Leadership lessons from Foodee and Tacofino My first job was scooping ice cream at the local baseball stadium. I put myself through college as a caterer and server. Not so many years ago, I joined a startup called Foodee, which at the time was just five people. Since then, Foodee’s become a leading food-tech company, delivering over two million office catering meals in more than a dozen cities across North America. I am also the co-founder and co-owner of Tacofino, a 10-location local restaurant chain that started with just one food truck. I’ve learned a lot about leading teams through wins and losses, crises and day-to-day operations. Much of this came to light in a recent conversation with the University of British Columbia for alumNIGHTS: Leadership Lessons. For those of you that weren’t able to attend, watch the short recap video here.  I’d like to share some of my most valuable leadership lessons, including tackling the ever-present imposter syndrome.

Know thyself: Understanding leadership styles and personalities

Leadership styles grow out of personality traits or circumstances. If the first, then that leader seeks to understand the individual. If the latter, then that leader must consider what part of a situation—be it a win, loss, crisis or downtime, for example—requires a certain response. When I first started leading a team, I let my extraversion overpower introverts. Extraverts got more airtime. I had a misconception that leadership was about extraversion or alpha qualities. That one is a “born leader.” This is untrue: there is great power in diversity and differences in communication styles.  Misalignment can come from many places. Likewise, the discomfort that it creates can be an opportunity for growth. Seek to understand where it comes from. Everyone, yourself included, has various strengths, weaknesses and personality traits. Get to know yourself and how you lead and get to know your team. Find your collective strengths.

End goal: Getting to the situational leadership style

There are many different leadership styles that one will develop over time. A crisis manager, for example, will lead by enforcing steps out of necessity. “Do this today or there won’t be a tomorrow.” Among the many hats you may wear—collaborative leader, coach or, at the highest order, visionary—circumstances will arise where you will learn new leadership styles and skills.   For me, the Holy Grail of leadership is the situational leader. This comes after years of experience and working through many complex scenarios. Draw on that experience and bring wisdom to the table depending on what’s happening and with who. Wear a different hat for every occasion.

Habits, discipline and progress

I recently read Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear. He uncovers just how many habits we have on a given day and the ways to identify them as either serving our goals or not.  Habits are more prevalent than we think. We are habit-forming animals. We get up every morning at the same time and get ready for the day in much the same way. These are neutral habits. James Clear talks about good habits that are viewed as “discipline” and bad habits are “additions.” Consider your daily habits. Which supports your goals? Which are mere additions that we should cut? Designing your environment to support good habits and progress. My habits are constantly changing, but they are improving over time and with effort.

Imposter syndrome: How to avoid it

I am in a state of constant learning to “become a good leader.” Even with each success—or failure—and the growth you hope it brings, the imposter syndrome never really goes away. That’s normal. For example, when I accepted the role of CEO at Foodee, a ridiculous title at a five-person company, I was doubly confronted by imposter syndrome. Because back then, I wasn’t sure that I should be leading a company of any size. As soon as I had mastered that level of organizational ‘complexity’ though, we grew the team and I was challenged at the next.   The Peter Principle, that you’re often promoted past your last level of competency, is as real for leaders as it is with anyone. I try to overcome this by always comparing myself to who I was yesterday, not to others. In the end, as leaders, we must guide our teams with the same qualities, habits and standards that we expect from them. If we lead with our strengths and are humble about our weaknesses, maybe our teams will do the same and no one will feel like an imposter.