How to Be a Leader, Shopify Style

Self-actualization, that thing at the top of Maslow’s hierarchy of needs: “what a person's full potential is and the realization of that potential.” Shopify cares deeply about growth, and aims to be a company where its people reach the self-actualization level of the pyramid. I think that’s pretty special, and it’s just one of the things that leaders need to manage during their time at Shopify.

For the last few months, I’ve been participating in what we call Lead Level Up. I’m not formally a team lead yet, though I have been in a bit of a leadership role and should become a team lead eventually. A lot of what we learned in the all-day kick-off is general enough to share, so I’m going to highlight the things that resonated with me the most. Most of what follows comes from our CEO and co-founder Tobi’s presentation that day.

An interesting fact is that Tobi and his co-founders/early employees didn’t know how to be managers. It was an entirely new skillset. Tobi admits he was not a natural manager; he found it difficult losing the tight feedback loop you get when programming. He admits he fought often with the others in the early days until they sat down and decided to respect each other by committing to being honest and improving their feedback.

Tobi ultimately believes that he was able to improve his own management skills by learning how to better give effective feedback. Everyone is bad at this at first, and there is no limit on how much better you can get. It can be really difficult to take feedback as the gift it is because your ego is so tightly wrapped in the exchange. When I was an instructor at Carleton, I learned how hard it can be to give good, honest feedback, especially if the other party (students, in my case) don’t entirely trust that you have their best interests at heart. I’m now learning to give feedback with radical candour.

A major tool that will help any manager is trust. Trust is more nuanced than a binary relationship. Trust exists between departments, and is fundamental to being highly aligned and loosely coupled (that is, fast-moving teams with high autonomy working toward common goals). When you start seeing a large amount of process being introduced, it’s usually because there is a lack of trust. Process is a prescriptive solution to a problem that isn’t terribly intuitive. It’s a bit like baby-proofing.

After trust is established, the manager’s job is to make their team better every day. If the team is not getting better, it is getting worse. Questions a manager can ask include whether they can remove any ambiguities or dependencies, have they helped someone have a breakthrough, etc. Focus on the high leverage activities that yield the greatest output for your team. Teaching, for example, is high leverage in all its forms. One-on-ones, while important, may generally not have high leverage.

Speaking of one-on-ones, how do you make them effective? Have them at least once a month. Take notes. Find your own style. Use them as a learning opportunity, and a chance to understand the other person. There will be hard situations, and they are only solvable if you have an extremely good read on all involved. Crucially, you must give good, honest feedback. And if you ever hear during a one-on-one that you have made a massive, positive contribution to someone’s life, then you know you’ve made it as a manager.

As mentioned above, managing is an entirely new skillset. Become well-rounded, focus on personal growth, read a lot (e.g. High Output Management and Thinking Fast and Slow). Become the guidance counsellor, the coach, the shrink. Help get yourself and your team to self-actualization, and you’ll do just fine.