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Artwork for Lawyer to Leader

Lawyer to Leader

Jonathan Cullen
Speak-Up Culture
Leadership
Law Firms
Inlaws
Chris Ito
Vulnerability
Culture
Introverted Leadership
Curiosity

This show is built around a single question: why do technically brilliant lawyers so rarely break through as strategic leaders? The answer is simpler and more uncomfortable than most lawyers expect: technical excellence is the entry ticket, not the destination. The Lawyer to Leader is the podcast for driven attorneys who have mastered the law and are ready to master the room, the strategy, and the... more

PublishesDailyEpisodes4Founded22 days ago
Number of ListenersCategories
EducationSelf-ImprovementCareersBusiness

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Artwork for Lawyer to Leader

Latest Episodes

Episode Introduction

Most lawyers are trained to have the answer. To advise, fix, and move on. Rebecca Hockin spent years doing exactly that. She was good at it. But something kept drawing her in a different direction. In this episode, Jonathan Cull... more

Episode Introduction

Most lawyers are trained to work alone, grind through problems in silence, and figure out their careers by watching the person above them. Dylan Gibbs saw that model up close, from the Supreme Court of Canada to national litigat... more

Episode Introduction

Most lawyers are trained to have the right answer. Stephen (Shed) Shedletzky argues that the most powerful thing a leader can do is ask the right question and then actually listen. In this episode, Jonathan Cullen sits down with... more

Episode Introduction

Most lawyers are taught to stay on the path. Build the credentials, climb the ladder, collect the titles. But there’s another way, and sometimes it’s good to look outside the professional for a model. Chris Ito did all of that, ... more

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Recent Guests

Rebecca Hockin
Commercial lawyer and executive coach based in Vancouver, British Columbia
Fractional in-house counsel; executive coach
Episode: The Power of Curiosity: Why the Best Lawyers Ask More & Answer Less ft. Rebecca Hockin
Dylan Gibbs
Founder of InLaws, a private community for Canadian lawyers
InLaws
Episode: Running a Modern Law Practice in the AI Era (ft. Dylan Gibbs)
Stephen Shed Shedletzky
Leadership expert, author, speaker; author of Speak-Up Culture
Author of Speak-Up Culture; formerly led igniter team with Simon Sinek
Episode: Building a Speak-Up Culture for Lawyers (ft. Stephen (Shed) Shedletzky)
Chris Ito
Chef, former Google engineer, nonprofit leader
Better Life Foundation; Hope's Corner
Episode: From Google to Nonprofit Chef: One Engineer's Search for a Life of Purpose (ft. Chris Ito)

Chart Rankings

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Apple Podcasts
#182
Canada/Business/Careers

Talking Points

Recent interactions between the hosts and their guests.

From Google to Nonprofit Chef: One Engineer's Search for a Life of Purpose (ft. Chris Ito)
Q: How did you decide to navigate the tension between a prestigious track and your evolving values?
He explains not making a binary choice, paying attention to internal signals, and choosing paths that align with family and personal purpose, even if they require sacrifices. He emphasizes following curiosity and gradually moving toward work that feels meaningful.
Building a Speak-Up Culture for Lawyers (ft. Stephen (Shed) Shedletzky)
Q: What is Speak-Up Culture and why is it important for lawyers?
Speak-Up Culture is an environment that blends psychological safety with a tangible incentive to share ideas, feedback, and concerns because doing so leads to real progress and better outcomes, especially when leaders model vulnerability with proper context.

Audience Metrics

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These podcasts share a similar audience with Lawyer to Leader:

1. Armchair Expert with Dax Shepard
2. Good Hang with Amy Poehler

How many episodes of Lawyer to Leader are there?

Lawyer to Leader launched 22 days ago and published 4 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Lawyer to Leader?

Recent guests on Lawyer to Leader include:

1. Rebecca Hockin
2. Dylan Gibbs
3. Stephen Shed Shedletzky
4. Chris Ito

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