Why This Lawyer Traded The Courtroom For Coaching

What does it actually take to leave a 20-year legal career and become an executive coach? Jonathan Cullen spent two decades as in-house counsel, including at Pfizer, before making that shift, a decision driven primarily by his son Tristan’s Down syndrome diagnosis. In this episode, he and Nathalie get into the batting-cage discipline of not giving advice even when a client’s begging for it, and what actually separates coaching from mentoring. There’s also the story of the fan email he sent author Greg McKeown that turned into years of work on Greg’s book Effortless. Plus the smallest possible action for building a real friendship: putting an actual phone call on the calendar.

Jonathan Cullen spent two decades practicing law, including years in intellectual property litigation and, later, as in-house counsel at Pfizer, before making a full transition to executive coaching. His shift toward coaching was shaped in large part by the birth of his son, Tristan, who has Down syndrome, an experience that reshaped how Jonathan thought about control and presence, both at home and at work. He now coaches primarily within the legal profession, drawing on his own background to work with lawyers navigating leadership and career transitions of their own. Jonathan also collaborated with author Greg McKeown, contributing research and writing support to McKeown’s book Effortless. He lives with his wife and their two children, Olivia and Tristan, and can be found at jonathancullencoaching.com.

Connect with Jonathan Cullen: LinkedIn

Connect with Coach Academy: canadacoachacademy.com