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ROB magazine

CEO of Evernote. Former head of Google Canada and general manager of Google's moonshot factory. One-time Canadian Tire grunt

Working at our parents' Canadian Tire store in Goderich, Ontario, was a requirement for the O'Neill family. My brothers and I would race to see who could build bikes and barbecues faster, and challenge one another to sell the most obscure fishing lures. We got good at making up stories.

I think everyone should work in retail or as a server at least once. You learn a lot about how to treat other people, and you learn the value of hard work.

I moved to Silicon Valley in 1998. I was there before, during and after the dot-com boom. If you think about the things that were promised back then, retail was going to be completely transformed. Now we're starting to see that happen. The big trends take time to evolve—they are often overhyped in the short term and underhyped in the long term.

Google is a once-in-a-generation company. I'd been there for five years before I came back to Canada to lead the operation here. That's where I learned how to rally a team around a common purpose and vision, and really pay attention to the culture.

Google X, or the moonshot factory, is a place where you dare to dream the impossible. The only way you disprove something is if the physics don't work.

There's an expression, "Creativity loves constraint," and I think that's part of the ethos of Google—constraining a problem and being rigorous about evaluating things along the way and not being afraid to fail.

Google famously talks about 70/20/10—70% of time, energy and resources goes into the core product, 10% goes into adjacencies or extensions, and 10% goes into those moonshots. It'd be great if Canadian companies took 10% of their resources and said, "We're going to place some bets, and some, if not most, of them will fail, but the one or two that do succeed will more than offset the investment."

Evernote is a freemium business model. The vast majority of our users use the product for free. For us to make money, we have to deliver value over and above the free product. If we don't, we don't have a business.

There's a global war for talent, particularly in Silicon Valley. Identifying and recruiting great talent, and developing and retaining the talent we have, is the single biggest use of my time.

I'm looking for people who can subsume their own ego. I think this partially explains why Canadians punch above our weight in leadership roles—it comes naturally to us. When I was growing up in a small town, if you got too big for your britches, you're either told or you're physically told.

We try to keep our hiring process as free from bias as possible. It's quite amazing how subtle biases can be. So every job description written at Evernote goes through a company called Textio that detects biases. Then we rewrite them.

I have to work with all sorts of stakeholders, including the Trump administration. The one policy I really have trouble with is immigration, which I just respectfully…unrespectfully—I just disagree with. It's so critical to the success of the Valley.

I have two kids, and my 12-year-old was the only kid in his class who didn't have his own phone. There's a sense that the world is designed to feed addiction to technology, and I worry about that as a parent.

When you care deeply about somebody, your obligation is to give them direct feedback. That's true of being a parent, and that's true of being a leader. Even when it's hard. Especially when it's hard.

This interview has been edited and condensed.