Shopify: Creativity at Scale

Former Director of Getting Shit Done at Shopify

Why is this interview interesting?

  • Parallels between organizing a jazz ensemble and corporations
  • How to foster new ideas and creativity within an organization
  • Challenges to scale and maintaining a creative culture
  • Shopify's culture of experimentation and speed of decision making
  • The importance of productizing ideas
  • How to hire lifelong learners

Executive Bio

Adrian Cho

Former Director of Getting Shit Done at Shopify

Adrian has over 30 years of experience working for both small and large organizations including IBM, Fujitsu, Bankers Trust, and Shopify. At Shopify, as the Director of Getting Shit Done, he started and led a business unit that helped the company through a critical period of hyper growth by accelerating and becoming more effective at scale through the growth of culture, hacking process, coaching people and teams, and building automation to reduce friction. Adrian is also a musician who has been performing for over forty years, he is best known as the Artistic Director of the Ottawa Jazz Orchestra, a unique, critically acclaimed symphonic jazz ensemble he founded in 2006.Read more

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Interview Transcript

Adrian, could you share your experience in jazz and your role as the artistic director in the Ottawa orchestra?

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.

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.

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.

Do you think that limiting that preparation time actually drives more collaboration and more creativity?

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.

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.

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?

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.

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?

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.

I guess the big challenge is knowing what’s irreversible?

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.

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Shopify: Creativity at Scale(July 6, 2020)

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