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?

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.

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.

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.

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.

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?

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.

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.

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?

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.

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.

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