the best of things and the worst of things and don’t do those things, is crucial. Then the other thing is the whole scaling factor. Of course, a lot of things are much easier when it’s smaller. When you have one or two teams and those teams are small, that’s one thing. Now do it with 1,000 people, 5,000 people; that’s a whole different story. That’s where tools and platforms can be very helpful. They allow us to amplify and to handle data and so forth, at scale. It becomes pretty obvious, to most small companies that, at some point, even though they might have tried to avoid it, that they need some kind of tool, to track what is going on. Even if it’s just spreadsheets, you’ve got to have something. You can just be having it all stored in your head and you’ve got to have some organization around it. It might even just be Google Drive, but you have to have tools and you have to evolve those tools.

{audio:0:38:28} One of the things that was powerful at Shopify, with the teams that I was working with, was that we built a lot of internal tools, to run the company. That’s what a lot of other companies, today, are doing. What’s also interesting is that there are a lot of companies out there, who build tools like that and they offer services. They will come to an organization and say, hey, we’ve got something that we think is going to transform your organization and will help you run your organization. Sometimes, those things can be useful and sometimes, not. If they’re just basic infrastructures, like Google Docs and those kinds of things, sure; most people need those. But often, what I’ve seen, is that companies that are trying to figure out how they run their projects and how they run their teams, often end up building their own stuff, internally, because it’s something that meshes very well and fully supports the way that they work and their culture.

{audio:0:39:24} Investing in that and be willing to build your own tools, without going crazy is important. That’s the other problem, some organizations will say, we’re going to build our own tool and we’re going to have our own this, that and the other. They spend forever doing and they go overboard with it and that’s not a good thing. That often ends up being a failure.

{audio:0:39:46} What do you think is the biggest challenge in scaling a culture of experimentation and innovation?

{audio:0:39:56} One danger is, definitely, not knowing how to say no; not knowing how to kill things and stop things. The extreme of this is, hey, we’re all going to experiment like crazy. Everyone is going to be doing stuff and we don’t keep very good tabs on it; we don’t understand what is successful. That’s definitely one part of it.

{audio:0:40:21} How do you get around that? Let’s say that you have so many different ideas and, as you said, you’ve got to prioritize them. Who actually makes the decision as to productizing or going the extra step?

{audio:0:40:35} This is something that a lot of organizations struggle with. The extreme, in a large organization, is that they will have very rigid, top-down structures and there will be a weekly directors meeting or whatever it might be and they are going to review every single thing. The other extreme is that you have no structure whatsoever. What I see in a lot of the smaller organizations, is that they try to avoid having anything like that but, eventually, they do realize that they have to have something. It’s trying to find a balance between a top-down and a bottom-up decision making. There has to be some balance in there. It can’t be just one or the other.

{audio:0:41:29} The other thing is figuring out how you actually measure. What are the metrics that we all agree on, that we’re going to use, to judge the success of something? Additionally, in order to speed things up – this goes back to the balance of top-down and bottom-up – you don’t just rely on top-down inspection or review or decision making, to stop things or correct things. What you want is teams that are auto-correcting, that have enough awareness that, hopefully, they realize, before it has to go up to a senior person, that something is wrong here; perhaps we should abandon this; this is not working. That comes back to awareness and giving people the tools to understand that. For example, here’s how you would measure something and if it looks like this, that’s probably not a good thing.

{audio:0:42:34} Are there certain processes that you would definitely put in place, for a company like Shopify, as it does scale from 500 to 5,000 employees?

{audio:0:42:50} In the beginning, even with most small organizations, have to have some kind of project management; you have to have some structure. At least, you have to have some common language around how you discuss what is a project, or whatever you are going to call it. What is the scope of the unit of work and how do we organize around that, doing it in such a way that you don’t force people? You don’t say, every team must have this kind of person and this kind of person. You say, in order to be successful, every team should have a balance of experience and a balance of skills and perspectives. You’re giving people the guidance and, hopefully, they are making good decisions, based on that.

{audio:0:43:52} I think one of the things that is important is the getting away from the rigid, one-size-fits-all, this will always work. It’s hard, because in some organizations, they’ll ask questions and they want a simple answer. Often, the answer is not that simple. The answer is often, truly, it depends. That doesn’t mean that you can’t give any answer, but it’s often better just to give guidance and principles upon which you make decisions, rather than trying to give solutions all the time.

{audio:0:44:33} How do you think remote work could impact scaling culture?

{audio:0:44:39} One thing is definitely around the tools. Let’s say in the last decade or so, there’s been a lot of technology developed, to help people work remotely. When I was at IBM, for example, we ran global projects, with hundreds of people across the world, in all different time zones and it had a lot of challenges. But we made it work by having tools. In fact, one of the projects I was working on there was actually developing tools to help companies do that, so we were using the stuff ourselves. Having the tools is really helpful and, I think, necessary now. What we’ve seen, since the pandemic, for the companies that weren’t already there, they’re now having to figure out, what do we need and how do we use it.

{audio:0:45:43} The other thing is the whole culture around the trust factor. A lot of organizations never wanted to allow people to work remotely or to work at home, because they don’t trust that the people are actually working. In the end, the only thing that really matters is the impact you are having and the success that you are having or not having. It doesn’t really matter what hours you are putting in. Obviously, there is a core responsibility that you have, to be there for your team and to interact with your team at certain hours. But apart from that, the only thing that really matters is the results that you’re getting. That’s a pretty hard thing, for some organizations to take that step, if they’ve been stuck in the past.

{audio:0:46:38} What’s been interesting is that now they’ve been forced to do it. There’s been no choice about it and so now people are working at home and they’ve had to make this jump. At some point, there will the option that they could, in theory, go back to the office. But will that really happen because there are, clearly, benefits and, in some cases, organizations have said, oh, we didn’t think this was going to work but, actually, it does work.

{audio:0:47:11} With a company like Shopify, for example, which is growing very quickly, fantastic product platform and customer service and will continually have, as you said, so many different jobs to be done, for the consumer; so many more potential different product lines or product areas. How do you really maintain a culture of innovation and experimentation, when you have so many different product lines or opportunities to go into?

{audio:0:47:43} One of the things that’s interesting for a company like that, is trying to figure out, at what point do they actually stop. In business, we always talk about growth; that’s what everybody wants. Everybody wants their start-up to be this huge success and that they have thousands, tens of thousands, hundreds of thousands, millions of people and customers and dollars and so forth. But what’s the point at which it’s actually not a good thing?

{audio:0:48:18} Of course, some organizations start to do things like spin it off into a separate company. There have been all these experiments that have taken place, in some organizations, with spinning it out, spinning it back in. For many companies, it’s about figuring out when to actually stop and say, you know what, we’re actually starting to go a way that’s not helping us. In a way, it’s great, it’s exciting to grow but it’s not necessarily a good thing. Even culturally – this is nothing specific to Shopify – every small company, as they grow, things will change. For some people, those changes are positive and for some, they’re not. Some people will leave an organization because it’s not for them. They were happy working at a small company and they’re not as happy working in a larger company. They prefer smaller companies, smaller teams. Some people are always going to leave because of that kind of a situation.

{audio:0:49:32} Is there anything that really sticks out to you, that was different about the behavior of Shopify, as an organization, versus IBM, in terms of culture and, as a business?

{audio:0:49:51} The main thing is really the openness to learning and building that in, from the beginning. Everybody in the organization, even the leadership, setting the example of, we don’t have all the answers; we’re figuring stuff out and we’re learning, just like everyone else. It’s also the willingness to make hard decisions, quickly. In a lot of organizations, there are things that just drag on, forever. In the meantime, there are detrimental effects, so being able to make those decisions is pretty critical.

{audio:0:50:36} One thing that was interesting was, even just seeing, just recently, at the beginning of the pandemic, Shopify announced that, even after the pandemic was over, they were going to continue working from home. They were going to be a fully remote company. They made that decision pretty early on.

{audio:0:50:54} Tobi always seems to be at the forefront of these decisions and taking the plunge much quicker than others, it seems?

{audio:0:51:03} I mentioned about that mindset of being very open to things. One of the things, for these younger companies and younger leaders, is that they have a strategy for where they want to go or, at least, they have a direction, they have a vision for where they want to go, but they fully admit that, exactly how they’re going to get there, they don’t know that. In business, we’ve always had this idea. Sometimes, you’d actually get asked, if you were looking for investors, what is your five-year plan? To say, we don’t have one, that might have been a bad thing at some point. But there’s the reality there now that, oh, it’s okay to say that because you could have one, but it’s BS. Who knew what was going to happen, with what’s happening now? Nobody knew this was going to happen and it’s changed the world. So you can say that now, but that doesn’t mean you can’t have a vision for what you want to achieve.

{audio:0:52:23} Yes, but you have to be open to how you’re going to get there. For sure, you probably know it’s not going to be a straight line. It’s going to deviate, here and there.

{audio:0:52:38} It almost seems as if he is empowered by being humble and not knowing; it’s quite paradoxical.

{audio:0:52:50} That’s a very important example to set, for an organization. It’s like going back to what I was saying about the jazz situation. We always want to bring in people who are individual and are bringing in unique ways of thinking and a unique style of playing. But those people have to be really humble. We never want people who think that they have all the answers. It’s pretty powerful, in an organization, when you have a senior leader who is able to say that and really be open to ideas coming from anywhere.

{audio:0:53:30} How would you look at Shopify versus Amazon, for example? Amazon have been the pioneer, as we said, in this decentralized structure and they constantly seem to be innovating, bringing new products, focusing relentlessly on the customer. How do you look at the parallels?

{audio:0:53:53} There are different stages, in terms of how long they’ve been around and how they’ve scaled. I will say this, Amazon – and I don’t think this would be a surprise to most people – the business is, and has been for quite a while, very much around operational efficiency. They’re trying to squeeze every last cent that they can out of the system. When I was at Shopify, I never saw that kind of thinking around the dollars and the cents. It was there, certainly, and there were people who are in finance, there and it is their job to think about that. But it was never really about that. It was always, much more, about identifying interesting problems and solving them, in a unique way and in a way that would be a really awesome experience for someone. But yes, they’ve been a huge financial success and I think that’s a telling thing.

{audio:0:55:18} How do you get a sense if someone is an effective or lifelong learner?

{audio:0:55:31} Feedback is one of the things that’s interesting, for a number of reasons. One is that, when you ask people about the idea of positive and negative feedback, they think positive feedback is good. Most people’s idea of it is that it means that I do something and someone tells me, good job. And negative feedback is, no, that’s bad. The idea is that positive feedback is good and negative feedback is bad. If you study systems theory and you study biology, there’s this idea of feedback loops and that the negative feedback loop is, actually, a correcting feedback loop. It’s the idea that, when you are doing something that is, perhaps, not helping you, that you would actually get some correction and that would be a good thing.

{audio:0:56:30} To have that mindset that you are always looking for the negative feedback, that’s a pretty powerful thing. I’ll give you another analogy. I’m a wildlife photographer; I spend a lot of time teaching photography and doing photography and I’ve seen many people who have been doing photography for years and decades. Some of them haven’t gotten very far at all or are, actually, perhaps worse photographers than when they started. For a lot of them, they will post their photos on Instagram or some other platform, where all they ever get is, hey, that’s awesome, fantastic, love it. No one ever says to them, I like how you did that, but did you think about doing this. Since they’re also never going and asking for that feedback, they’re in such a different place. Sometimes there is not even the awareness about the idea that what they’re doing might not be the best way to do it and that there might be a better way.

{audio:0:57:44} Just that willingness to be open to feedback and actually seeking feedback and seeing feedback as a gift, when you get it and not seeing it as a critical thing and refusing it, for example, that’s a hugely powerful thing. That’s not even just to do with business. You can find that in any discipline, in so many areas of our life and our work, people who are open to feedback and always take it. I work as a professional photographer and I teach people, but I also go and sometimes even pay other photographers to give me feedback on my work. They may see things that I don’t see and that’s a really important thing, if I’m going to get better.

{audio:0:58:35} How do you get a sense for that, when you are interviewing or hiring someone?

{audio:0:58:42} One thing that is very powerful is going back to some of that awareness and beginning with the self-awareness. When you talk to people, it’s not even so much the questions that you ask and the answers you give them; it’s the way they conduct themselves in the interview. Sometimes, the lack of self-awareness is actually quite interesting. When people are speaking and they are not even aware of some of the things that they might have said or the way that they might have said it, maybe putting their previous organization down. Or they will describe a situation and you get the sense of, okay, this person doesn’t take responsibility for things; it’s always someone else’s problem. It’s a very hard thing to judge but the more that you do it, you understand it more.

Shopify: Creativity at Scale

Former Director of Getting Shit Done at Shopify

inpractise.com/articles/experimentation-speed-org-structure

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Adrian Cho

Former Director of Getting Shit Done at Shopify

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Shopify: Creativity at Scale(July 6, 2020)

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