Meet Your Coach
I'VE ALWAYS BEEN A LITTLE DIFFERENT.
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I'm Jonathan Cullen – a husband, special needs dad, lifelong learner, and someone who’s never been afraid to chart a fresh path.
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What Gets Me Up In the Morning
I’m passionate about my family, my health, the gym, and the beautiful game of soccer. And yes, I’ll always make room for a good dad joke along the way.
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I love helping lawyers unlock the best version of themselves – at work and in life.
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I’ve never been content to just “do the job.” I’ve always been curious, always learning, and always looking for an edge. Case law and contracts were great, but I was just as likely to be diving into books and podcasts on management, strategy, decision-making, and leadership.
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I wanted to understand what made people tick. How people truly thrive. And, most importantly, how to help others unleash their hidden potential.
My Hard-Won Lesson
Family is at the center of everything I do.
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I believe that a full career needs to be matched with a full life.
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When my son was born with Down syndrome, we almost lost him in those first fragile months. That experience shook me to my core and reshaped how I see life, work, and resilience.
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Watching him fight and then thrive taught me more about courage, patience, and perspective. It gave me a deep appreciation for what truly matters, and for the strength you can summon when your back is against the wall.
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Being a special needs parent makes me who I am as a coach: empathetic, practical, and focused on helping people find strength they didn’t know they had. Both my children continue to be my greatest teachers, reminding me daily that progress is rarely linear, and that joy often shows up in unexpected places.
The Road I've Traveled
I cut my teeth at a leading international law firm and then for nearly two decades I worked at Pfizer. I led legal teams in Canada, Europe and Latin America through some of the most complex challenges a global business can face, including the COVID-19 pandemic.
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Along the way, I’ve had the good fortune to be recognized as General Counsel of the Year, to become a graduate of the Rotman School of Management/CBA Business Leadership Program for In-House Counsel, and to be featured in outlets like the Financial Post, Canadian Lawyer, and the Association Corporate Counsel for my approach to strategic legal leadership.
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I've also had the incredible opportunity to collaborate with my absolute favorite author Greg McKeown on the New York Times bestseller Effortless: Make It Easier to Do What Matters Most.
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But here’s the throughline of my career: what lit me up most wasn’t just solving legal problems, it was developing legal professionals. Coaching, mentoring, and helping lawyers grow into trusted advisors and leaders is my passion.
Why I'm In Your Corner
I am both a Leadership & Performance Certified Coach (LPCC) and a Certified In-House Counsel (CIC.C). I’m also pursuing my Associate Certified Coach (ACC) credential from the International Coaching Federation (ICF).
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I’ve built a leadership & performance coaching practice designed specifically for high-achieving lawyers and legal teams. My focus: helping smart, ambitious lawyers push through the barriers that stall careers and drain energy. Through one-on-one coaching, small group programs, and team coaching, I help lawyers:
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Grow from expert technicians into strategic, business-savvy advisors
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Build resilience so they thrive without running on empty
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Step confidently into leadership roles and stand out from their peers
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My coaching approach combines the practical tools I used as a GC with my professional coaching training. The result? Coaching that’s both real-world and transformative.
If you want more progress, more influence, and more life, with a lot less burnout, I'd love to partner with you. My goal is simple: help you become unrecognizable from the lawyer you are today, in the best way possible.
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I have helped countless legal professionals just like you transform their careers. Curious as to what this could look like for you or your team? Let’s connect and explore how coaching can accelerate your growth.
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