IV.14.2023 - Leadership Lessons that Jack Taught Me
Over the course of my career, my thoughts about effective leadership have evolved with experience, relationships (good and not so good), and my own research. My experience on Toronto’s “Bay Street” allowed me to work with C-level leaders in a variety of positions across Canada. I started as an entry level Marketing Administrative Assistant, but I was quickly exposed to challenging situations beyond my pay grade that accelerated my professional development. I quickly became aware about who I felt at ease with and who made me feel uneasy, on-edge, and, at times, intimidated.
In 2015, I was getting ready return to work after my second mat-leave when an Executive Assistant position was posted. I would be the right hand of two new Senior Vice Presidents based primarily in our Toronto office, with occasional time spent in Montréal. When I expressed interest, my past success resulted in bypassing the interview process and moving straight to negotiations. The 30% salary increase, and 6 weeks’ vacation time exceeded my expectations. And that’s when I met “Jack”—one of my new bosses.
According to 
Byrd Baggett, author of Dare to Lead, the typical reasons that people feel the need to control are lack of trust, lack of confidence, ego/arrogance, and perfectionism (I saw Jack’s picture when I read this section of the book). Jack was pleasant when we initially met. I could tell he was eager to delegate things right away and I was eager to get started. But my discomfort working with Jack grew with every interaction–it was like my presence was an inconvenience to him. He never said ‘please’, rarely said ‘thank you’, and never expressed any appreciation for my work. There were several times when Jack and I would be mid-conversation and he would push me aside when someone “more important” would appear and I would be left hanging. It didn’t take me very long to conclude that Jack was not a nice man, but he was also a lousy leader. Lesson learned.
It’s unfortunate because Jack was very smart—brilliant in some ways—but he always considered himself the smartest person in the room and that worked against him. Now that I am a leader, my time with Jack was instructive. I have learned that asking questions, keeping an open mind, and being respectful of other people allows me to lead with confidence, support, and integrity. In Dare to Lead, some of my favourite questions/phrases are:
What do you think?
I appreciate you.
Thank you.
These three simple questions demonstrate that you are open minded and considerate about what other people bring to the conversation. Control and intimidation don’t work. Employees will second guess themselves to the point that their performance deteriorates. And some people may just leave (or worse, they quit and stay). Effective leadership is supportive, empathetic, and versatile.