The Diary of a CPO - Chapter 12
The Entrepreneurial Journey
I’m currently on a much-needed vacation. I’m staring into the vast ocean of blue and having a real opportunity to look back in hindsight at my career which has spanned over 20 years.
I started my career in formal corporations, working at the companies that we’ve all heard of. The global matrix organizations that have fancy titles like “Centre of Excellence” which employ hundreds of thousands of employees (when I worked at Loblaw Companies Ltd they were the largest private employer in Canada with 185,000 employees - today they are over 280,000). While that definitely wasn’t my cup of tea, I also had an opportunity to work with really amazing people and leaders. It was also the chapter in my life where I got married, signed up for an awesome ESOP program which allowed me to gain my first mortgage, and allowed me to participate in a parental leave top-up program when I had my 2 kids. I remember a startup CEO that once said, “Knowing your work ethic, Christine, I bet when you had your kids, you only took 2 weeks of mat leave and came right back to work!” No, not true. I took a full year off for my first leave and then I took 2 years off for my second when taking leave beyond 12 months was unheard of in the Canadian employment landscape. The reality is when I do something, I do it all the way and I do it really well. That includes how I take care of my family and raise my kids. I’m not just good at my job, I’m great at raising a family.
The last 10 years of work has been working at startups of all sizes and maturity. Let me tell you, it’s been a ride. I’ve worked with founders and CEOs of all backgrounds and personalities. I’ve had the privilege of working alongside so many leaders that I respected and admired and they taught me so much about building a business as well. I learned to become a very well rounded leader, building HR teams outside of the HR norm and focusing more on outcomes versus governance and rules. Did we take risks as a company and an HR team? For sure we did, but no business worth building becomes great playing by strict rules. I was an HR leader that broke almost every rule that HR was told never to break, and I really enjoyed doing that. I also had the privilege of building the best teams over the last decade. Not everyone agreed with all the decisions I made, but I didn’t make decisions to be popular. I did what was right and that wasn’t always easy.
Now, as I look back and realize that I am leaving this phase of my life as an “employee” forever, I feel a sense of gratitude and in some sense, relief. I know this was the path that I was designed to take and I know this is my time. Branching off to do “my own thing” feels right for me and it’s changed how I view relationships with the people I choose to work with.
Choosing who you decide to work with is an incredibly empowering feeling because you no longer need to work with people that don’t align with your values. I’ve never been someone you would describe as “fluffy” or full of feelings but I’ve always understood what it means to have integrity, even when I’m operating at the highest level of performance. So here’s the playbook I’ve always operated with when I work with people, regardless if I’m an individual contributor, a leader or a business owner. Not much has changed over the past 20 years being an operator and my guess is, not much will change as I complete this last ⅓ of my career moving into entrepreneurship, so here are a few reflections I have as I sit and look at the beautiful blue water ahead of me.
Integrity means being honest with people, even when you’re sharing tough news. They don’t have to agree with your decision, but you do need to treat people with respect and integrity and that often starts with being honest with them. A lot of leaders I’ve worked with claimed they were honest and radically candid, but really, they were not. They were often “obnoxiously aggressive” or “ruinously empathetic.” Have courage and speak the truth. People will respect you for that.
Don’t stay where you’re not respected. If the people you work the most closely with don’t respect the work you do and how you operate, they never will no matter how hard you try. You know that feeling, I don’t have to explain it to you. There are many jobs, different bosses and tons of ways to make money out there. You don’t have to settle and be disrespected for years. Life is not worth living that way because it truly changes you as a person and youth is too fleeting to be unhappy for so long. Choose to be respected.
Being performance oriented is the dream of every leader. The best leaders will challenge you to perform at your best. Greatness never came out of “easy” but there’s a way to motivate people and inspire them to do things they never would have believed in themselves. So ensure your leader is motivating you, not constantly demanding from you. Think about who you would want to be with if your life depended on it - would you trust your current leaders if you were in a life and death situation? I choose only those who would fight to pay my ransom.
Think about how you feel at the end of the day when you come home exhausted and completely spent. Ask yourself, have you made an impact and moved the needle based on all the effort you exerted? Are you proud of your work and the results? There’s effort that leads to results and there’s plain hard work that sometimes never makes a dent. Working smarter, not harder is actually a thing - are you and the team actually working smarter? Results don’t lie.
Do you think about your relationships with the people you work with. For me, work is more than just a job. The people I work with are in the trenches with me so the relationships I’ve built with many of these team members have continued even after decades have passed. Do you have relationships with team members in this way? Would they step up for you if you called them today?
Have you ever felt the mood of the team you work with? I’ve worked in really hard environments. The earlier stage of the startup, the harder the work was because no one knew the company you were working at, you often had a shoestring budget and you had to really roll up your sleeves because you had a bootstrapped team. No doubt, those were hard environments to work in, but our team knew how to have fun! We worked long hours, did hard things and truly struggled (i.e., our restaurant software company revenue went to zero during the height of COVID when the government shut down all restaurants in the country). We laughed, sometimes we cried, but we always felt good around one another. Honestly, if you’re going to spend 80 hour weeks with people, you should genuinely want to be around them a lot.
What do people say about you when you’re not in the room? I ask this to almost everyone I know. Do you have a clue what people say about you when you’re not around? I’ve had many people in my network literally call me to say xx said this about you whether on stage, in a group networking dinner or to a potential business partner. I’m not surprised by what they say, but I am choked up sometimes.
There’s the old Netflix rule about their talent development process whereby they get managers to answer this one question about people on their team, "Knowing everything I know today, would I hire this employee again?" If the answer is no, they believe it's fairer to everyone to part ways. Fair. So do you also gauge and measure your managers every year and ask yourself if you could work with this leader again, would you? If the answer is no, chances are they either feel the same way about you or they have no idea you are that unhappy…is this how quiet quitting started?
Every company has rules. Some rules are meant to keep the peace and scale a company, but some rules are just plain dumb and you have to accept it or be labeled a trouble maker. The reality is, someone made the rule, often in management (CEO or founder) or HR, because either someone more stupid than you broke the peace and a new rule had to be implemented to ensure chaos didn’t reign in or there was a weird rule that leadership believed in and they implemented it because they could. I know I’m a leader and I’m also in HR, but I really despise a lot of rules that are made at companies. How do you feel about them? If I don’t love rules, I guess I wasn’t meant to be part of a big company.
Lastly, I know more than anyone that oftentimes a job is more than a paycheck…but money actually does make the world go around. It may not buy happiness, but it sure feels better to cry in a Ferrari than in a dingy subway platform, broke and hungry. So I’ve often asked the highest performers, if you’re so high performing, are you getting what you deserve? Because the reality is, companies live off budgets and if you know anything about the dreaded “bell curve,” you will probably earn anywhere between 2% to 6% each year in salary increases unless you plan to leave your company every couple of years to make a jump in salary increase with each move. Does that inspire you based on how much effort and time you put into your job?
The list above are just a few of my random thoughts that have become my playbook over the years. I think it was written to plan my move away from “company” and more towards “entrepreneurship.” People say to go out on your own is to take on a big risk and it’s not worth it but to be honest, I think it’s worse to stay in a box that no longer fits. I’m not afraid of taking risks or trying new things and chances are, this whole journey could be a flop for me but I’m willing to go all in to find out because unless I try, I’ll truly never know.
So what’s next for me? Going all in with 5 to 9 Society, an exclusive, invite-only networking community that will bring Investors, Founders/CEOs and vetted High Potential Operators together. Expect job/candidate matching for coveted roles, exclusive dinners and events, along with advisory/coaching and referrals to support growing businesses. The website is currently getting ready to launch along with the first group of vetted cohorts who will be the founding members for this exclusive network. I may even start my own Tik Tok and podcast. To my awesome network, stay tuned and follow me for more insights. I just may need to change the name of my Substack now that I’m a recovering Chief People Officer…
Thanks for reading. Glad to have you as part of my journey and don’t forget to follow to learn more about this new venture!
Many rules are dumb and people need to be more open to rethinking things that may have worked at one point but do not serve the company culture anymore.
This list totally resonates. Thank you!