I’ve received thousands of heartfelt messages after announcing the end of my role as an Engineering Manager at Loblaw Digital. I’m so impressed. I’m truly grateful and impressed by your kindness and support. As a way of giving back to the community, I’d like to share some insights and leadership secrets gained from my own experiences and interactions with tech leaders from Amazon Google NVIDIA.

Choose who you work for. Your most important role in life is as a spouse; the second most important is who you work for. You might feel you can’t choose your boss—for example, I’ve previously reported to a director and wondered how I could choose differently. In reality, I chose to work for our retailer clients by adding value to their experiences. I chose to empower merchandising teams by enriching product, category, and campaign data. I chose to make working with my team less stressful and more enjoyable. Communicate your choices clearly with your manager. If you still feel trapped in your current situation, challenge yourself to think bigger and explore opportunities outside the box.

Take risks, face challenges, and embrace failure early. Once you’re clear about who you’re working for, don’t shy away from risks. Whenever I meet new tech professionals, I ask about the challenges they face. If someone says they face no challenges or prefers not to share, I see a red flag. When my code-generation agent was still in its infancy, I paid out-of-pocket to experiment and demonstrate value to leadership. My biggest regret was not fully leveraging the playground environment I prepared for my teams. If you’re stuck repeating the same patterns, proactively disrupt yourself before someone else does. For example, one backend team initially dismissed LLM-generated code as useless. Upon closer inspection, it became clear their repetitive work patterns prevented them from benefiting. Mistakes are part of growth. As a leader, allowing your team the autonomy to make decisions and learn from their failures is an art form.

If your team’s morale is low, reflect on the above two points first.

Show empathy and respect. I might be known as the one who says “thank you” and “sorry” most frequently in teams. Acknowledge your limitations and respect your team’s boundaries. Unrealistic demands, such as expecting a feature delivery in three days without understanding velocity, budget, or cost, show a lack of empathy. Instead, openly share challenges, show appreciation for all suggestions—even those initially seeming unhelpful—and genuinely apologize for your own mistakes. People won’t remember every mistake, but they’ll remember how you handled them. Always give credit to your team when presenting their work.

As your career progresses from engineer to manager, director, or CTO, your impact may multiply significantly, but your personal workload won’t scale equally. Focus more strategically on long-term goals, vision, and balanced decisions is the only way to scale up your work. If you seek control, think strategically about how data flows within your business. For example, my previous CTO successfully improved our entire eCommerce platform by developing an IAM service that centrally managed authorization. Similarly, a senior director effectively boosted team productivity by setting strategic goals around exploring GenAI technologies. These types of initiatives significantly elevate the strategic value of technology within a business.