Some people are born to lead. You can see it at an early age: the charismatic girl at summer camp who everybody follows off the end of the dock, or the boy in Grade 8 who always gets picked first for the sports team. Many entrepreneurs have that gene, too: it’s what makes us able to sell an idea to investors, a job to employees and, ultimately, a product to consumers. From my time at a handful of startups, I felt I had a decent amount of experience when it came to leading and motivating a team.
Then, six-and-a-half years ago, I joined Shopify—a commerce platform for retailers—and that misplaced confidence in leading a team came to an abrupt end. I was now managing a half-dozen people, and much to my surprise, not everybody thought the same way as I did. It was challenging when people weren’t always able to see the big picture right away and sometimes got caught up in details. At the same time, I didn’t trust others to do their jobs so I ended up micromanaging them. Worst of all, I was taking my problems home with me, putting strains on my relationships.
Shopify’s CTO at the time was working with an executive coach and tried to get me to go. I was doubtful. I’d been a human Swiss Army knife for so long, used to doing everything on my own—so why would I need help? But I took a chance. Today, I’m responsible for around 1,000 people, directly and indirectly. And I can say, without a doubt, that booking that first appointment with my coach Cam Gregg was the smartest business decision I ever made. Why? Here are three big lessons I’ve learned and reasons I keep coming back:
1. Leading is not the same as managing. I spent most of my life as an entrepreneur leading and inspiring others, but I never learned how to manage. One of my earliest and biggest revelations was to appreciate this difference. Managing is a long-term commitment that requires enormous patience and the steady building of trust. It’s not as flashy as a big investor meeting or landing a huge client. But the returns on this kind of commitment can be enormous. Case in point: In my early days at Shopify, working with just a tiny team, my first reaction to problems was just to fix them myself because it was quicker and more efficient than teaching someone else. But Cam helped me see the limits of that way of thinking. Scaling requires that, as a leader, you invest in people and put faith in their abilities, not yours. There’s no way I could manage nearly 1,000 people today without appreciating that distinction.
2. The sooner you learn that differences of opinion are a necessary asset, not a liability, the better. As a young entrepreneur, if I walked into a room and everybody agreed with my ideas, I felt great. But working with a coach has allowed me to see the value in differing opinions and working styles. I work best under pressure and in a slight state of chaos, but others are more cautious by nature and question big risks. Working with a coach, I’ve learned, well, the art of empathy: the ability to put myself in someone else’s shoes and accept differing points of view. And you know what? I now have tremendous appreciation for those who question and challenge me on some of my plans. By poking holes, the end result is often 10 times better. Today, when I walk out of a meeting and everybody agrees with me, I get really nervous.
3. The benefits of an executive coach extend beyond the office. This past June, I became a father for the first time. Having a daughter has helped me reflect upon my priorities—and the need to find a better work-life balance. That’s hard when you’re in startup mode and working 80- or 90-hour weeks. I used to go home at 6:30 p.m. but was never really off the clock—constantly answering emails and calls from home. Now, I leave the office later but commit to being present once I’m home. I also stopped filling my calendar with back-to-back meetings and blocked out two hour-long slots each day to think, to physically move around the office, meditate and to connect with people serendipitously. That’s something I worked on with Cam, and it’s made me a better leader, husband and, I hope, father.
Shopify now has 12 on-staff coaches—what we call the talent acceleration team—who are helping guide our company’s managers. Yes, some people are born natural leaders, but no one is born a good manager. That has to be taught and practiced. Today, I can honestly say I still have a lot to learn about managing others, but at least I know what I don’t know. I think that’s progress.
