After decades leading teams and organizations, I’ve realized mentorship isn’t something you outgrow. If anything, it becomes even more important as you move through different phases of life.
What’s surprised me most is that mentorship comes in many forms—coach, teacher, sponsor, accountability partner, challenger, or simply someone who listens. Different people fill those roles at different times. During my years as a CEO, I was surrounded by talented advisors, board members, and colleagues who helped me grow. Some of my most valuable mentoring sessions, though, were with my wife and kids, the ones who often know me better than I know myself.
In this chapter I’m living right now, the need for guidance hasn’t gone away. I still look to mentors, but the questions have changed. It’s less about running a business and more about finding balance, purpose, and a life that makes a lasting difference. Honest feedback and fresh perspectives are just as important today as they’ve ever been. No matter how much experience we collect, we still need people who help us see what we might otherwise miss, push us to stay curious, and remind us that growth doesn’t have an expiration date.
A Way of Life, Not a Program
For me, mentorship has never been a formal program. It’s always been a way of living with curiosity, humility, and a commitment to keep learning.
Take the early years of my career. The trunk of my car was packed with cassette tapes of leadership books I’d listen to on my daily commute. (After a minor fender bender, the police report even noted “over 100 damaged tapes” in the trunk.) Those drives were my classroom. Each mile taught lessons in positivity, consistency, and character, ideas that became the foundation for how I try to lead and live today.
What I didn’t realize at the time was that I was being mentored by voices I’d never met. Those recordings, along with the people I encountered along the way, taught me that talent isn’t fixed. It grows when we stay curious and are willing to learn.
Over the years, I’ve noticed how much our surroundings shape us. In high school and college, I tried to put myself around people I admired, those whose values and standards I hoped to follow. Later in my career, I chose to work with leaders who stretched me, the kind who set expectations that made me raise my own.
It turns out environment can be one of life’s greatest mentors. The places and people we choose to be around quietly influence our habits, our mindset, and what we think is possible. When we put ourselves in spaces that challenge and inspire us, we can’t help but grow.
Over time, I’ve realized all of this applies well beyond work. Joining a health club reminds me daily of the power of community in staying healthy. Being part of a reading group keeps me accountable to learning. Biking with the Zwift app has given me perspective on my own performance, showing how feedback, consistency, and a bit of friendly competition can fuel growth. Traveling exposes me to different cultures and ways of thinking, while time on the water or in nature creates space for reflection and clarity. Conversations over dinner with friends from different vocations broaden my perspective, just as volunteering and mentoring younger people keep me grounded in purpose.
Our environment is a mirror that reflects what we believe is possible. The more we intentionally place ourselves in spaces that challenge, inspire, and renew us, the faster and deeper we grow.
The Mentors Who Shaped Me
I’ve been fortunate to have had mentors at every stage of my journey. Early in my career at Price Waterhouse, a partner took me under his wing. He demanded excellence … precision in the work, responsiveness to clients, and a deep technical understanding. Many of those late nights were uncomfortable and stressful, but they shaped me. They taught me to hold myself to high standards and never compromise on quality. Those lessons became part of who I am.
Years later, a trusted mentor who’s since become a lifelong friend helped me make the leap from CFO to CEO. He saw potential in me before I did. He believed in me, took chances on me, and remains one of my first calls in challenging moments.
I’ve also been mentored by people younger than me or with entirely different expertise. Some of the most impactful in recent years have been those deeply skilled in data and technology, helping me understand how emerging tools like AI could transform healthcare and business. And some of the most powerful lessons came from those closest to the work. Conversations with frontline teammates—those interacting with customers every day—provided insights I could never get from reports or meetings. They reminded me what mattered most: serving people well.
These experiences reinforced that mentorship isn’t hierarchical, it’s reciprocal. You can learn from anyone, regardless of age or title, if you stay humble and curious.
Lessons Learned as Both Mentee and Mentor
Over the years, I’ve found the best lessons in mentorship come quietly through experience, reflection, and honest conversation. Whether I’ve been guided or guiding, a few principles have stayed constant:
- Start with clarity. At different stages of life, we need different mentors. Let your priorities guide who you seek out, so growth isn’t left to chance.
- Stay curious. Titles change, but the need to keep learning never does. Curiosity bridges who we are with who we’re becoming.
- Ask good questions and really listen. The best mentoring conversations aren’t about having all the answers but being fully present. Listening to understand, not to respond, is one of the most powerful leadership skills we can develop.
- Make time. Mentorship doesn’t have to be formal, but it does require intention. A brief call, a shared meal, or a short note can have lasting impact. Over time, those small acts of connection compound into trust.
- Seek truth-tellers. We all need people who will tell us what we need to hear, not just what we want to hear. Honest feedback, given with care, shapes us more than praise ever could.
- Embrace discomfort. Growth rarely happens in our comfort zone. Every meaningful step forward involves risk, experimentation, and the occasional setback. Those moments teach resilience and humility.
From the trunk full of leadership tapes in my twenties to conversations with data scientists and students today, mentorship has been a constant. It’s a reminder that growth never stops and that we become our best selves when we keep learning from one another.
No matter where you are in life, keep asking questions, keep showing up for others. And keep learning.
