I have measured out my career with coffee chats
In November 2023, I had the privilege of attending CIBC’s Global Leadership Team conference as part of a multi-generational career discussion. From an intimate chat with the CEO to the hot seat at a table full of senior executives — people one, two, three levels below him — it was a day of sweaty palms and valuable insights.
After lunch, I walked out with seven coffee chats in my pocket.
I’m not normally one for active networking, but knew this was an opportunity rarely afforded to anyone at this point in my professional journey. So, like any good UX researcher, I got caffeinated, asked a few open questions, and listened hard.
What surprised me
The openness and frankness these executives shared.
All seven had the same quiet confidence about them, a sense of conviction and authenticity tempered by thousands of conversations across their professional years, and it was easy to understand how they had worked their way up the corporate ladder.
I was needlessly nervous about taking up more time than requested.
Despite their strategic firepower and busy schedules, they were surprisingly generous with their time and advice; quite a few of these chats stretched beyond the half hour slots on our Outlook calendars.
Learning and adapting to each person’s coffee chat style was an interesting challenge.
Some preferred clean efficiency, dishing out a decade of business lessons in 30 minutes, while other conversations touched on the edges of our personal lives. All those hours of interviewing users for my job definitely came in handy.
What they taught me
While each person had something different to share, a few common themes kept cropping up:
Be flexibly ambitious.
Our CEO, surrounded by people half his age, challenged us to dream big: thinking beyond the next promotion to sitting in his chair in 20 years.
More realistically, others advised, think strategically in the medium-term: set your direction and then take action. Take note of 2–3 positions to aim for, consider the skills still required, and work on strengthening those areas. You might find yourself naturally gravitating to one or the other, but you’ll end up with the capabilities to do both.
This is especially prudent early in your career or at the bottom of an organization, where you have the most flexibility to move around and fill gaps in expertise. As you advance through different opportunities, examine whether each step is in your preferred direction and how it helps you grow.
Find a cause.
The benefit of this advice was twofold: to (a) balance your life beyond work and (b) expand your network.
A career is a marathon, not a sprint, and having ways to disconnect and recharge is key for staying the distance. Finding a passion pushes you to define yourself by more than your professional identity, crucial as that may be in today’s society. Every person I talked to had their own form of carving out balance, from staying in touch with community issues to gymming as a treat to just good ol’ basic self-care.
Additionally, reaching out broadly exposes you to new ideas and influences you wouldn’t find otherwise in the comfort of your own office. We maximize our potential through other people, and creativity and support can come from the most unexpected of places.
Be confidently proactive for the people who believe in you.
If you put your hand up for initiatives against all fear of self-doubt, that already sets you apart from most. In the face of imposter syndrome and identity-related pressures in the workplace (gender, ethnicity, or otherwise), it’s even more important to show up with receipts, to air out your voice, and to be thoughtful with your words.
Get comfortable being uncomfortable; just a touch of stress is healthy motivation to keep moving forwards. This is where proactive curiosity for yourself is vital, in the form of active check-ins and iterative feedback from your manager and colleagues.
Look for opportunities to add value and communicate your efforts, especially after you’ve had a few years under your belt. Effective leaders will place you in the right spotlights to amplify your influence. Cherish those who consistently demonstrate confidence in you to do the work you do.
At the same time, don’t stress too much.
Maximize your efforts where you are and the rest will follow. Staying consistent over the long-term, day in and day out, and focusing on continual growth is the key.
And most importantly, stay human.
Though it can be tricky to balance the personal and professional spheres, authentic empathy and vulnerability go a long way in helping others help you. Prioritize people before process.
What’s next?
So there you have it, the secrets of seven coffee chats spilled.
Going through these conversations challenged how I view and approach my career. It’s easy to be tranquilized by the trivial, the day-to-day tasks at hand. These coffee chats were a welcome wake-up call to start sculpting my future and taking action to make it happen.
I’m ever more grateful for the mentors in my life and the teams I’ve belonged to. Now solidly into 2024, I’ve already become more intentional with my time, energy, and planning, and it’s made all the difference.
As Sir Terry Pratchett would say, make the present a past worth having.
A sincere thank you to Afshan Ali, Robin Brent, Shrawan Garladinne, Richard Jardim, Christina Kramer, Atanaska Novakova, and Robert Sedran for your time, experience, and advice. Onwards and upwards.
