How do you look at the parallels between fostering creativity in jazz, for example, versus business?

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.

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.

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.

Just on the point about fluidity and organizing teams and businesses, how do you balance structure versus no structure?

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.

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.

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.

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.

Do you see more companies adopting a more fluid org structure?

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.

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.

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