The Diary of a CPO - Chapter 2
What I wish I knew when I was in my 30’s.
The Diary of a CPO - Chapter 2
What I wish I knew when I was in my 30’s.
When someone opens that door for you, walk in.
When that person believes in you, believe in yourself.
When that person now puts their trust in you, get the job done.
What I wish I had known then that I didn’t know in my 30’s.
People say everything happens for a reason, but when I was younger, I didn’t see things that way. In my early 30’s, I was working as an admin assistant for one of the largest companies in Canada. For a long time, I was unsure what I wanted to do with my life career-wise and I was also trying to figure out what I was good at. Back then, feedback wasn’t given as readily as it is today, and perhaps it was a disservice to myself to never ask for it but it was a different time and you just got used to how things were done because you didn’t know any better.
My job wasn’t very difficult but at the same time, I put in a lot of effort to do a great job. I came in really early at 7am and worked through my lunch, leaving most days at 6pm, starving. I wanted to learn as much as I could in my job so I took on tasks that could help me develop myself. The more I took on, the more my manager would give me and while it often made me uncomfortable (like the time she told me to facilitate the Senior Executive Leadership team meeting), I did it. (Note, the leaders that were in those meetings I facilitated went on to become some of the greatest CEOs in the country - if I knew that at the time, I would never have had the courage to lead any of those meetings!).
During this time working with this leader, she didn’t lead a team directly as she was in a new role as a Privacy Officer, which was a new compliance requirement that was introduced as part of the new privacy laws in Canada, so it was just the two of us. She was often in meetings from morning to end of day so I worked alone most of the time. The HR team worked on the same floor as me and they often invited me to their team meetings or outings since I didn’t have a team to work with.
One day as I entered the elevator to go up to the 19th floor, a very tall man in a fancy suit and white hair jumped into the elevator with me. I froze, scared to look over. In my mind, I was sure he was our company’s CEO and Chairman. I nervously cracked a smile as he pressed the button to the 20th floor (the executive floor).
The gentleman looked over at me, cocked his head and smiled. Just a deep, genuinely friendly smile. I smiled back. He then looked at the Burberry purse I was carrying and asked, “May I ask where you purchased your bag?” I looked down and thought about it for a while, then looked back up and shared the luxury department store that I had purchased it from.
When he heard that name (which was privately owned by his family), he clapped his hands together and said “Yes! I was hoping you would say that,” and beamed with happiness. I never imagined my first interaction with the CEO and Chairman of this great company would be like this. He was so lively, so interactive, and I could actually make this man genuinely smile. At that point, my elevator stopped on my floor and I got out while saying “Have a nice day.” I stepped out of that elevator in awe. What a nice man, I thought walking away.
Two weeks later, the VP of HR called me into her office. I stepped in cautiously and wondered if I was in trouble. She asked me to sit down and shared that she was hiring for a very important role which was Executive Assistant to the Chairman’s Office. I was wondering why she was telling me this. She told me that I would make a perfect candidate for that position. Executive Assistant? I told her that I wasn’t interested in being an executive assistant (mind you, the CEO had a literal team of EAs and I would be the third addition). She looked at me and said with a smile, “Christine, you don’t understand. People can’t apply for a job like this. You’ve been summoned.” I told her I needed to think about it and walked away. I went back to my desk and sat down. Was I being “summoned” for this role because I had made a good impression to the CEO in the elevator recently? That seemed absurd. Was I being considered for this role because I was already an admin assistant? Most likely, I thought. Here I was trying to figure out what I wanted to do with my career and now I was following the path of an assistant for life. My mom used to say to me when I was a kid, “If you don’t get a good education and job, you will end up being a lowly secretary fetching coffee and dry cleaning for your boss.” That was the immigrant nightmare, that you would live your whole career taking care of someone else. Ugh, I was torn. Should I just decline this role or take a chance and see what it’s like? It’s not like I was loving what I was doing right now but at the same time, I was unsure what the role really entailed.
The 20th floor seemed like this great mysterious place that not many people were privy to visiting. There was an elevator that went up to the 20th floor, but also a massive, clear, lucite round staircase that swirled from the 19th to the 20th floor. And the carpets leading there were pure white! Imagine that, white carpet for an office with employee foot traffic (think about those muddy winter boots). We had an exceptional office manager that would chase you down if you had muddy boots trailing to your desk so we were all on high guard in those days.
I decided to talk to a few HR leaders at the company to ask what I should do. Their advice was to take it! “Why,” I asked. “I don’t want to do administrative work as a career.”
“Don’t be silly,” they said, “This is a gateway to do whatever you want after you put in your time. You will learn so much about running a business like this, especially right by the CEO. This is a privilege.”
I never thought of EA work as a “privilege” but somehow anyone I talked to seemed to think this was a job of a lifetime. So in the end, I decided to take that job. I let the VP, HR know that I would give it a try but on one condition - I wanted to be seconded into that role for a year and then I wanted the opportunity to return back out of that role if I wanted to after 12 months. It was a deal!
My first day on the job was surreal. I walked out of the elevator onto an immaculate floor of pristine white carpet and marble stands that showcased dozens upon dozens of inuit art (he had one of the largest collections in the country). If you looked down the glass banister to the floor beneath you, you would see a magnificent totem pole that towered from the 19th floor all the way to the 20th floor (it was rumoured a First Nations Chief gifted this handcrafted totem pole for him, of which it had to be sawed in half in order to bring it into the building elevators and then reattached in all its glory once it found its new home). I started my morning sitting in the CEO’s walnut paneled office which overlooked midtown Toronto from its octagon shaped building.
What would this successful business icon want to chat about with me? I was so nervous.
Surprisingly, he was so kind and genuinely interested in me as a person. He asked me where I went to school and I told him York University. In my mind, I imagined he was probably thinking, “Oh, you didn’t attend an ivy league school? Pity,” but rather, he said, “That’s wonderful, York University is growing so rapidly, what a great school!” Then he asked curiously, “What did you major in?” I replied, “English Literature,” knowing that he would probably have expected a business major, but surprisingly, his face brightened and he said, “English literature is a fantastic major to take! What a wonderful choice!” He then shared how his daughter had taken English Literature herself. I suddenly didn’t feel so ashamed about my choice in my major that day.
As we chatted, the other EA let him know that the CEO of BMO (Bank of Montreal) was on the line. “Tell him I’ll call him back,” he replied and he directed his attention back to me. He told me that his family was very important to him and his one request was that if any of his family members needed help with something, would I be kind enough to support that. “Absolutely,” I said. There were 4 sisters, all older with him being the youngest in the family and they all lived relatively close to the office. On any given day, one particular sister would come into the office, greet everyone kindly on the 20th floor and often bring fresh cut tulips for me, wrapped in a wet paper towel. She would let me know she picked them fresh from her garden. She was so kind, as were all the sisters.
He also gave me some great advice early in my career. He told me that I would be interacting with his closest executives, family, friends and business associates. He shared that how I represented myself would be a direct reflection of him. I understood what he meant and assured him that I would be professional and accountable, but that’s not what he meant. He said it was more important to be kind because even though I had no authority or power to make any of these people do things on his behalf, by being kind, it would influence them to want to do things on his behalf. I learned later that some people that worked for him liked to have a habit of “name dropping” and demanding attention while I simply wanted to avoid it. It was the best advice someone as powerful as him had ever given me. A lesson in life about how to interact by one of the most powerful people I had ever been surrounded by.
Over that year, I was tasked to do random things that were all part of the job. I recall he asked me to record a new voice message for his home telephone, which I did. The next day, he said I should record a voice message for all his residential phones because I sounded the most friendly.
Other times, I was responsible for responding to personal letters that were sent from business billionaires, royalty or movie stars. When I responded to these people, I drafted the letters as if I were him and then he would review the responses. To my surprise, he loved my responses and he would simply sign his autograph to each typed letter confirming they were good to go out.
Did you ever watch “Devil Wears Prada?” Oftentimes, I felt like I was Amanda Sachs (Anne Hathaway) who at any given time, would need to remind him of names of people who were visiting him throughout the day, or remind him of which pop star might be chartering his private jet over the weekend for the TIFF he hosted. The only thing is, he was never that character, Miranda Priestly. Rather, he had a great sense of humor, he shared how he felt about things that troubled him, and he would occasionally call me over to teach me something new like how to read stocks on the market or inquire whether I knew how to golf. Just fun things that he would randomly suggest when he had some time to kill before his next important meeting.
Eventually he connected me with his house staff in Toronto, his house staff in London, England, his VP, Operations at his luxury department store in Ireland and England, his concierge and team in Florida - every team that he worked directly with when he flew out to different locations for different seasons of work. He always connected me with his closest teams. Like, 30 year-old little me…I was booking his yacht charters in the South of France, his flight charters across a 5 country voyage with 30 of his closest friends, business associates and family members and delegating helicopter flights from the top of skyscrapers in Manhattan. It was exhilarating and exhausting at the same time because any mistake I made would likely be at least a $50,000 mistake at any given time. There was no time to be complacent. You had to be on the ball every given minute.
So what did I learn from this experience?
I learned first hand what it felt like working with one of the first entrepreneurs in my career who showed me how deeply he cared about his business and the people he worked with.
I learned about the humility he carried throughout his career, even though he was one of the most profound businessmen in the country (and the world).
The kindness he showed me when he didn’t have. People were always around him waiting to give him what he needed, and yet he always said, “please” and “thank you.” He introduced me to every important person that ever walked into his famous 20th floor office and he always, always said, “Have you met Christine? She’s the smartest person you’ll ever meet!” Just literally the kindest and most giving person I had ever worked for.
In 2021, this wonderful entrepreneur passed away peacefully in his bed at home. When I read about his passing, I felt a profound sadness and all the memories of the special moments I remembered came flooding back like it was yesterday. He was kind, funny, warm, and lived for the small moments every day. He visited his grocery stores on weekends and talked to every staff member he could talk to on his special Sunday visits. He welcomed the grade 9 students we invited to our head office when it was “Bring your kids to work day” and they were in awe that he actually came downstairs to the grocery store below our head office to greet the children. “Hi kids!!” he would say, as he walked in on our tour and introduced himself.
This experience was more than 20 years ago but I will never forget the impact he made to those who worked for him. He taught me that being a founder and a leader meant that people chose to work for you. He taught me something really special - that resumes and connections sometimes don’t mean a thing. It’s how hard you work and the great things each person is able to accomplish that makes you great. It’s also the reputation you build by how you treat people. And he truly made me feel great about myself.
So what do I wish I knew in my 30’s if I could go back in time?
Everything happens for a reason and not everything is purely based purely on luck. My chance meeting with this man in a small elevator 20 years ago was probably a bit of luck, but my interaction with him made some sort of imprint on him. It wasn’t just chance that I got to rub shoulders with such a successful entrepreneur. He leaned into my development, trusted me with big responsibilities and he always told me what a great job I was doing. I didn’t believe him but I must have been doing something right because he kept offering me greater opportunities to do big things.
If I could go back in time, I would have told him how much I appreciated his mentorship. I would have accepted all the crazier opportunities he gave me which I declined because I didn’t think I was worthy (even though he didn’t offer those opportunities to his other team members). If I wasn’t so naive and insecure, I would have understood that he could pick and choose to work with anyone he likes, and he chose me. So I should have embraced every opportunity he gave me. I was young, insecure and didn’t feel like I deserved that job. And that was my greatest regret.
My advice to my younger self would have been to embrace what I was given. Lean into it. Enjoy it. The opportunity was given to you because you deserve it.
Today, I try to be the leader that he was when I was young. I try to give opportunities to people who just need to be given a chance to prove themselves. I will never be the leader that he was but I also will never forget the impact he made on me, a small 30 year old wet nosed girl who met this very powerful and kind man in an elevator one day. My memories of him and the opportunities he gave me will never be forgotten and I’m grateful for that fateful day when I was “summoned” to work with such a great, great man.